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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Discovery</span> </div> </a> <ul id="toc-Discovery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ring_formula" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ring_formula"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Ring formula</span> </div> </a> <ul id="toc-Ring_formula-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Early_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Early_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Early applications</span> </div> </a> <ul id="toc-Early_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>Occurrence</span> </div> </a> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Benzene_derivatives" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Benzene_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Benzene derivatives</span> </div> </a> <ul id="toc-Benzene_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Catalytic_reforming" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Catalytic_reforming"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Catalytic reforming</span> </div> </a> <ul id="toc-Catalytic_reforming-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toluene_hydrodealkylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toluene_hydrodealkylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Toluene hydrodealkylation</span> </div> </a> <ul id="toc-Toluene_hydrodealkylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toluene_disproportionation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toluene_disproportionation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Toluene disproportionation</span> </div> </a> <ul id="toc-Toluene_disproportionation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Steam_cracking" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Steam_cracking"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Steam cracking</span> </div> </a> <ul id="toc-Steam_cracking-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Other methods</span> </div> </a> <ul id="toc-Other_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Component_of_gasoline" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Component_of_gasoline"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Component of gasoline</span> </div> </a> <ul id="toc-Component_of_gasoline-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Sulfonation,_chlorination,_nitration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sulfonation,_chlorination,_nitration"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Sulfonation, chlorination, nitration</span> </div> </a> <ul id="toc-Sulfonation,_chlorination,_nitration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrogenation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrogenation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Hydrogenation</span> </div> </a> <ul id="toc-Hydrogenation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal_complexes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_complexes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Metal complexes</span> </div> </a> <ul id="toc-Metal_complexes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Health_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Health effects</span> </div> </a> <ul id="toc-Health_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Exposure_to_benzene" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Exposure_to_benzene"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Exposure to benzene</span> </div> </a> <button aria-controls="toc-Exposure_to_benzene-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Exposure to benzene subsection</span> </button> <ul id="toc-Exposure_to_benzene-sublist" class="vector-toc-list"> <li id="toc-Benzene_exposure_limits" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Benzene_exposure_limits"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Benzene exposure limits</span> </div> </a> <ul id="toc-Benzene_exposure_limits-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Toxicology</span> </div> </a> <ul id="toc-Toxicology-sublist" class="vector-toc-list"> <li id="toc-Biomarkers_of_exposure" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Biomarkers_of_exposure"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.1</span> <span>Biomarkers of exposure</span> </div> </a> <ul id="toc-Biomarkers_of_exposure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biotransformations" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Biotransformations"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.2</span> <span>Biotransformations</span> </div> </a> <ul id="toc-Biotransformations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Molecular_toxicology" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Molecular_toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.3</span> <span>Molecular toxicology</span> </div> </a> <ul id="toc-Molecular_toxicology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_oxidation_and_carcinogenic_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Biological_oxidation_and_carcinogenic_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.4</span> <span>Biological oxidation and carcinogenic activity</span> </div> </a> <ul id="toc-Biological_oxidation_and_carcinogenic_activity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Routes_of_exposure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Routes_of_exposure"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3</span> <span>Routes of exposure</span> </div> </a> <ul id="toc-Routes_of_exposure-sublist" class="vector-toc-list"> <li id="toc-Inhalation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Inhalation"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3.1</span> <span>Inhalation</span> </div> </a> <ul id="toc-Inhalation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Exposure_from_soft_drinks" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Exposure_from_soft_drinks"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3.2</span> <span>Exposure from soft drinks</span> </div> </a> <ul id="toc-Exposure_from_soft_drinks-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Contamination_of_water_supply" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Contamination_of_water_supply"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3.3</span> <span>Contamination of water supply</span> </div> </a> <ul id="toc-Contamination_of_water_supply-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Genocide" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Genocide"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3.4</span> <span>Genocide</span> </div> </a> <ul id="toc-Genocide-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Explanatory_notes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Explanatory_notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Explanatory notes</span> </div> </a> <ul id="toc-Explanatory_notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Benzene</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 88 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-88" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">88 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Benseen" title="Benseen – Afrikaans" lang="af" hreflang="af" data-title="Benseen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%D9%8A%D9%86_(%D9%85%D8%B1%D9%83%D8%A8_%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A6%D9%8A)" title="بنزين (مركب كيميائي) – Arabic" lang="ar" hreflang="ar" data-title="بنزين (مركب كيميائي)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Benzeno" title="Benzeno – Aragonese" lang="an" hreflang="an" data-title="Benzeno" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Bencenu" title="Bencenu – Asturian" lang="ast" hreflang="ast" data-title="Bencenu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Benzol" title="Benzol – Azerbaijani" lang="az" hreflang="az" data-title="Benzol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AC%E0%A7%87%E0%A6%A8%E0%A6%9C%E0%A6%BF%E0%A6%A8" title="বেনজিন – Bangla" lang="bn" hreflang="bn" data-title="বেনজিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Benzene" title="Benzene – Minnan" lang="nan" hreflang="nan" data-title="Benzene" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Bashkir" lang="ba" hreflang="ba" data-title="Бензол" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Belarusian" lang="be" hreflang="be" data-title="Бензол" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%91%D1%8D%D0%BD%D0%B7%D0%BE%D0%BB" title="Бэнзол – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Бэнзол" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Benzene" title="Benzene – Central Bikol" lang="bcl" hreflang="bcl" data-title="Benzene" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Bulgarian" lang="bg" hreflang="bg" data-title="Бензен" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Benzen" title="Benzen – Bosnian" lang="bs" hreflang="bs" data-title="Benzen" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Benz%C3%A8" title="Benzè – Catalan" lang="ca" hreflang="ca" data-title="Benzè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Benzen" title="Benzen – Czech" lang="cs" hreflang="cs" data-title="Benzen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Bensen" title="Bensen – Welsh" lang="cy" hreflang="cy" data-title="Bensen" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Benzen" title="Benzen – Danish" lang="da" hreflang="da" data-title="Benzen" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Benzol" title="Benzol – German" lang="de" hreflang="de" data-title="Benzol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Benseen" title="Benseen – Estonian" lang="et" hreflang="et" data-title="Benseen" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%92%CE%B5%CE%BD%CE%B6%CF%8C%CE%BB%CE%B9%CE%BF" title="Βενζόλιο – Greek" lang="el" hreflang="el" data-title="Βενζόλιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Benceno" title="Benceno – Spanish" lang="es" hreflang="es" data-title="Benceno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Benzeno" title="Benzeno – Esperanto" lang="eo" hreflang="eo" data-title="Benzeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Bentzeno" title="Bentzeno – Basque" lang="eu" hreflang="eu" data-title="Bentzeno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%D9%86" title="بنزن – Persian" lang="fa" hreflang="fa" data-title="بنزن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://fr.wikipedia.org/wiki/Benz%C3%A8ne" title="Benzène – French" lang="fr" hreflang="fr" data-title="Benzène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Beins%C3%A9in" title="Beinséin – Irish" lang="ga" hreflang="ga" data-title="Beinséin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Benceno" title="Benceno – Galician" lang="gl" hreflang="gl" data-title="Benceno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B2%A4%EC%A0%A0" title="벤젠 – Korean" lang="ko" hreflang="ko" data-title="벤젠" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Benzene" title="Benzene – Hausa" lang="ha" hreflang="ha" data-title="Benzene" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target"><span>Hausa</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B2%D5%A5%D5%B6%D5%A6%D5%B8%D5%AC" title="Բենզոլ – Armenian" lang="hy" hreflang="hy" data-title="Բենզոլ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AC%E0%A5%87%E0%A4%82%E0%A4%9C%E0%A5%80%E0%A4%A8" title="बेंजीन – Hindi" lang="hi" hreflang="hi" data-title="बेंजीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Benzen" title="Benzen – Croatian" lang="hr" hreflang="hr" data-title="Benzen" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Benzena" title="Benzena – Indonesian" lang="id" hreflang="id" data-title="Benzena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Bensen" title="Bensen – Icelandic" lang="is" hreflang="is" data-title="Bensen" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Benzene" title="Benzene – Italian" lang="it" hreflang="it" data-title="Benzene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%91%D7%A0%D7%96%D7%9F" title="בנזן – Hebrew" lang="he" hreflang="he" data-title="בנזן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%AC%E0%B3%86%E0%B2%82%E0%B2%9C%E0%B3%80%E0%B2%BC%E0%B2%A8%E0%B3%8D" title="ಬೆಂಜೀ಼ನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಬೆಂಜೀ಼ನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%91%E1%83%94%E1%83%9C%E1%83%96%E1%83%9D%E1%83%9A%E1%83%98" title="ბენზოლი – Georgian" lang="ka" hreflang="ka" data-title="ბენზოლი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Kazakh" lang="kk" hreflang="kk" data-title="Бензол" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Kyrgyz" lang="ky" hreflang="ky" data-title="Бензол" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Benzenum" title="Benzenum – Latin" lang="la" hreflang="la" data-title="Benzenum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Benzols" title="Benzols – Latvian" lang="lv" hreflang="lv" data-title="Benzols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Benzol" title="Benzol – Luxembourgish" lang="lb" hreflang="lb" data-title="Benzol" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Benzenas" title="Benzenas – Lithuanian" lang="lt" hreflang="lt" data-title="Benzenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Benzeen" title="Benzeen – Limburgish" lang="li" hreflang="li" data-title="Benzeen" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Benzen" title="Benzen – Lombard" lang="lmo" hreflang="lmo" data-title="Benzen" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Benzol" title="Benzol – Hungarian" lang="hu" hreflang="hu" data-title="Benzol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Macedonian" lang="mk" hreflang="mk" data-title="Бензен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AC%E0%B5%86%E0%B5%BB%E0%B4%B8%E0%B5%80%E0%B5%BB" title="ബെൻസീൻ – Malayalam" lang="ml" hreflang="ml" data-title="ബെൻസീൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Benzena" title="Benzena – Malay" lang="ms" hreflang="ms" data-title="Benzena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Benzeen" title="Benzeen – Dutch" lang="nl" hreflang="nl" data-title="Benzeen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%99%E3%83%B3%E3%82%BC%E3%83%B3" title="ベンゼン – Japanese" lang="ja" hreflang="ja" data-title="ベンゼン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Benzen" title="Benzen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Benzen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Benzen" title="Benzen – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Benzen" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Benz%C3%A8n" title="Benzèn – Occitan" lang="oc" hreflang="oc" data-title="Benzèn" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Benzol" title="Benzol – Uzbek" lang="uz" hreflang="uz" data-title="Benzol" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%AC%E0%A9%88%E0%A8%A8%E0%A8%9C%E0%A8%BC%E0%A9%80%E0%A8%A8" title="ਬੈਨਜ਼ੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਬੈਨਜ਼ੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A8%DB%8C%D9%86%D8%B2%DB%8C%D9%86" title="بینزین – Western Punjabi" lang="pnb" hreflang="pnb" data-title="بینزین" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Benzen" title="Benzen – Polish" lang="pl" hreflang="pl" data-title="Benzen" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Benzeno" title="Benzeno – Portuguese" lang="pt" hreflang="pt" data-title="Benzeno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://ro.wikipedia.org/wiki/Benzen" title="Benzen – Romanian" lang="ro" hreflang="ro" data-title="Benzen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Russian" lang="ru" hreflang="ru" data-title="Бензол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Benzene" title="Benzene – Scots" lang="sco" hreflang="sco" data-title="Benzene" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Benzeni" title="Benzeni – Albanian" lang="sq" hreflang="sq" data-title="Benzeni" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%B6%E0%B7%99%E0%B6%B1%E0%B7%8A%E0%B7%83%E0%B7%93%E0%B6%B1%E0%B7%8A" title="බෙන්සීන් – Sinhala" lang="si" hreflang="si" data-title="බෙන්සීන්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Benzene" title="Benzene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Benzene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Benz%C3%A9n" title="Benzén – Slovak" lang="sk" hreflang="sk" data-title="Benzén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://sl.wikipedia.org/wiki/Benzen" title="Benzen – Slovenian" lang="sl" hreflang="sl" data-title="Benzen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A8%DB%95%D9%86%D8%B2%DB%8C%D9%86_(%D8%A6%DB%95%DA%B5%D9%82%DB%95)" title="بەنزین (ئەڵقە) – Central Kurdish" lang="ckb" hreflang="ckb" data-title="بەنزین (ئەڵقە)" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Serbian" lang="sr" hreflang="sr" data-title="Бензен" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Benzen" title="Benzen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Benzen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/B%C3%A9nz%C3%A9na" title="Bénzéna – Sundanese" lang="su" hreflang="su" data-title="Bénzéna" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Bentseeni" title="Bentseeni – Finnish" lang="fi" hreflang="fi" data-title="Bentseeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Bensen" title="Bensen – Swedish" lang="sv" hreflang="sv" data-title="Bensen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%86%E0%AE%A9%E0%AF%8D%E0%AE%9A%E0%AF%80%E0%AE%A9%E0%AF%8D" title="பென்சீன் – Tamil" lang="ta" hreflang="ta" data-title="பென்சீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/Benzol" title="Benzol – Tatar" lang="tt" hreflang="tt" data-title="Benzol" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AC%E0%B1%86%E0%B0%82%E0%B0%9C%E0%B1%80%E0%B0%A8%E0%B1%8D" title="బెంజీన్ – Telugu" lang="te" hreflang="te" data-title="బెంజీన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%9A%E0%B8%99%E0%B8%8B%E0%B8%B5%E0%B8%99" title="เบนซีน – Thai" lang="th" hreflang="th" data-title="เบนซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Бензол – Tajik" lang="tg" hreflang="tg" data-title="Бензол" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Benzen" title="Benzen – Turkish" lang="tr" hreflang="tr" data-title="Benzen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B5%D0%BD" title="Бензен – Ukrainian" lang="uk" hreflang="uk" data-title="Бензен" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%DB%8C%D9%86" title="بنزین – Urdu" lang="ur" hreflang="ur" data-title="بنزین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Benzen" title="Benzen – Vietnamese" lang="vi" hreflang="vi" data-title="Benzen" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E8%8B%AF" title="苯 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="苯" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Benzeno" title="Benzeno – Waray" lang="war" hreflang="war" data-title="Benzeno" data-language-autonym="Winaray" data-language-local-name="Waray" 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Hydrocarbon compound</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the chemical compound. For other uses, see <a href="/wiki/Benzene_(disambiguation)" class="mw-disambig" title="Benzene (disambiguation)">Benzene (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Petroleum_benzine" title="Petroleum benzine">Petroleum benzine</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Benzene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Benzene-3D-vdW.png" class="mw-file-description" title="Benzene molecule"><img alt="Benzene molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Benzene-3D-vdW.png/150px-Benzene-3D-vdW.png" decoding="async" width="150" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Benzene-3D-vdW.png/225px-Benzene-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/Benzene-3D-vdW.png/300px-Benzene-3D-vdW.png 2x" data-file-width="1100" data-file-height="981" /></a><figcaption>Benzene molecule</figcaption></figure><div style="text-align:center;">Space-filling model</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Benzene_geometrie_(2).svg" class="mw-file-description" title="Skeletal formula detail of benzene."><img alt="Skeletal formula detail of benzene." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Benzene_geometrie_%282%29.svg/130px-Benzene_geometrie_%282%29.svg.png" decoding="async" width="130" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Benzene_geometrie_%282%29.svg/195px-Benzene_geometrie_%282%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Benzene_geometrie_%282%29.svg/260px-Benzene_geometrie_%282%29.svg.png 2x" data-file-width="96" data-file-height="112" /></a><figcaption>Skeletal formula detail of benzene.</figcaption></figure><div style="text-align:center">Geometry</div> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Benzene-aromatic-3D-balls.png" class="mw-file-description" title="Benzene ball-and-stick model"><img alt="Benzene ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Benzene-aromatic-3D-balls.png/125px-Benzene-aromatic-3D-balls.png" decoding="async" width="125" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Benzene-aromatic-3D-balls.png/188px-Benzene-aromatic-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Benzene-aromatic-3D-balls.png/250px-Benzene-aromatic-3D-balls.png 2x" data-file-width="995" data-file-height="1100" /></a><figcaption>Benzene ball-and-stick model</figcaption></figure><div style="text-align:center">Ball and stick model</div> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Benzene_sample.jpg" class="mw-file-description" title="Sample of benzene"><img alt="Sample of benzene" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Benzene_sample.jpg/250px-Benzene_sample.jpg" decoding="async" width="200" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Benzene_sample.jpg/330px-Benzene_sample.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Benzene_sample.jpg/500px-Benzene_sample.jpg 2x" data-file-width="1369" data-file-height="1505" /></a><figcaption>Sample of benzene</figcaption></figure><div style="text-align:center;">Benzene at room temperature</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Benzene<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Benzol <i>(historic/German)</i><br />Cyclohexa-1,3,5-triene; 1,3,5-Cyclohexatriene (theoretical resonance isomers)<br />[6]Annulene (not recommended<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>)<br />Phene <i>(historic)</i></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=71-43-2">71-43-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccccc1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16716">CHEBI:16716</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL277500">ChEMBL277500</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.236.html">236</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.685">100.000.685</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2270#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>200-753-7</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01407">C01407</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/241">241</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>CY1400000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/J64922108F">J64922108F</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3039242">DTXSID3039242</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2270#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: UHOVQNZJYSORNB-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">c1ccccc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>6</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001781140000000000♠"></span>78.114</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>sweet aromatic </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.8765(20) g/cm<sup>3</sup><sup id="cite_ref-handbook13_2-0" class="reference"><a href="#cite_note-handbook13-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>5.53 °C (41.95 °F; 278.68 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>80.1 °C (176.2 °F; 353.2 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>1.53 g/L (0 °C)<br /> 1.81 g/L (9 °C)<br /> 1.79 g/L (15 °C)<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><br /> 1.84 g/L (30 °C)<br /> 2.26 g/L (61 °C)<br /> 3.94 g/L (100 °C)<br /> 21.7 g/kg (200 °C, 6.5 MPa)<br /> 17.8 g/kg (200 °C, 40 MPa)<sup id="cite_ref-chemister_6-0" class="reference"><a href="#cite_note-chemister-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>, <a href="/wiki/Chloroform" title="Chloroform">CHCl<sub>3</sub></a>, <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">CCl<sub>4</sub></a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a><sup id="cite_ref-chemister_6-1" class="reference"><a href="#cite_note-chemister-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanediol" class="mw-redirect" title="Ethanediol">ethanediol</a> </td> <td>5.83 g/100 g (20 °C)<br /> 6.61 g/100 g (40 °C)<br /> 7.61 g/100 g (60 °C)<sup id="cite_ref-chemister_6-2" class="reference"><a href="#cite_note-chemister-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a> </td> <td>52 g/100 g (20 °C)<sup id="cite_ref-chemister_6-3" class="reference"><a href="#cite_note-chemister-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>2.13 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>12.7 kPa (25 °C)<br /> 24.4 kPa (40 °C)<br /> 181 kPa (100 °C)<sup id="cite_ref-nist_7-0" class="reference"><a href="#cite_note-nist-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">Conjugate acid</a> </td> <td><a href="/wiki/Benzenium" class="mw-redirect" title="Benzenium">Benzenium</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/w/index.php?title=Arenide_ion&action=edit&redlink=1" class="new" title="Arenide ion (page does not exist)">Benzenide</a><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>255 nm </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−54.8·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.5011 (20 °C)<br /> 1.4948 (30 °C)<sup id="cite_ref-chemister_6-4" class="reference"><a href="#cite_note-chemister-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.7528 <a href="/wiki/Poise_(unit)" title="Poise (unit)">cP</a> (10 °C)<br /> 0.6076 cP (25 °C)<br /> 0.4965 cP (40 °C)<br /> 0.3075 cP (80 °C) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td><a href="/wiki/Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry">Trigonal planar</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>0 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>134.8 J/mol·K </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>173.26 J/mol·K<sup id="cite_ref-nist_7-1" class="reference"><a href="#cite_note-nist-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>48.7 kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−3267.6 kJ/mol<sup id="cite_ref-nist_7-2" class="reference"><a href="#cite_note-nist-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>potential occupational carcinogen, flammable </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><sup id="cite_ref-sigma_10-0" class="reference"><a href="#cite_note-sigma-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H304: May be fatal if swallowed and enters airways">H304</abbr>, <abbr class="abbr" title="H305: May be harmful if swallowed and enters airways">H305</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H340: May cause genetic defects">H340</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</abbr>, <abbr class="abbr" title="H372: Causes damage to organs through prolonged or repeated exposure">H372</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr><sup id="cite_ref-sigma_10-1" class="reference"><a href="#cite_note-sigma-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P331: Do NOT induce vomiting.">P331</abbr><sup id="cite_ref-sigma_10-2" class="reference"><a href="#cite_note-sigma-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_9a02d12247c3a88a" /></span><map name="ImageMap_9a02d12247c3a88a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−11.63 °C (11.07 °F; 261.52 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>497.78 °C (928.00 °F; 770.93 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.2–7.8% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>930 mg/kg (rat, oral)<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>44,000 ppm (rabbit, 30 min)<br />44,923 ppm (dog)<br />52,308 ppm (cat)<br />20,000 ppm (human, 5 min)<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 1 ppm, ST 5 ppm<sup id="cite_ref-PGCH_11-0" class="reference"><a href="#cite_note-PGCH-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>Ca TWA 0.1 ppm ST 1 ppm<sup id="cite_ref-PGCH_11-1" class="reference"><a href="#cite_note-PGCH-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>500 ppm<sup id="cite_ref-PGCH_11-2" class="reference"><a href="#cite_note-PGCH-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.hmdb.ca/system/metabolites/msds/000/001/365/original/HMDB01505.pdf?1358893540">HMDB</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Toluene" title="Toluene">Toluene</a><br /> <a href="/wiki/Borazine" title="Borazine">Borazine</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Benzene_(data_page)" title="Benzene (data page)">Benzene (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464365865&page2=Benzene">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Benzene</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic</a> <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the <a href="/wiki/Chemical_formula#Molecular_formula" title="Chemical formula">molecular formula</a> C<sub>6</sub>H<sub>6</sub>. The benzene <a href="/wiki/Molecule" title="Molecule">molecule</a> is composed of six <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms joined in a planar hexagonal <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> with one <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom attached to each. Because it contains only <a href="/wiki/Carbon" title="Carbon">carbon</a> and hydrogen atoms, benzene is classed as a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>. </p><p>Benzene is a natural constituent of <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> and is one of the elementary <a href="/wiki/Petrochemical" title="Petrochemical">petrochemicals</a>. Due to the cyclic continuous <a href="/wiki/Pi_bond" title="Pi bond">pi bonds</a> between the carbon atoms, benzene is classed as an <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbon</a>. Benzene is a colorless and highly <a href="/wiki/Combustibility_and_flammability" title="Combustibility and flammability">flammable</a> liquid with a sweet smell, and is partially responsible for the aroma of <a href="/wiki/Gasoline" title="Gasoline">gasoline</a>. It is used primarily as a <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> to the manufacture of chemicals with more complex structures, such as <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a> and <a href="/wiki/Cumene" title="Cumene">cumene</a>, of which billions of kilograms are produced annually. Although benzene is a major <a href="/wiki/Chemical_industry" title="Chemical industry">industrial chemical</a>, it finds limited use in consumer items because of its toxicity. Benzene is a <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compound</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Benzene is classified as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>. Its particular effects on <a href="/wiki/Human_health" class="mw-redirect" title="Human health">human health</a>, such as the long-term results of accidental exposure, have been reported on by news organizations such as <i><a href="/wiki/The_New_York_Times" title="The New York Times">The New York Times</a></i>. For instance, a 2022 article stated that benzene contamination in the <a href="/wiki/Boston_metropolitan_area" class="mw-redirect" title="Boston metropolitan area">Boston metropolitan area</a> caused hazardous conditions in multiple places, with the publication noting that the compound may eventually cause <a href="/wiki/Leukemia" title="Leukemia">leukemia</a> in some individuals.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Discovery">Discovery</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=2" title="Edit section: Discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word "<i>benzene</i>" derives from "<i>gum benzoin</i>" (<a href="/wiki/Benzoin_(resin)" title="Benzoin (resin)">benzoin resin</a>), an aromatic resin known since ancient times in Southeast Asia, and later to European pharmacists and perfumers in the 16th century via trade routes.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> An <a href="/wiki/Acid" title="Acid">acidic</a> material was derived from benzoin by <a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">sublimation</a>, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.<sup id="cite_ref-rocke_17-0" class="reference"><a href="#cite_note-rocke-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Michael_Faraday" title="Michael Faraday">Michael Faraday</a> first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name <i>bicarburet of hydrogen</i>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> In 1833, <a href="/wiki/Eilhard_Mitscherlich" title="Eilhard Mitscherlich">Eilhard Mitscherlich</a> produced it by <a href="/wiki/Distillation" title="Distillation">distilling</a> <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> (from <a href="/wiki/Benzoin_(resin)" title="Benzoin (resin)">gum benzoin</a>) and <a href="/wiki/Calcium_oxide" title="Calcium oxide">lime</a>. He gave the compound the name <i>benzin</i>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> In 1836, the French chemist <a href="/wiki/Auguste_Laurent" title="Auguste Laurent">Auguste Laurent</a> named the substance "phène";<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> this word has become the root of the English word "<a href="/wiki/Phenol" title="Phenol">phenol</a>", which is <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> benzene, and "<a href="/wiki/Phenyl_group" title="Phenyl group">phenyl</a>", the radical formed by abstraction of a hydrogen atom from benzene. </p><p>In 1845, <a href="/wiki/Charles_Blachford_Mansfield" title="Charles Blachford Mansfield">Charles Blachford Mansfield</a>, working under <a href="/wiki/August_Wilhelm_von_Hofmann" title="August Wilhelm von Hofmann">August Wilhelm von Hofmann</a>, isolated benzene from <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Four years later, Mansfield began the first industrial-scale production of benzene, based on the coal-tar method.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Gradually, the sense developed among chemists that a number of substances were chemically related to benzene, comprising a diverse chemical family. In 1855, Hofmann was the first to apply the word "<a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a>" to designate this family relationship, after a characteristic property of many of its members.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In 1997, benzene was <a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">detected in deep space</a>.<sup id="cite_ref-Cernicharo_546_26-0" class="reference"><a href="#cite_note-Cernicharo_546-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ring_formula">Ring formula</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=3" title="Edit section: Ring formula"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" style="text-align:center; font-size:90%; margin-left:20px;" width="50%"> <tbody><tr> <th colspan="6">Historic proposals of benzene structures </th></tr> <tr style="background-color:white"> <td><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formula_Claus_1867_(original)2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/120px-Historic_Benzene_Formula_Claus_1867_%28original%292.png" decoding="async" width="120" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/180px-Historic_Benzene_Formula_Claus_1867_%28original%292.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formula_Claus_1867_%28original%292.png/240px-Historic_Benzene_Formula_Claus_1867_%28original%292.png 2x" data-file-width="334" data-file-height="367" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formula_Dewar_1869_(original_Dewar_benzene).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/91px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png" decoding="async" width="91" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/137px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png/182px-Historic_Benzene_Formula_Dewar_1869_%28original_Dewar_benzene%29.png 2x" data-file-width="348" data-file-height="459" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formula_Ladenburg_1869_(original).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png/120px-Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png" decoding="async" width="80" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png/160px-Historic_Benzene_Formula_Ladenburg_1869_%28original%29.png 2x" data-file-width="233" data-file-height="290" /></a></span> </td></tr> <tr align="center" style="vertical-align:top"> <td>By <a href="/wiki/Adolf_Karl_Ludwig_Claus" title="Adolf Karl Ludwig Claus">Adolf Karl Ludwig Claus</a> (1867)<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </td> <td>Listed, but not supported,<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup> by <a href="/wiki/James_Dewar" title="James Dewar">James Dewar</a> (1869)<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </td> <td>By <a href="/wiki/Albert_Ladenburg" title="Albert Ladenburg">Albert Ladenburg</a> (1869)<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="3" style="background:#FFFFFF"><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formulae_Kekul%C3%A9_(original).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/300px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png" decoding="async" width="300" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/450px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/600px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 2x" data-file-width="1081" data-file-height="375" /></a></span> </td></tr> <tr align="center" style="vertical-align:top"> <td colspan="3">By <a href="/wiki/August_Kekul%C3%A9" title="August Kekulé">August Kekulé</a> (1865/1872)<sup id="cite_ref-Kekulé1865_31-0" class="reference"><a href="#cite_note-Kekulé1865-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </td></tr> <tr style="background-color:white"> <td><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formulae_Armstrong_(original).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/130px-Historic_Benzene_Formulae_Armstrong_%28original%29.png" decoding="async" width="130" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/195px-Historic_Benzene_Formulae_Armstrong_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Historic_Benzene_Formulae_Armstrong_%28original%29.png/260px-Historic_Benzene_Formulae_Armstrong_%28original%29.png 2x" data-file-width="504" data-file-height="453" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formula_Baeyer_1888_(original).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/150px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png" decoding="async" width="150" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/225px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Historic_Benzene_Formula_Baeyer_1888_%28original%29.png/300px-Historic_Benzene_Formula_Baeyer_1888_%28original%29.png 2x" data-file-width="444" data-file-height="381" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formula_Thiele_1899_(original).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/90px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png" decoding="async" width="90" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/135px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Historic_Benzene_Formula_Thiele_1899_%28original%29.png/180px-Historic_Benzene_Formula_Thiele_1899_%28original%29.png 2x" data-file-width="201" data-file-height="352" /></a></span> </td></tr> <tr align="center" style="vertical-align:top"> <td>By <a href="/wiki/Henry_Edward_Armstrong" title="Henry Edward Armstrong">Henry Edward Armstrong</a> (1887)<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </td> <td>By <a href="/wiki/Adolf_von_Baeyer" title="Adolf von Baeyer">Adolf von Baeyer</a> (1888)<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </td> <td>By <a href="/wiki/Johannes_Thiele_(chemist)" title="Johannes Thiele (chemist)">Friedrich Karl Johannes Thiele</a> (1899)<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>The <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> for benzene was long known, but its highly <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">polyunsaturated</a> structure, with just one <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom for each <a href="/wiki/Carbon" title="Carbon">carbon</a> atom, was challenging to determine. <a href="/wiki/Archibald_Scott_Couper" title="Archibald Scott Couper">Archibald Scott Couper</a> in 1858 and <a href="/wiki/Johann_Josef_Loschmidt" title="Johann Josef Loschmidt">Johann Josef Loschmidt</a> in 1861<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> suggested possible structures that contained multiple double bonds or multiple rings, but in these years very little was known about aromatic chemistry, and so chemists were unable to adduce appropriate evidence to favor any particular formula. </p><p>But many chemists had begun to work on aromatic substances, especially in Germany, and relevant data was coming fast. In 1865, the German chemist <a href="/wiki/Friedrich_August_Kekul%C3%A9" class="mw-redirect" title="Friedrich August Kekulé">Friedrich August Kekulé</a> published a paper in French (for he was then teaching in Francophone Belgium) suggesting that the structure contained a ring of six carbon atoms with alternating single and double bonds. The next year he published a much longer paper in German on the same subject.<sup id="cite_ref-Kekulé1865_31-1" class="reference"><a href="#cite_note-Kekulé1865-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Kekulé used evidence that had accumulated in the intervening years—namely, that there always appeared to be only one <a href="/wiki/Isomer" title="Isomer">isomer</a> of any <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">monoderivative</a> of benzene, and that there always appeared to be exactly three isomers of every disubstituted derivative—now understood to correspond to the ortho, meta, and para patterns of <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">arene substitution</a>—to argue in support of his proposed structure.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 carbon-hydrogen ratio. </p> <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 348px"> <div class="thumb" style="width: 346px;"><span typeof="mw:File"><a href="/wiki/File:Historic_Benzene_Formulae_Kekul%C3%A9_(original).png" class="mw-file-description" title="Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds[note 2]"><img alt="Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds[note 2]" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/519px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png" decoding="async" width="346" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/779px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png/1038px-Historic_Benzene_Formulae_Kekul%C3%A9_%28original%29.png 2x" data-file-width="1081" data-file-height="375" /></a></span></div> <div class="gallerytext">Kekulé's 1872 modification of his 1865 theory, illustrating rapid alternation of double bonds<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>note 2<span class="cite-bracket">]</span></a></sup></div> </li> </ul> <p>The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry that in 1890 the <a href="/wiki/German_Chemical_Society" title="German Chemical Society">German Chemical Society</a> organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake biting its own tail (a symbol in ancient cultures known as the <a href="/wiki/Ouroboros" title="Ouroboros">ouroboros</a>).<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> This vision, he said, came to him after years of studying the nature of carbon-carbon bonds. This was seven years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. Curiously, a similar, humorous depiction of benzene had appeared in 1886 in a pamphlet entitled <i>Berichte der Durstigen Chemischen Gesellschaft</i> (Journal of the Thirsty Chemical Society), a parody of the <i>Berichte der Deutschen Chemischen Gesellschaft</i>, only the parody had monkeys seizing each other in a circle, rather than snakes as in Kekulé's anecdote.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well known through oral transmission even if it had not yet appeared in print.<sup id="cite_ref-rocke_17-1" class="reference"><a href="#cite_note-rocke-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Kekulé's 1890 speech<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> in which this anecdote appeared has been translated into English.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> If the anecdote is the memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>In 1929, the cyclic nature of benzene was finally confirmed by the <a href="/wiki/Crystallography" title="Crystallography">crystallographer</a> <a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Kathleen Lonsdale</a> using <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> methods.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Using large crystals of <a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">hexamethylbenzene</a>, a benzene derivative with the same core of six carbon atoms, Lonsdale obtained diffraction patterns. Through calculating more than thirty parameters, Lonsdale demonstrated that the benzene ring could not be anything but a flat hexagon, and provided accurate distances for all carbon-carbon bonds in the molecule.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Nomenclature">Nomenclature</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=4" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The German chemist <a href="/wiki/Wilhelm_K%C3%B6rner" title="Wilhelm Körner">Wilhelm Körner</a> suggested the prefixes ortho-, meta-, para- to distinguish di-substituted benzene derivatives in 1867; however, he did not use the prefixes to distinguish the relative positions of the substituents on a benzene ring.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> It was the German chemist <a href="/wiki/Carl_Gr%C3%A4be" class="mw-redirect" title="Carl Gräbe">Carl Gräbe</a> who, in 1869, first used the prefixes ortho-, meta-, para- to denote specific relative locations of the substituents on a di-substituted aromatic ring (viz, naphthalene).<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> In 1870, the German chemist <a href="/wiki/Viktor_Meyer" title="Viktor Meyer">Viktor Meyer</a> first applied Gräbe's nomenclature to benzene.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Early_applications">Early applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=5" title="Edit section: Early applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1903, <a href="/wiki/Ludwig_Roselius" title="Ludwig Roselius">Ludwig Roselius</a> popularized the use of benzene to <a href="/wiki/Decaffeination" title="Decaffeination">decaffeinate</a> <a href="/wiki/Coffee" title="Coffee">coffee</a>. This discovery led to the production of <a href="/wiki/Sanka" title="Sanka">Sanka</a>. This process was later discontinued. Benzene was historically used as a significant component in many consumer products such as <a href="/wiki/Penetrating_oil" title="Penetrating oil">liquid wrench</a>, several <a href="/wiki/Paint_stripper" title="Paint stripper">paint strippers</a>, <a href="/wiki/Rubber_cement" title="Rubber cement">rubber cements</a>, spot removers, and other products. Manufacture of some of these benzene-containing formulations ceased in about 1950, although Liquid Wrench continued to contain significant amounts of benzene until the late 1970s.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Occurrence">Occurrence</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=6" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Trace amounts of benzene are found in petroleum and coal. It is a byproduct of the incomplete combustion of many materials. For commercial use, until <a href="/wiki/World_War_II" title="World War II">World War II</a>, much of benzene was obtained as a by-product of <a href="/wiki/Coke_(fuel)" title="Coke (fuel)">coke</a> production (or "coke-oven light oil") for the <a href="/wiki/Steel" title="Steel">steel</a> industry. However, in the 1950s, increased demand for benzene, especially from the growing <a href="/wiki/Polymer" title="Polymer">polymers</a> industry, necessitated the production of benzene from petroleum. Today, most benzene comes from the <a href="/wiki/Petrochemical_industry" title="Petrochemical industry">petrochemical industry</a>, with only a small fraction being produced from coal.<sup id="cite_ref-Ullmann_54-0" class="reference"><a href="#cite_note-Ullmann-54"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Benzene has been detected on <a href="/wiki/Mars" title="Mars">Mars</a>.<sup id="cite_ref-NYT-20180607_55-0" class="reference"><a href="#cite_note-NYT-20180607-55"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SCI-20180608a_56-0" class="reference"><a href="#cite_note-SCI-20180608a-56"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SCI-20180608c_57-0" class="reference"><a href="#cite_note-SCI-20180608c-57"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=7" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Benzene_Representations.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/400px-Benzene_Representations.svg.png" decoding="async" width="400" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/600px-Benzene_Representations.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Benzene_Representations.svg/800px-Benzene_Representations.svg.png 2x" data-file-width="1600" data-file-height="900" /></a><figcaption>The various representations of benzene.</figcaption></figure> <p><a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> shows that all six carbon-carbon bonds in benzene are of the same length, at 140 <a href="/wiki/Picometre" title="Picometre">picometres</a> (pm).<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> The C–C <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> are greater than a double bond (135 pm) but shorter than a single bond (147 pm). This intermediate distance is caused by electron <a href="/wiki/Delocalized_electron" title="Delocalized electron">delocalization</a>: the electrons for C=C bonding are distributed equally between each of the six carbon atoms. Benzene has 6 hydrogen atoms, fewer than the corresponding parent <a href="/wiki/Alkane" title="Alkane">alkane</a>, <a href="/wiki/Hexane" title="Hexane">hexane</a>, which has 14. Benzene and <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> have a similar structure, only the ring of delocalized electrons and the loss of one hydrogen per carbon distinguishes it from cyclohexane. The molecule is planar.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> The molecular orbital description involves the formation of three delocalized <a href="/wiki/Pi_bond" title="Pi bond">π orbitals</a> spanning all six carbon atoms, while the valence bond description involves a superposition of <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance structures</a>.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> It is likely that this stability contributes to the peculiar molecular and chemical properties known as <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>. To reflect the delocalized nature of the bonding, benzene is often depicted with a circle inside a hexagonal arrangement of carbon atoms. </p><p>Derivatives of benzene occur sufficiently often as a component of organic molecules, so much so that the <a href="/wiki/Unicode" title="Unicode">Unicode</a> Consortium has allocated a symbol in the <a href="/wiki/Miscellaneous_Technical_(Unicode)" class="mw-redirect" title="Miscellaneous Technical (Unicode)">Miscellaneous Technical</a> block with the code U+232C (⌬) to represent it with three double bonds,<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> and U+23E3 (⏣) for a delocalized version.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Benzene_derivatives">Benzene derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=8" title="Edit section: Benzene derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Aromatic_hydrocarbons" class="mw-redirect" title="Aromatic hydrocarbons">Aromatic hydrocarbons</a> and <a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></div> <p>Many important chemical compounds are derived from benzene by replacing one or more of its hydrogen atoms with another <a href="/wiki/Functional_group" title="Functional group">functional group</a>. Examples of simple benzene derivatives are <a href="/wiki/Phenol" title="Phenol">phenol</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, and <a href="/wiki/Aniline" title="Aniline">aniline</a>, abbreviated PhOH, PhMe, and PhNH<sub>2</sub>, respectively. Linking benzene rings gives <a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a>, C<sub>6</sub>H<sub>5</sub>–C<sub>6</sub>H<sub>5</sub>. Further loss of hydrogen gives "fused" aromatic hydrocarbons, such as <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>, <a href="/wiki/Anthracene" title="Anthracene">anthracene</a>, <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a>, and <a href="/wiki/Pyrene" title="Pyrene">pyrene</a>. The limit of the fusion process is the hydrogen-free allotrope of carbon, <a href="/wiki/Graphite" title="Graphite">graphite</a>. </p><p>In <a href="/wiki/Heterocyclic_chemistry" class="mw-redirect" title="Heterocyclic chemistry">heterocycles</a>, carbon atoms in the benzene ring are replaced with other elements. The most important variations contain <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>. Replacing one CH with N gives the compound <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, C<sub>5</sub>H<sub>5</sub>N. Although benzene and pyridine are <i>structurally</i> related, benzene cannot be converted into pyridine. Replacement of a second CH bond with N gives, depending on the location of the second N, <a href="/wiki/Pyridazine" title="Pyridazine">pyridazine</a>, <a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidine</a>, or <a href="/wiki/Pyrazine" title="Pyrazine">pyrazine</a>.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=9" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Four chemical processes contribute to industrial benzene production: <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">catalytic reforming</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a> hydrodealkylation, toluene disproportionation, and <a href="/wiki/Steam_cracking" title="Steam cracking">steam cracking</a> etc. According to the <a href="/wiki/ATSDR" class="mw-redirect" title="ATSDR">ATSDR</a> Toxicological Profile for benzene, between 1978 and 1981, catalytic reformates accounted for approximately 44–50% of the total U.S. benzene production.<sup id="cite_ref-Ullmann_54-1" class="reference"><a href="#cite_note-Ullmann-54"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Catalytic_reforming">Catalytic reforming</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=10" title="Edit section: Catalytic reforming"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In catalytic reforming, a mixture of <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> with boiling points between 60 and 200 °C is blended with <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> gas and then exposed to a <a href="/wiki/Bifunctional" class="mw-redirect" title="Bifunctional">bifunctional</a> <a href="/wiki/Platinum(II)_chloride" title="Platinum(II) chloride">platinum chloride</a> or <a href="/wiki/Rhenium" title="Rhenium">rhenium</a> chloride <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> at 500–525 °C and pressures ranging from 8–50 atm. Under these conditions, <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by <a href="/wiki/Liquid-liquid_extraction" class="mw-redirect" title="Liquid-liquid extraction">extraction</a> with any one of a number of <a href="/wiki/Solvent" title="Solvent">solvents</a>, including <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a> or <a href="/wiki/Sulfolane" title="Sulfolane">sulfolane</a>, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce aromatics with lowest non-aromatic components. Recovery of the aromatics, commonly referred to as <a href="/wiki/BTX_(chemistry)" title="BTX (chemistry)">BTX</a> (benzene, toluene and xylene isomers), involves such extraction and distillation steps. </p><p>In similar fashion to this catalytic reforming, <a href="/wiki/UOP_LLC" class="mw-redirect" title="UOP LLC">UOP</a> and <a href="/wiki/BP" title="BP">BP</a> commercialized a method from LPG (mainly propane and butane) to aromatics. </p> <div class="mw-heading mw-heading3"><h3 id="Toluene_hydrodealkylation">Toluene hydrodealkylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=11" title="Edit section: Toluene hydrodealkylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Toluene <a href="/wiki/Hydrodealkylation" title="Hydrodealkylation">hydrodealkylation</a> converts <a href="/wiki/Toluene" title="Toluene">toluene</a> to benzene. In this hydrogen-intensive process, toluene is mixed with hydrogen, then passed over a <a href="/wiki/Chromium" title="Chromium">chromium</a>, <a href="/wiki/Molybdenum" title="Molybdenum">molybdenum</a>, or <a href="/wiki/Platinum" title="Platinum">platinum</a> <a href="/wiki/Oxide" title="Oxide">oxide</a> catalyst at 500–650 °C and 20–60 atm pressure. Sometimes, higher temperatures are used instead of a catalyst (at the similar reaction condition). Under these conditions, toluene undergoes dealkylation to benzene and <a href="/wiki/Methane" title="Methane">methane</a>: </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">3</sub> + H<sub class="template-chem2-sub">2</sub> → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub> + CH<sub class="template-chem2-sub">4</sub></span></dd></dl> <p>This irreversible reaction is accompanied by an equilibrium side reaction that produces <a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a> (diphenyl) at higher temperature: </p> <dl><dd>2 <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span></span> ⇌ <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> + <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span>–C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></span></dd></dl> <p>If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen. </p><p>A typical reaction yield exceeds 95%. Sometimes, <a href="/wiki/Xylene" title="Xylene">xylenes</a> and heavier aromatics are used in place of toluene, with similar efficiency. </p><p>This is often called "on-purpose" methodology to produce benzene, compared to conventional BTX (benzene-toluene-xylene) extraction processes. </p> <div class="mw-heading mw-heading3"><h3 id="Toluene_disproportionation">Toluene disproportionation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=12" title="Edit section: Toluene disproportionation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Toluene <a href="/wiki/Disproportionation" title="Disproportionation">disproportionation</a> (<b>TDP</b>) is the conversion of toluene to benzene and <a href="/wiki/Xylene" title="Xylene">xylene</a>.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>Given that demand for <i>para</i>-xylene (<a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-xylene</a>) substantially exceeds demand for other xylene isomers, a refinement of the TDP process called <b>Selective TDP</b> (STDP) may be used. In this process, the xylene stream exiting the TDP unit is approximately 90% <i>p</i>-xylene. In some systems, even the benzene-to-xylenes ratio is modified to favor xylenes. </p> <div class="mw-heading mw-heading3"><h3 id="Steam_cracking">Steam cracking</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=13" title="Edit section: Steam cracking"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Steam_cracking" title="Steam cracking">Steam cracking</a> is the process for producing <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and other <a href="/wiki/Alkene" title="Alkene">alkenes</a> from <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic hydrocarbons</a>. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid by-product called <i><a href="/wiki/Pyrolysis_gasoline" title="Pyrolysis gasoline">pyrolysis gasoline</a></i>. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or routed through an extraction process to recover <a href="/wiki/BTX_(chemistry)" title="BTX (chemistry)">BTX</a> aromatics (benzene, toluene and xylenes). </p> <div class="mw-heading mw-heading3"><h3 id="Other_methods">Other methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=14" title="Edit section: Other methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although of no commercial significance, many other routes to benzene exist. <a href="/wiki/Phenol" title="Phenol">Phenol</a> and <a href="/wiki/Halobenzene" title="Halobenzene">halobenzenes</a> can be reduced with metals. <a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a> and its salts undergo <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> to benzene. The reaction of the <a href="/wiki/Diazonium_compound" title="Diazonium compound">diazonium compound</a> derived from <a href="/wiki/Aniline" title="Aniline">aniline</a> with <a href="/wiki/Hypophosphorus_acid" class="mw-redirect" title="Hypophosphorus acid">hypophosphorus acid</a> gives benzene. <a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a> of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> gives benzene. Complete <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Mellitic_acid" title="Mellitic acid">mellitic acid</a> gives benzene. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=15" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzene is used mainly as an intermediate to make other chemicals, above all <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a> (and other <a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">alkylbenzenes</a>), <a href="/wiki/Cumene" title="Cumene">cumene</a>, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>, and <a href="/wiki/Nitrobenzene" title="Nitrobenzene">nitrobenzene</a>. In 1988 it was reported that two-thirds of all chemicals on the <a href="/wiki/American_Chemical_Society" title="American Chemical Society">American Chemical Society</a>'s lists contained at least one benzene ring.<sup id="cite_ref-nyt_68-0" class="reference"><a href="#cite_note-nyt-68"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> More than half of the entire benzene production is processed into ethylbenzene, a precursor to <a href="/wiki/Styrene" title="Styrene">styrene</a>, which is used to make polymers and plastics like <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>. Some 20% of the benzene production is used to manufacture cumene, which is needed to produce <a href="/wiki/Phenol" title="Phenol">phenol</a> and acetone for resins and adhesives. <a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a> consumes around 10% of the world's benzene production; it is primarily used in the manufacture of nylon fibers, which are processed into textiles and engineering plastics. Smaller amounts of benzene are used to make some types of <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubbers</a>, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, <a href="/wiki/Dye" title="Dye">dyes</a>, <a href="/wiki/Detergent" title="Detergent">detergents</a>, <a href="/wiki/Drug" title="Drug">drugs</a>, <a href="/wiki/Explosive" title="Explosive">explosives</a>, and <a href="/wiki/Pesticide" title="Pesticide">pesticides</a>. In 2013, the biggest consumer country of benzene was China, followed by the USA. Benzene production is currently expanding in the Middle East and in Africa, whereas production capacities in Western Europe and North America are stagnating.<sup id="cite_ref-Ceresana_69-0" class="reference"><a href="#cite_note-Ceresana-69"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Toluene" title="Toluene">Toluene</a> is now often used as a substitute for benzene, for instance as a fuel additive. The solvent-properties of the two are similar, but toluene is less toxic and has a wider liquid range. Toluene is also processed into benzene.<sup id="cite_ref-CeresanaB_70-0" class="reference"><a href="#cite_note-CeresanaB-70"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center noresize" typeof="mw:File/Thumb"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Benzene_uses.png/960px-Benzene_uses.png" decoding="async" width="600" height="374" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Benzene_uses.png/1200px-Benzene_uses.png 2x" data-file-width="2788" data-file-height="1737" usemap="#ImageMap_ef38bf12dc61fe65" resource="/wiki/File:Benzene_uses.png" /></span><map name="ImageMap_ef38bf12dc61fe65"><area href="#Uses" shape="rect" coords="8,142,94,174" alt="Benzene" title="Benzene" /><area href="/wiki/Ethylbenzene" shape="rect" coords="143,13,229,45" alt="Ethylbenzene" title="Ethylbenzene" /><area href="/wiki/Cumene" shape="rect" coords="143,92,229,125" alt="Cumene" title="Cumene" /><area href="/wiki/Cyclohexane" shape="rect" coords="143,171,229,203" alt="Cyclohexane" title="Cyclohexane" /><area href="/wiki/Aniline" shape="rect" coords="143,250,229,283" alt="Aniline" title="Aniline" /><area href="/wiki/Chlorobenzene" shape="rect" coords="143,330,229,363" alt="Chlorobenzene" title="Chlorobenzene" /><area href="/wiki/Acetone" shape="rect" coords="262,74,347,107" alt="Acetone" title="Acetone" /><area href="/wiki/Phenol" shape="rect" coords="262,137,347,169" alt="Phenol" title="Phenol" /><area href="/wiki/Styrene" shape="rect" coords="380,12,466,45" alt="Styrene" title="Styrene" /><area href="/wiki/Bisphenol_A" shape="rect" coords="380,93,466,126" alt="Bisphenol A" title="Bisphenol A" /><area href="/wiki/Adipic_acid" shape="rect" coords="380,233,466,265" alt="Adipic acid" title="Adipic acid" /><area href="/wiki/Caprolactam" shape="rect" coords="380,287,466,319" alt="Caprolactam" title="Caprolactam" /><area href="/wiki/Polystyrene" shape="rect" coords="498,12,584,45" alt="Polystyrene" title="Polystyrene" /><area href="/wiki/Polycarbonate" shape="rect" coords="498,68,584,99" alt="Polycarbonate" title="Polycarbonate" /><area href="/wiki/Epoxy_resin" shape="rect" coords="498,123,584,154" alt="Epoxy resin" title="Epoxy resin" /><area href="/wiki/Phenolic_resin" shape="rect" coords="498,177,584,210" alt="Phenolic resin" title="Phenolic resin" /><area href="/wiki/Nylon_6-6" shape="rect" coords="498,233,584,265" alt="Nylon 6-6" title="Nylon 6-6" /><area href="/wiki/Nylon_6" shape="rect" coords="498,287,584,320" alt="Nylon 6" title="Nylon 6" /></map><figcaption>Major commodity chemicals and polymers derived from benzene. Clicking on the image loads the appropriate article</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Component_of_gasoline">Component of gasoline</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=16" title="Edit section: Component of gasoline"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> (petrol) additive, benzene increases the <a href="/wiki/Octane_rating" title="Octane rating">octane rating</a> and reduces <a href="/wiki/Engine_knocking" title="Engine knocking">knocking</a>. As a consequence, gasoline often contained several percent benzene before the 1950s, when <a href="/wiki/Tetraethyl_lead" class="mw-redirect" title="Tetraethyl lead">tetraethyl lead</a> replaced it as the most widely used antiknock additive. With the global phaseout of leaded gasoline, benzene has made a comeback as a gasoline additive in some nations. In the <a href="/wiki/United_States" title="United States">United States</a>, concern over its negative health effects and the possibility of benzene entering the <a href="/wiki/Groundwater" title="Groundwater">groundwater</a> has led to stringent regulation of gasoline's benzene content, with limits typically around 1%.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> European petrol specifications now contain the same 1% limit on benzene content. The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> introduced new regulations in 2011 that lowered the benzene content in gasoline to 0.62%.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p><p>In some European languages, the word for petroleum or gasoline is an exact cognate of "benzene". For instance in <a href="/wiki/Catalan_language" title="Catalan language">Catalan</a> the word 'benzina' can be used for gasoline, though now it is relatively rare. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=17" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most common reactions of benzene involve substitution of a proton by other groups.<sup id="cite_ref-StranksEtAl1970_73-0" class="reference"><a href="#cite_note-StranksEtAl1970-73"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">Electrophilic aromatic substitution</a> is a general method of derivatizing benzene. Benzene is sufficiently <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilic</a> that it undergoes substitution by <a href="/wiki/Acylium" class="mw-redirect" title="Acylium">acylium</a> ions and alkyl <a href="/wiki/Carbocation" title="Carbocation">carbocations</a> to give substituted derivatives. </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:OChem-Mech-ElectrophilicAromaticSubstitution-General.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png/450px-OChem-Mech-ElectrophilicAromaticSubstitution-General.png" decoding="async" width="450" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png/675px-OChem-Mech-ElectrophilicAromaticSubstitution-General.png 1.5x, //upload.wikimedia.org/wikipedia/commons/5/57/OChem-Mech-ElectrophilicAromaticSubstitution-General.png 2x" data-file-width="712" data-file-height="118" /></a><figcaption>Electrophilic aromatic substitution of benzene</figcaption></figure></dd></dl> <p>The most widely practiced example of this reaction is the <a href="/wiki/Ethylation" class="mw-redirect" title="Ethylation">ethylation</a> of benzene. </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:EtC6H5route.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/320px-EtC6H5route.png" decoding="async" width="320" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/480px-EtC6H5route.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/EtC6H5route.png/640px-EtC6H5route.png 2x" data-file-width="1453" data-file-height="297" /></a></span></dd></dl></dd></dl> <p>Approximately 24,700,000 tons were produced in 1999.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> Highly instructive but of far less industrial significance is the <a href="/wiki/Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a> of benzene (and many other aromatic rings) using an <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halide</a> in the presence of a strong Lewis acid catalyst. Similarly, the <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylation</a> is a related example of <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a>. The reaction involves the <a href="/wiki/Acylation" title="Acylation">acylation</a> of benzene (or many other aromatic rings) with an <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chloride</a> using a strong <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> such as <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a> or <a href="/wiki/Iron(III)_chloride" title="Iron(III) chloride">Iron(III) chloride</a>. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Benzen_acylowany.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/300px-Benzen_acylowany.svg.png" decoding="async" width="300" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/450px-Benzen_acylowany.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Benzen_acylowany.svg/600px-Benzen_acylowany.svg.png 2x" data-file-width="3371" data-file-height="869" /></a><figcaption>Friedel-Crafts acylation of benzene by acetyl chloride</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Sulfonation,_chlorination,_nitration"><span id="Sulfonation.2C_chlorination.2C_nitration"></span>Sulfonation, chlorination, nitration</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=18" title="Edit section: Sulfonation, chlorination, nitration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Using electrophilic aromatic substitution, many functional groups are introduced onto the benzene framework. <a href="/wiki/Aromatic_sulfonation" title="Aromatic sulfonation">Sulfonation</a> of benzene involves the use of <a href="/wiki/Oleum" title="Oleum">oleum</a>, a mixture of sulfuric acid with <a href="/wiki/Sulfur_trioxide" title="Sulfur trioxide">sulfur trioxide</a>. Sulfonated benzene derivatives are useful <a href="/wiki/Detergent" title="Detergent">detergents</a>. In <a href="/wiki/Nitration" title="Nitration">nitration</a>, benzene reacts with nitronium ions (NO<sub>2</sub><sup>+</sup>), which is a strong electrophile produced by combining sulfuric and nitric acids. <a href="/wiki/Nitrobenzene" title="Nitrobenzene">Nitrobenzene</a> is the precursor to <a href="/wiki/Aniline" title="Aniline">aniline</a>. Chlorination is achieved with chlorine to give <a href="/wiki/Chlorobenzene" title="Chlorobenzene">chlorobenzene</a> in the presence of a Lewis acid catalyst such as aluminium tri-chloride. </p> <div class="mw-heading mw-heading3"><h3 id="Hydrogenation">Hydrogenation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=19" title="Edit section: Hydrogenation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Via <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, benzene and its derivatives convert to <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> and derivatives. This reaction is achieved by the use of high pressures of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> in the presence of <a href="/wiki/Heterogeneous_catalyst" class="mw-redirect" title="Heterogeneous catalyst">heterogeneous catalysts</a>, such as finely divided <a href="/wiki/Nickel" title="Nickel">nickel</a>. Whereas alkenes can be hydrogenated near room temperatures, benzene and related compounds are more reluctant substrates, requiring temperatures >100 °C. This reaction is practiced on a large scale industrially. In the absence of the catalyst, benzene is impervious to hydrogen. Hydrogenation cannot be stopped to give cyclohexene or cyclohexadienes as these are superior substrates. <a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a>, a non catalytic process, however selectively hydrogenates benzene to the diene. </p> <div class="mw-heading mw-heading3"><h3 id="Metal_complexes">Metal complexes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=20" title="Edit section: Metal complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzene is an excellent <a href="/wiki/Ligand" title="Ligand">ligand</a> in the <a href="/wiki/Complex_(chemistry)" class="mw-redirect" title="Complex (chemistry)">organometallic</a> chemistry of low-valent metals. Important examples include the sandwich and half-sandwich complexes, respectively, <a href="/wiki/Bis(benzene)chromium" title="Bis(benzene)chromium">Cr(C<sub>6</sub>H<sub>6</sub>)<sub>2</sub></a> and <a href="/wiki/(Benzene)ruthenium_dichloride_dimer" title="(Benzene)ruthenium dichloride dimer">[RuCl<sub>2</sub>(C<sub>6</sub>H<sub>6</sub>)]<sub>2</sub></a>. </p> <div class="mw-heading mw-heading2"><h2 id="Health_effects">Health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=21" title="Edit section: Health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Benzol.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Benzol.JPG/220px-Benzol.JPG" decoding="async" width="220" height="308" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Benzol.JPG/330px-Benzol.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/8/8f/Benzol.JPG 2x" data-file-width="414" data-file-height="580" /></a><figcaption>A bottle of benzene. The warnings show benzene is a toxic and flammable liquid.</figcaption></figure> <p>Benzene is classified as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>, which increases the risk of <a href="/wiki/Cancer" title="Cancer">cancer</a> and other illnesses, and is also a notorious cause of <a href="/wiki/Bone_marrow_failure" title="Bone marrow failure">bone marrow failure</a>. Substantial quantities of epidemiologic, clinical, and laboratory data link benzene to aplastic anemia, acute <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>, bone marrow abnormalities and cardiovascular disease.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bard_2014_Jun_16;9(6)_77-0" class="reference"><a href="#cite_note-Bard_2014_Jun_16;9(6)-77"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> The specific hematologic malignancies that benzene is associated with include: acute myeloid leukemia (AML), aplastic anemia, myelodysplastic syndrome (MDS), acute lymphoblastic leukemia (ALL), and chronic myeloid leukemia (CML).<sup id="cite_ref-Smith_2010_133–48_78-0" class="reference"><a href="#cite_note-Smith_2010_133–48-78"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p>Carcinogenic activity of benzene was discovered by Swedish pharmacologist <a href="/w/index.php?title=Carl_Gustaf_Santesson_(farmakolog)&action=edit&redlink=1" class="new" title="Carl Gustaf Santesson (farmakolog) (page does not exist)">C. G. Santesson</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://se.wikipedia.org/wiki/Carl_Gustaf_Santesson" class="extiw" title="se:Carl Gustaf Santesson">se</a>]</span> in 1897 on female workers of a tire-making factory.<sup id="cite_ref-79" class="reference"><a href="#cite_note-79"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/American_Petroleum_Institute" title="American Petroleum Institute">American Petroleum Institute</a> (API) stated in 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero".<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> There is no safe exposure level; even tiny amounts can cause harm.<sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/US_Department_of_Health_and_Human_Services" class="mw-redirect" title="US Department of Health and Human Services">US Department of Health and Human Services</a> (DHHS) classifies benzene as a human carcinogen. Long-term exposure to excessive levels of benzene in the air causes leukemia, a potentially fatal cancer of the blood-forming organs. In particular, <a href="/wiki/Acute_myeloid_leukemia" title="Acute myeloid leukemia">acute myeloid leukemia</a> or <a href="/wiki/Acute_nonlymphocytic_leukemia" class="mw-redirect" title="Acute nonlymphocytic leukemia">acute nonlymphocytic leukemia</a> (AML & ANLL) is caused by benzene.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> IARC rated benzene as "known to be carcinogenic to humans" (<a href="/wiki/IARC_group_1_Carcinogens" class="mw-redirect" title="IARC group 1 Carcinogens">Group 1</a>). </p><p>As benzene is ubiquitous in gasoline and hydrocarbon fuels that are in use everywhere, human exposure to benzene is a global health problem. Benzene targets the liver, kidney, lung, heart and brain and can cause <a href="/wiki/DNA" title="DNA">DNA</a> strand breaks and <a href="/wiki/Chromosomal" class="mw-redirect" title="Chromosomal">chromosomal</a> damage, hence is <a href="/wiki/Teratology#Teratogenesis" title="Teratology">teratogenic</a> and <a href="/wiki/Mutagen" title="Mutagen">mutagenic</a>. Benzene causes cancer in animals including humans. Benzene has been shown to cause cancer in both sexes of multiple species of laboratory animals exposed via various routes.<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Exposure_to_benzene">Exposure to benzene</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=22" title="Edit section: Exposure to benzene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to the <a href="/wiki/Agency_for_Toxic_Substances_and_Disease_Registry" title="Agency for Toxic Substances and Disease Registry">Agency for Toxic Substances and Disease Registry</a> (ATSDR) (2007), benzene is both a synthetically made and naturally occurring chemical from processes that include: volcanic eruptions, wild fires, synthesis of chemicals such as <a href="/wiki/Phenol" title="Phenol">phenol</a>, production of <a href="/wiki/Synthetic_fiber" title="Synthetic fiber">synthetic fibers</a>, and fabrication of <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubbers</a>, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, <a href="/wiki/Pesticide" title="Pesticide">pesticides</a>, medications, and <a href="/wiki/Dye" title="Dye">dyes</a>. The major sources of benzene exposure are <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> smoke, automobile service stations, exhaust from motor vehicles, and industrial emissions; however, ingestion and dermal absorption of benzene can also occur through contact with contaminated water. Benzene is hepatically metabolized and excreted in the <a href="/wiki/Urine" title="Urine">urine</a>. Measurement of air and water levels of benzene is accomplished through collection via <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">activated charcoal</a> tubes, which are then analyzed with a <a href="/wiki/Gas_chromatograph" class="mw-redirect" title="Gas chromatograph">gas chromatograph</a>. The measurement of benzene in humans can be accomplished via <a href="/wiki/Urine_test" title="Urine test">urine</a>, <a href="/wiki/Blood_test" title="Blood test">blood</a>, and <a href="/wiki/Breath_test" title="Breath test">breath tests</a>; however, all of these have their limitations because benzene is rapidly metabolized in the human body.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> </p><p>Exposure to benzene may lead progressively to aplastic <a href="/wiki/Anemia" title="Anemia">anemia</a>, <a href="/wiki/Leukaemia" class="mw-redirect" title="Leukaemia">leukaemia</a>, and <a href="/wiki/Multiple_myeloma" title="Multiple myeloma">multiple myeloma</a>.<sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">OSHA</a> regulates levels of benzene in the workplace.<sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is 1 ppm. As benzene can cause <a href="/wiki/Cancer" title="Cancer">cancer</a>, <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> recommends that all workers wear special <a href="/wiki/Self-contained_breathing_apparatus" title="Self-contained breathing apparatus">breathing equipment</a> when they are likely to be exposed to benzene at levels exceeding the recommended (8-hour) exposure limit of 0.1 ppm.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Benzene_exposure_limits">Benzene exposure limits</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=23" title="Edit section: Benzene exposure limits"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> has set a <a href="/wiki/Maximum_contaminant_level" title="Maximum contaminant level">maximum contaminant level</a> for benzene in <a href="/wiki/Drinking_water" title="Drinking water">drinking water</a> at 0.005 mg/L (5 ppb), as promulgated via the U.S. National Primary Drinking Water Regulations.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> This regulation is based on preventing benzene <a href="/wiki/Leukemogenesis" class="mw-redirect" title="Leukemogenesis">leukemogenesis</a>. The maximum contaminant level goal (<a href="/w/index.php?title=MCLG&action=edit&redlink=1" class="new" title="MCLG (page does not exist)">MCLG</a>), a nonenforceable health goal that would allow an adequate margin of safety for the prevention of adverse effects, is zero benzene concentration in drinking water. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or more of benzene be reported. </p><p>The U.S. <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">Occupational Safety and Health Administration</a> (OSHA) has set a permissible exposure limit of 1 part of benzene per million parts of air (1 ppm) in the workplace during an 8-hour workday, 40-hour workweek. The short term exposure limit for airborne benzene is 5 ppm for 15 minutes.<sup id="cite_ref-OSHASampling2015_91-0" class="reference"><a href="#cite_note-OSHASampling2015-91"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> These legal limits were based on studies demonstrating compelling evidence of health risk to workers exposed to benzene. The risk from exposure to 1 ppm for a working lifetime has been estimated as 5 excess leukemia deaths per 1,000 employees exposed. (This estimate assumes no threshold for benzene's carcinogenic effects.) OSHA has also established an action level of 0.5 ppm to encourage even lower exposures in the workplace.<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </p><p>The U.S. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH) revised the <a href="/wiki/Immediately_Dangerous_to_Life_and_Health" class="mw-redirect" title="Immediately Dangerous to Life and Health">Immediately Dangerous to Life and Health</a> (IDLH) concentration for benzene to 500 ppm. The current NIOSH definition for an IDLH condition, as given in the NIOSH Respirator Selection Logic, is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health effects or prevent escape from such an environment.<sup id="cite_ref-NIOSH2004_93-0" class="reference"><a href="#cite_note-NIOSH2004-93"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> The purpose of establishing an IDLH value is (1) to ensure that the worker can escape from a given contaminated environment in the event of failure of the respiratory protection equipment and (2) is considered a maximum level above which only a highly reliable <a href="/wiki/Self-contained_breathing_apparatus" title="Self-contained breathing apparatus">breathing apparatus</a> providing maximum worker protection is permitted.<sup id="cite_ref-NIOSH2004_93-1" class="reference"><a href="#cite_note-NIOSH2004-93"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> In September 1995, NIOSH issued a new policy for developing <a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">recommended exposure limits</a> (RELs) for substances, including carcinogens. As benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the REL (10-hour) of 0.1 ppm.<sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> The NIOSH short-term exposure limit (STEL – 15 min) is 1 ppm. </p><p>American Conference of Governmental Industrial Hygienists (ACGIH) adopted Threshold Limit Values (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.<sup id="cite_ref-OSHASampling2015_91-1" class="reference"><a href="#cite_note-OSHASampling2015-91"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicology">Toxicology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=24" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Biomarkers_of_exposure">Biomarkers of exposure</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=25" title="Edit section: Biomarkers of exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several tests can determine exposure to benzene. Benzene itself can be measured in breath, blood or urine, but such testing is usually limited to the first 24 hours post-exposure due to the relatively rapid removal of the chemical by exhalation or biotransformation. Most people in developed countries have measureable baseline levels of benzene and other aromatic petroleum hydrocarbons in their blood. In the body, benzene is enzymatically converted to a series of oxidation products including <a href="/wiki/Muconic_acid" title="Muconic acid">muconic acid</a>, <a href="/w/index.php?title=Phenylmercapturic_acid&action=edit&redlink=1" class="new" title="Phenylmercapturic acid (page does not exist)">phenylmercapturic acid</a>, <a href="/wiki/Phenol" title="Phenol">phenol</a>, <a href="/wiki/Catechol" title="Catechol">catechol</a>, <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a> and <a href="/wiki/Hydroxyquinol" title="Hydroxyquinol">1,2,4-trihydroxybenzene</a>. Most of these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of exposure, and they may still be present for some days after exposure has ceased. The current ACGIH biological exposure limits for occupational exposure are 500 μg/g creatinine for muconic acid and 25 μg/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.<sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-99" class="reference"><a href="#cite_note-99"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Biotransformations">Biotransformations</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=26" title="Edit section: Biotransformations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Even if it is not a common substrate for metabolism, benzene can be oxidized by both <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> and <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>. In bacteria, <a href="/wiki/Dioxygenase" title="Dioxygenase">dioxygenase</a> enzyme can add an <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> to the ring, and the unstable product is immediately reduced (by <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a>) to a cyclic <a href="/wiki/Diol" title="Diol">diol</a> with two double bonds, breaking the aromaticity. Next, the diol is newly reduced by NADH to <a href="/wiki/Catechol" title="Catechol">catechol</a>. The catechol is then metabolized to <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a> and <a href="/wiki/Succinyl_CoA" class="mw-redirect" title="Succinyl CoA">succinyl CoA</a>, used by organisms mainly in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> for energy production. </p><p>The pathway for the metabolism of benzene is complex and begins in the liver. Several enzymes are involved. These include <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> 2E1 (CYP2E1), quinine oxidoreductase (NQ01 or DT-diaphorase or <a href="/wiki/NAD(P)H_dehydrogenase_(quinone_1)" title="NAD(P)H dehydrogenase (quinone 1)">NAD(P)H dehydrogenase (quinone 1)</a>), GSH, and myeloperoxidase (MPO). CYP2E1 is involved at multiple steps: converting benzene to <a href="/wiki/Oxepin" title="Oxepin">oxepin</a> (benzene oxide), <a href="/wiki/Phenol" title="Phenol">phenol</a> to <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a>, and hydroquinone to both benzenetriol and <a href="/wiki/Catechol" title="Catechol">catechol</a>. Hydroquinone, benzenetriol and catechol are converted to polyphenols. In the bone marrow, MPO converts these polyphenols to benzoquinones. These intermediates and metabolites induce genotoxicity by multiple mechanisms including inhibition of <a href="/wiki/Type_II_topoisomerase" title="Type II topoisomerase">topoisomerase II</a> (which maintains chromosome structure), disruption of <a href="/wiki/Microtubules" class="mw-redirect" title="Microtubules">microtubules</a> (which maintains cellular structure and organization), generation of oxygen free radicals (unstable species) that may lead to point mutations, increasing oxidative stress, inducing <a href="/wiki/DNA" title="DNA">DNA</a> strand breaks, and altering DNA <a href="/wiki/Methylation" title="Methylation">methylation</a> (which can affect gene expression). NQ01 and GSH shift metabolism away from toxicity. NQ01 metabolizes <a href="/wiki/Benzoquinone" title="Benzoquinone">benzoquinone</a> toward <a href="/wiki/Polyphenols" class="mw-redirect" title="Polyphenols">polyphenols</a> (counteracting the effect of MPO). GSH is involved with the formation of <a href="/w/index.php?title=Phenylmercapturic_acid&action=edit&redlink=1" class="new" title="Phenylmercapturic acid (page does not exist)">phenylmercapturic acid</a>.<sup id="cite_ref-Smith_2010_133–48_78-1" class="reference"><a href="#cite_note-Smith_2010_133–48-78"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> </p><p>Genetic polymorphisms in these enzymes may induce loss of function or gain of function. For example, mutations in CYP2E1 increase activity and result in increased generation of toxic metabolites. NQ01 mutations result in loss of function and may result in decreased detoxification. Myeloperoxidase mutations result in loss of function and may result in decreased generation of toxic metabolites. GSH mutations or deletions result in loss of function and result in decreased detoxification. These genes may be targets for genetic screening for susceptibility to benzene toxicity.<sup id="cite_ref-101" class="reference"><a href="#cite_note-101"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Molecular_toxicology">Molecular toxicology</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=27" title="Edit section: Molecular toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The paradigm of toxicological assessment of benzene is shifting towards the domain of molecular toxicology as it allows understanding of fundamental biological mechanisms in a better way. <a href="/wiki/Glutathione" title="Glutathione">Glutathione</a> seems to play an important role by protecting against benzene-induced DNA breaks and it is being identified as a new biomarker for exposure and effect.<sup id="cite_ref-r3_102-0" class="reference"><a href="#cite_note-r3-102"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> Benzene causes chromosomal aberrations in the peripheral blood leukocytes and bone marrow explaining the higher incidence of leukemia and multiple myeloma caused by chronic exposure. These aberrations can be monitored using <a href="/wiki/Fluorescent_in_situ_hybridization" class="mw-redirect" title="Fluorescent in situ hybridization">fluorescent in situ hybridization</a> (FISH) with DNA probes to assess the effects of benzene along with the hematological tests as markers of hematotoxicity.<sup id="cite_ref-r1_103-0" class="reference"><a href="#cite_note-r1-103"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may influence susceptibility to the toxic effects of benzene exposure. Individuals carrying variant of NAD(P)H:quinone oxidoreductase 1 (NQO1), microsomal epoxide hydrolase (EPHX) and deletion of the glutathione S-transferase T1 (GSTT1) showed a greater frequency of DNA single-stranded breaks.<sup id="cite_ref-r2_104-0" class="reference"><a href="#cite_note-r2-104"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Biological_oxidation_and_carcinogenic_activity">Biological oxidation and carcinogenic activity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=28" title="Edit section: Biological oxidation and carcinogenic activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>One way of understanding the carcinogenic effects of benzene is by examining the products of biological oxidation. Pure benzene, for example, oxidizes in the body to produce an epoxide, <a href="/wiki/Benzene_oxide" class="mw-redirect" title="Benzene oxide">benzene oxide</a>, which is not excreted readily and can interact with DNA to produce harmful mutations. </p> <div class="mw-heading mw-heading3"><h3 id="Routes_of_exposure">Routes of exposure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=29" title="Edit section: Routes of exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Inhalation">Inhalation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=30" title="Edit section: Inhalation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Outdoor air may contain low levels of benzene from automobile service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions.<sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> About 50% of the entire nationwide (United States) exposure to benzene results from smoking tobacco or from exposure to tobacco smoke.<sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> After smoking 32 cigarettes per day, the smoker would take in about 1.8 milligrams (mg) of benzene. This amount is about 10 times the average daily intake of benzene by nonsmokers.<sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup> </p><p>Inhaled benzene is primarily expelled unchanged through exhalation. In a human study 16.4 to 41.6% of retained benzene was eliminated through the lungs within five to seven hours after a two- to three-hour exposure to 47 to 110 ppm and only 0.07 to 0.2% of the remaining benzene was excreted unchanged in the urine. After exposure to 63 to 405 mg/m<sup>3</sup> of benzene for 1 to 5 hours, 51 to 87% was excreted in the urine as phenol over a period of 23 to 50 hours. In another human study, 30% of absorbed dermally applied benzene, which is primarily metabolized in the liver, was excreted as phenol in the urine.<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Exposure_from_soft_drinks">Exposure from soft drinks</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=31" title="Edit section: Exposure from soft drinks"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Benzene_in_soft_drinks" title="Benzene in soft drinks">Benzene in soft drinks</a></div> <p>Under specific conditions and in the presence of other chemicals <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> (a preservative) and <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> (Vitamin C) may interact to produce benzene. In March 2006, the official <a href="/wiki/Food_Standards_Agency" title="Food Standards Agency">Food Standards Agency</a> in <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> conducted a survey of 150 brands of soft drinks. It found that four contained benzene levels above <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> limits. The affected batches were removed from sale. Similar problems were reported by the FDA in the United States.<sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Contamination_of_water_supply">Contamination of water supply</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=32" title="Edit section: Contamination of water supply"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2005, the water supply to the city of <a href="/wiki/Harbin" title="Harbin">Harbin</a> in China with a population of almost nine million people, was cut off because of a major benzene exposure.<sup id="cite_ref-Guardian-25Nov2005_110-0" class="reference"><a href="#cite_note-Guardian-25Nov2005-110"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> Benzene leaked into the <a href="/wiki/Songhua_River" title="Songhua River">Songhua River</a>, which supplies drinking water to the city, after <a href="/wiki/Jilin_chemical_plant_explosions_2005" class="mw-redirect" title="Jilin chemical plant explosions 2005">an explosion at a China National Petroleum Corporation (CNPC) factory</a> in the city of Jilin on 13 November 2005. </p><p>When plastic water pipes are subject to high heat, the water may be contaminated with benzene.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Genocide">Genocide</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=33" title="Edit section: Genocide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Nazi_Germany" title="Nazi Germany">Nazi Germany</a> used benzene administered via <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a> as one of their many methods for killing.<sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-113" class="reference"><a href="#cite_note-113"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=34" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1266661725">.mw-parser-output .portalbox{padding:0;margin:0.5em 0;display:table;box-sizing:border-box;max-width:175px;list-style:none}.mw-parser-output .portalborder{border:1px solid var(--border-color-base,#a2a9b1);padding:0.1em;background:var(--background-color-neutral-subtle,#f8f9fa)}.mw-parser-output .portalbox-entry{display:table-row;font-size:85%;line-height:110%;height:1.9em;font-style:italic;font-weight:bold}.mw-parser-output .portalbox-image{display:table-cell;padding:0.2em;vertical-align:middle;text-align:center}.mw-parser-output .portalbox-link{display:table-cell;padding:0.2em 0.2em 0.2em 0.3em;vertical-align:middle}@media(min-width:720px){.mw-parser-output .portalleft{margin:0.5em 1em 0.5em 0}.mw-parser-output .portalright{clear:right;float:right;margin:0.5em 0 0.5em 1em}}</style><ul role="navigation" aria-label="Portals" class="noprint portalbox portalborder portalright"> <li class="portalbox-entry"><span class="portalbox-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Aegopodium_podagraria1_ies.jpg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/40px-Aegopodium_podagraria1_ies.jpg" decoding="async" width="32" height="28" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/60px-Aegopodium_podagraria1_ies.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Aegopodium_podagraria1_ies.jpg/120px-Aegopodium_podagraria1_ies.jpg 2x" data-file-width="800" data-file-height="700" /></a></span></span><span class="portalbox-link"><a href="/wiki/Portal:Environment" title="Portal:Environment">Environment portal</a></span></li><li class="portalbox-entry"><span class="portalbox-image"><span class="noviewer" typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/20px-WHO_Rod.svg.png" decoding="async" width="12" height="28" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/40px-WHO_Rod.svg.png 2x" data-file-width="107" data-file-height="250" /></span></span></span><span class="portalbox-link"><a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine portal</a></span></li></ul> <ul><li><a href="/wiki/BTEX" class="mw-redirect" title="BTEX">BTEX</a></li> <li><a href="/wiki/1,2,3-Cyclohexatriene" title="1,2,3-Cyclohexatriene">1,2,3-Cyclohexatriene</a></li> <li><i><a href="/wiki/Industrial_Union_Department_v._American_Petroleum_Institute" title="Industrial Union Department v. American Petroleum Institute">Industrial Union Department v. American Petroleum Institute</a></i></li> <li>Six-membered aromatic rings with one carbon replaced by another element: <a href="/wiki/Borabenzene" title="Borabenzene">borabenzene</a>, <a href="/wiki/Silabenzene" title="Silabenzene">silabenzene</a>, <a href="/wiki/Germabenzene" title="Germabenzene">germabenzene</a>, <a href="/wiki/Stannabenzene" title="Stannabenzene">stannabenzene</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, <a href="/wiki/Phosphorine" title="Phosphorine">phosphorine</a>, <a href="/wiki/Arsabenzene" title="Arsabenzene">arsabenzene</a>, <a href="/wiki/Bismabenzene" title="Bismabenzene">bismabenzene</a>, <a href="/wiki/Pyrylium_salt" class="mw-redirect" title="Pyrylium salt">pyrylium</a>, <a href="/wiki/Thiopyrylium" title="Thiopyrylium">thiopyrylium</a>, <a href="/wiki/Selenopyrylium" title="Selenopyrylium">selenopyrylium</a>, <a href="/wiki/Telluropyrylium" title="Telluropyrylium">telluropyrylium</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Explanatory_notes">Explanatory notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=35" title="Edit section: Explanatory notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"> Dewar included this isomer in a list of possible C6H6 structures in 1869. However, he did not propose it for benzene, and in fact he supported the correct structure proposed by Kekulé. See <a href="/wiki/Dewar_benzene" title="Dewar benzene">Dewar benzene</a> </span> </li> <li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</a></b></span> <span class="reference-text">Critics pointed out a problem with Kekulé's original (1865) structure for benzene: Whenever benzene underwent substitution at the ortho position, two distinguishable isomers should have resulted, depending on whether a double bond or a single bond existed between the carbon atoms to which the substituents were attached; however, no such isomers were observed. In 1872, Kekulé suggested that benzene had two complementary structures and that these forms rapidly interconverted, so that if there were a double bond between any pair of carbon atoms at one instant, that double bond would become a single bond at the next instant (and vice versa). To provide a mechanism for the conversion process, Kekulé proposed that the valency of an atom is determined by the frequency with which it collided with its neighbors in a molecule. As the carbon atoms in the benzene ring collided with each other, each carbon atom would collide twice with one neighbor during a given interval and then twice with its other neighbor during the next interval. Thus, a double bond would exist with one neighbor during the first interval and with the other neighbor during the next interval. Therefore, between the carbon atoms of benzene there were no fixed (i.e., constant) and distinct single or double bonds; instead, the bonds between the carbon atoms were identical. See <a class="external text" href="https://de.wikipedia.org/w/index.php?title=Datei:Kekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf&page=10">pages 86–89</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200320235654/https://de.wikipedia.org/w/index.php?title=Datei%3AKekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf&page=10">Archived</a> 2020-03-20 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> of Auguste Kekulé (1872) "Ueber einige Condensationsprodukte des Aldehyds" (On some condensation products of aldehydes), <i>Liebig's Annalen der Chemie und Pharmacie</i>, <b>162</b>(1): 77–124, 309–320. From p. 89: <i>"Das einfachste Mittel aller Stöße eines Kohlenstoffatoms ergiebt sich aus der Summe der Stöße der beiden ersten Zeiteinheiten, die sich dann periodisch wiederholen. ... man sieht daher, daß jedes Kohlenstoffatom mit den beiden anderen, ... daß diese Verschiedenheit nur eine scheinbare, aber keine wirkliche ist."</i> (The simplest average of all the collisions of a carbon atom [in benzene] comes from the sum of the collisions during the first two units of time, which then periodically repeat. ... thus one sees that each carbon atom collides equally often with the two others against which it bumps, [and] thus stands in exactly the same relation with its two neighbors. The usual structural formula for benzene expresses, of course, only the collisions that occur during <i>one</i> unit of time, thus during one phase, and so one is led to the view [that] doubly substituted derivatives [of benzene] must be different at positions 1,2 and 1,6 [of the benzene ring]. If the idea [that was] just presented—or a similar one—can be regarded as correct, then [it] follows therefrom that this difference [between the bonds at positions 1,2 and 1,6] is only an apparent [one], not a real [one].)</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=36" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFavrePowell2014" class="citation book cs1">Favre, Henri A.; Powell, Warren H. (2014). <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: The <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">Royal Society of Chemistry</a>. pp. 10, 22, 204, 494, 577. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=10%2C+22%2C+204%2C+494%2C+577&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=Henri+A.&rft.au=Powell%2C+Warren+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-handbook13-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-handbook13_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLide2005" class="citation book cs1">Lide, D. R., ed. (2005). <i>CRC Handbook of Chemistry and Physics</i> (86th ed.). Boca Raton, Florida: CRC Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8493-0486-5" title="Special:BookSources/0-8493-0486-5"><bdi>0-8493-0486-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.place=Boca+Raton%2C+Florida&rft.edition=86th&rft.pub=CRC+Press&rft.date=2005&rft.isbn=0-8493-0486-5&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArnoldPlankEricksonPike1958" class="citation journal cs1">Arnold, D.; Plank, C.; Erickson, E.; Pike, F. (1958). "Solubility of Benzene in Water". <i><a href="/w/index.php?title=Industrial_%26_Engineering_Chemistry_Chemical_%26_Engineering_Data_Series&action=edit&redlink=1" class="new" title="Industrial & Engineering Chemistry Chemical & Engineering Data Series (page does not exist)">Industrial & Engineering Chemistry Chemical & Engineering Data Series</a></i>. <b>3</b> (2): <span class="nowrap">253–</span>256. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fi460004a016">10.1021/i460004a016</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Industrial+%26+Engineering+Chemistry+Chemical+%26+Engineering+Data+Series&rft.atitle=Solubility+of+Benzene+in+Water&rft.volume=3&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E253-%3C%2Fspan%3E256&rft.date=1958&rft_id=info%3Adoi%2F10.1021%2Fi460004a016&rft.aulast=Arnold&rft.aufirst=D.&rft.au=Plank%2C+C.&rft.au=Erickson%2C+E.&rft.au=Pike%2C+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBreslowGuo1990" class="citation journal cs1">Breslow, R.; Guo, T. (1990). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC53221">"Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers"</a>. <i><a href="/wiki/Proceedings_of_the_National_Academy_of_Sciences_of_the_United_States_of_America" title="Proceedings of the National Academy of Sciences of the United States of America">Proceedings of the National Academy of Sciences of the United States of America</a></i>. <b>87</b> (1): <span class="nowrap">167–</span>9. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1990PNAS...87..167B">1990PNAS...87..167B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.87.1.167">10.1073/pnas.87.1.167</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC53221">53221</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2153285">2153285</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Surface+tension+measurements+show+that+chaotropic+salting-in+denaturants+are+not+just+water-structure+breakers&rft.volume=87&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E167-%3C%2Fspan%3E9&rft.date=1990&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC53221%23id-name%3DPMC&rft_id=info%3Apmid%2F2153285&rft_id=info%3Adoi%2F10.1073%2Fpnas.87.1.167&rft_id=info%3Abibcode%2F1990PNAS...87..167B&rft.aulast=Breslow&rft.aufirst=R.&rft.au=Guo%2C+T.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC53221&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCokerLudwig2007" class="citation book cs1">Coker, A. Kayode; Ludwig, Ernest E. (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=N8RcH8juG_YC&pg=PA114"><i>Ludwig's Applied Process Design for Chemical And Petrochemical Plants</i></a>. Vol. 1. Elsevier. p. 114. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7506-7766-0" title="Special:BookSources/978-0-7506-7766-0"><bdi>978-0-7506-7766-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160312120850/https://books.google.com/books?id=N8RcH8juG_YC&pg=PA114">Archived</a> from the original on 2016-03-12<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-05-31</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ludwig%27s+Applied+Process+Design+for+Chemical+And+Petrochemical+Plants&rft.pages=114&rft.pub=Elsevier&rft.date=2007&rft.isbn=978-0-7506-7766-0&rft.aulast=Coker&rft.aufirst=A.+Kayode&rft.au=Ludwig%2C+Ernest+E.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DN8RcH8juG_YC%26pg%3DPA114&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-chemister-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-chemister_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-chemister_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-chemister_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-chemister_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-chemister_6-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://chemister.ru/Database/properties-en.php?dbid=1&id=644">"Benzol"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140529232137/http://chemister.ru/Database/properties-en.php?dbid=1&id=644">Archived</a> from the original on 2014-05-29<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-05-29</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Benzol&rft_id=http%3A%2F%2Fchemister.ru%2FDatabase%2Fproperties-en.php%3Fdbid%3D1%26id%3D644&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-nist-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-nist_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nist_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-nist_7-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C71432&Mask=FFFF&Units=SI">Benzene</a> in Linstrom, Peter J.; Mallard, William G. (eds.); <i><a rel="nofollow" class="external text" href="http://webbook.nist.gov">NIST Chemistry WebBook</a>, NIST Standard Reference Database Number 69</i>, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-29)</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/12533897">"Benzenium (CID 12533897"</a>. <a href="/wiki/PubChem" title="PubChem">PubChem</a>. February 8, 2007<span class="reference-accessdate">. Retrieved <span class="nowrap">September 18,</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Benzenium+%28CID+12533897&rft.pub=PubChem&rft.date=2007-02-08&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F12533897&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5150480">"Benzenide (CID 5150480)"</a>. <a href="/wiki/PubChem" title="PubChem">PubChem</a>. June 24, 2005<span class="reference-accessdate">. Retrieved <span class="nowrap">September 18,</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Benzenide+%28CID+5150480%29&rft.pub=PubChem&rft.date=2005-06-24&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F5150480&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-sigma-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sigma_10-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a> Co., <a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/sial/401765">Benzene</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201060259/http://www.hmdb.ca/system/metabolites/msds/000/001/365/original/HMDB01505.pdf?1358893540">Archived</a> 2016-12-01 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. Retrieved on 2014-05-29.</span> </li> <li id="cite_note-PGCH-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0049.html">"#0049"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230049&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0049.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://fscimage.fishersci.com/msds/02610.htm">MSDS</a></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/71432.html">"Benzene"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Benzene&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F71432.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/biomonitoring/Benzene_FactSheet.html">"Benzene fact sheet"</a>. <i>CDC</i>. 2 September 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">16 Aug</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=CDC&rft.atitle=Benzene+fact+sheet&rft.date=2021-09-02&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fbiomonitoring%2FBenzene_FactSheet.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShao2022" class="citation news cs1">Shao, Elena (28 June 2022). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2022/06/28/climate/natural-gas-home-toxic-chemicals.html">"Gas Piped into Homes Contains Benzene and Other Risky Chemicals, Study Finds"</a>. <i>The New York Times</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Gas+Piped+into+Homes+Contains+Benzene+and+Other+Risky+Chemicals%2C+Study+Finds&rft.date=2022-06-28&rft.aulast=Shao&rft.aufirst=Elena&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2022%2F06%2F28%2Fclimate%2Fnatural-gas-home-toxic-chemicals.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text">The word "benzoin" is derived from the Arabic expression "<i>luban jawi</i>", or "<a href="/wiki/Frankincense" title="Frankincense">frankincense</a> of <a href="/wiki/Java" title="Java">Java</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMorris1984" class="citation book cs1">Morris, Edwin T. (1984). <i>Fragrance: The Story of Perfume from Cleopatra to Chanel</i>. Charles Scribner's Sons. p. 101. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0684181950" title="Special:BookSources/978-0684181950"><bdi>978-0684181950</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fragrance%3A+The+Story+of+Perfume+from+Cleopatra+to+Chanel&rft.pages=101&rft.pub=Charles+Scribner%27s+Sons&rft.date=1984&rft.isbn=978-0684181950&rft.aulast=Morris&rft.aufirst=Edwin+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-rocke-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-rocke_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-rocke_17-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRocke,_A._J.1985" class="citation journal cs1">Rocke, A. J. (1985). "Hypothesis and Experiment in the Early Development of Kekule's Benzene Theory". <i><a href="/wiki/Annals_of_Science" title="Annals of Science">Annals of Science</a></i>. <b>42</b> (4): <span class="nowrap">355–</span>81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00033798500200411">10.1080/00033798500200411</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annals+of+Science&rft.atitle=Hypothesis+and+Experiment+in+the+Early+Development+of+Kekule%27s+Benzene+Theory&rft.volume=42&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E355-%3C%2Fspan%3E81&rft.date=1985&rft_id=info%3Adoi%2F10.1080%2F00033798500200411&rft.au=Rocke%2C+A.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFaraday,_M.1825" class="citation journal cs1"><a href="/wiki/Michael_Faraday" title="Michael Faraday">Faraday, M.</a> (1825). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k559209/f473.image">"On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat"</a>. <i><a href="/wiki/Philosophical_Transactions_of_the_Royal_Society" title="Philosophical Transactions of the Royal Society">Philosophical Transactions of the Royal Society</a></i>. <b>115</b>: <span class="nowrap">440–</span>466. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1825.0022">10.1098/rstl.1825.0022</a></span>. <a href="/wiki/JSTOR_(identifier)" class="mw-redirect" title="JSTOR (identifier)">JSTOR</a> <a rel="nofollow" class="external text" href="https://www.jstor.org/stable/107752">107752</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201121235017/http://gallica.bnf.fr/ark:/12148/bpt6k559209/f473.image">Archived</a> from the original on 2020-11-21<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-01-15</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society&rft.atitle=On+new+compounds+of+carbon+and+hydrogen%2C+and+on+certain+other+products+obtained+during+the+decomposition+of+oil+by+heat&rft.volume=115&rft.pages=%3Cspan+class%3D%22nowrap%22%3E440-%3C%2Fspan%3E466&rft.date=1825&rft_id=info%3Adoi%2F10.1098%2Frstl.1825.0022&rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F107752%23id-name%3DJSTOR&rft.au=Faraday%2C+M.&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k559209%2Ff473.image&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span> On pages 443–450, Faraday discusses "bicarburet of hydrogen" (benzene). On pages 449–450, he shows that benzene's empirical formula is C<sub>6</sub>H<sub>6</sub>, although he doesn't realize it because he (like most chemists at that time) used the wrong atomic mass for carbon (6 instead of 12).</span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKaiser,_R.1968" class="citation journal cs1">Kaiser, R. (1968). "Bicarburet of Hydrogen. Reappraisal of the Discovery of Benzene in 1825 with the Analytical Methods of 1968". <i>Angewandte Chemie International Edition in English</i>. <b>7</b> (5): <span class="nowrap">345–</span>350. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.196803451">10.1002/anie.196803451</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=Bicarburet+of+Hydrogen.+Reappraisal+of+the+Discovery+of+Benzene+in+1825+with+the+Analytical+Methods+of+1968&rft.volume=7&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E345-%3C%2Fspan%3E350&rft.date=1968&rft_id=info%3Adoi%2F10.1002%2Fanie.196803451&rft.au=Kaiser%2C+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMitscherlich,_E.1834" class="citation journal cs1">Mitscherlich, E. (1834). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JEs9AAAAcAAJ&pg=PA39">"Über das Benzol und die Säuren der Oel- und Talgarten"</a> [On benzol and oily and fatty types of acids]. <i><a href="/wiki/Liebigs_Annalen" title="Liebigs Annalen">Annalen der Pharmacie</a></i>. <b>9</b> (1): <span class="nowrap">39–</span>48. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18340090103">10.1002/jlac.18340090103</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151123133406/https://books.google.com/books?id=JEs9AAAAcAAJ&pg=PA39">Archived</a> from the original on 2015-11-23<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Pharmacie&rft.atitle=%C3%9Cber+das+Benzol+und+die+S%C3%A4uren+der+Oel-+und+Talgarten&rft.volume=9&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E39-%3C%2Fspan%3E48&rft.date=1834&rft_id=info%3Adoi%2F10.1002%2Fjlac.18340090103&rft.au=Mitscherlich%2C+E.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJEs9AAAAcAAJ%26pg%3DPA39&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span> In a footnote on page 43, Liebig, the journal's editor, suggested changing Mitscherlich's original name for benzene (namely, "benzin") to "benzol", because the suffix "-in" suggested that it was an alkaloid (e.g., Chinin (quinine)), which benzene isn't, whereas the suffix "-ol" suggested that it was oily, which benzene is. Thus on page 44, Mitscherlich states: <i>"Da diese Flüssigkeit aus der Benzoësäure gewonnen wird, und wahrscheinlich mit den Benzoylverbindungen im Zusammenhang steht, so gibt man ihr am besten den Namen Benzol, da der Name Benzoïn schon für die mit dem Bittermandelöl isomerische Verbindung von Liebig und Wöhler gewählt worden ist."</i> (Since this liquid [benzene] is obtained from benzoic acid and probably is related to benzoyl compounds, the best name for it is "benzol", since the name "benzoïn" has already been chosen, by Liebig and Wöhler, for the compound that's isomeric with the oil of bitter almonds [benzaldehyde].)</span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text">Laurent, (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique," <i>Annales de Chemie et de Physique</i>, vol. 63, pp. 27–45, see <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Lx0AAAAAMAAJ&pg=PA44">p. 44</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150320073432/http://books.google.com/books?id=Lx0AAAAAMAAJ&pg=PA44">Archived</a> 2015-03-20 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>: <i>"Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage."</i> (I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acids, because benzene is found in illuminating gas.)</span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHofmann1845" class="citation journal cs1 cs1-prop-foreign-lang-source">Hofmann, A. W. (1845). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=E-1AAAAAYAAJ&pg=PA200">"Ueber eine sichere Reaction auf Benzol"</a> [On a reliable test for benzene]. <i>Annalen der Chemie und Pharmacie</i> (in German). <b>55</b> (2): <span class="nowrap">200–</span>205, especially 204–205. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18450550205">10.1002/jlac.18450550205</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151122124839/https://books.google.com/books?id=E-1AAAAAYAAJ&pg=PA200">Archived</a> from the original on 2015-11-22.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Ueber+eine+sichere+Reaction+auf+Benzol&rft.volume=55&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E200-%3C%2Fspan%3E205%2C+especially+204-205&rft.date=1845&rft_id=info%3Adoi%2F10.1002%2Fjlac.18450550205&rft.aulast=Hofmann&rft.aufirst=A.+W.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DE-1AAAAAYAAJ%26pg%3DPA200&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMansfield_Charles_Blachford1849" class="citation journal cs1">Mansfield Charles Blachford (1849). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kD4aAQAAMAAJ&pg=PA162">"Untersuchung des Steinkohlentheers"</a>. <i>Annalen der Chemie und Pharmacie</i>. <b>69</b> (2): <span class="nowrap">162–</span>180. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18490690203">10.1002/jlac.18490690203</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151027022228/https://books.google.com/books?id=kD4aAQAAMAAJ&pg=PA162">Archived</a> from the original on 2015-10-27<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Untersuchung+des+Steinkohlentheers&rft.volume=69&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E162-%3C%2Fspan%3E180&rft.date=1849&rft_id=info%3Adoi%2F10.1002%2Fjlac.18490690203&rft.au=Mansfield+Charles+Blachford&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DkD4aAQAAMAAJ%26pg%3DPA162&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text">Charles Mansfield filed for (November 11, 1847) and received (May 1848) a patent (no. 11,960) for the fractional distillation of coal tar.</span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHoffman,_Augustus_W.1856" class="citation journal cs1">Hoffman, Augustus W. (1856). "On insolinic acid". <i><a href="/wiki/Proceedings_of_the_Royal_Society" title="Proceedings of the Royal Society">Proceedings of the Royal Society</a></i>. <b>8</b>: <span class="nowrap">1–</span>3. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frspl.1856.0002">10.1098/rspl.1856.0002</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:97105342">97105342</a>. <q>The existence and mode of formation of insolinic acid prove that to the series of monobasic aromatic acids, C<sub>n2</sub>H<sub>n2-8</sub>O<sub>4</sub>, the lowest known term of which is benzoic acid, ... .</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Royal+Society&rft.atitle=On+insolinic+acid&rft.volume=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E3&rft.date=1856&rft_id=info%3Adoi%2F10.1098%2Frspl.1856.0002&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A97105342%23id-name%3DS2CID&rft.au=Hoffman%2C+Augustus+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span> [Note: The empirical formulas of organic compounds that appear in Hofmann's article (p. 3) are based upon an atomic mass of carbon of 6 (instead of 12) and an atomic mass of oxygen of 8 (instead of 16).]</span> </li> <li id="cite_note-Cernicharo_546-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-Cernicharo_546_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCernicharoHerasTielensPardo2001" class="citation cs2">Cernicharo, José; et al. (2001), "Infrared Space Observatory's Discovery of C<sub>4</sub>H<sub>2</sub>, C<sub>6</sub>H<sub>2</sub>, and Benzene in CRL 618", <i>Astrophysical Journal Letters</i>, <b>546</b> (2): <span class="nowrap">L123 –</span> <span class="nowrap">L126</span>, <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2001ApJ...546L.123C">2001ApJ...546L.123C</a>, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F318871">10.1086/318871</a></span></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Astrophysical+Journal+Letters&rft.atitle=Infrared+Space+Observatory%27s+Discovery+of+C%3Csub%3E4%3C%2Fsub%3EH%3Csub%3E2%3C%2Fsub%3E%2C+C%3Csub%3E6%3C%2Fsub%3EH%3Csub%3E2%3C%2Fsub%3E%2C+and+Benzene+in+CRL+618&rft.volume=546&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3EL123+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3EL126%3C%2Fspan%3E&rft.date=2001&rft_id=info%3Adoi%2F10.1086%2F318871&rft_id=info%3Abibcode%2F2001ApJ...546L.123C&rft.aulast=Cernicharo&rft.aufirst=Jos%C3%A9&rft.au=Heras%2C+Ana+M.&rft.au=Tielens%2C+A.+G.+G.+M.&rft.au=Pardo%2C+Juan+R.&rft.au=Herpin%2C+Fabrice&rft.au=Gu%C3%A9lin%2C+Michel&rft.au=Waters%2C+L.+B.+F.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text">Claus, Adolph K.L. (1867) "Theoretische Betrachtungen und deren Anwendungen zur Systematik der organischen Chemie" (Theoretical considerations and their applications to the classification scheme of organic chemistry), <i>Berichte über die Verhandlungen der Naturforschenden Gesellschaft zu Freiburg im Breisgau</i> (<a href="/w/index.php?title=Reports_of_the_Proceedings_of_the_Scientific_Society_of_Freiburg&action=edit&redlink=1" class="new" title="Reports of the Proceedings of the Scientific Society of Freiburg (page does not exist)">Reports of the Proceedings of the Scientific Society of Freiburg</a> in Breisgau), <b>4</b> : 116–381. In the section <i>Aromatischen Verbindungen</i> (aromatic compounds), pp. 315–347, Claus presents Kekulé's hypothetical structure for benzene (<a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0339">p. 317</a>), presents objections to it, presents an alternative geometry (<a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0342">p. 320</a>), and concludes that his alternative is correct (<a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0348">p. 326</a>). See also figures on <a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0021&physid=PHYS_0376">p. 354</a> or <a rel="nofollow" class="external text" href="http://gdz.sub.uni-goettingen.de/en/dms/loader/img/?PID=PPN623920514_0004%7CLOG_0023&physid=PHYS_0401">p. 379.</a></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDewar_James1869" class="citation journal cs1">Dewar James (1869). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PmlUAAAAIAAJ&pg=PA82">"On the oxidation of phenyl alcohol, and a mechanical arrangement adapted to illustrate structure in the non-saturated hydrocarbons"</a>. <i><a href="/wiki/Proceedings_of_the_Royal_Society_of_Edinburgh" class="mw-redirect" title="Proceedings of the Royal Society of Edinburgh">Proceedings of the Royal Society of Edinburgh</a></i>. <b>6</b>: <span class="nowrap">82–</span>86. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FS0370164600045387">10.1017/S0370164600045387</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151124162938/https://books.google.com/books?id=PmlUAAAAIAAJ&pg=PA82">Archived</a> from the original on 2015-11-24<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Royal+Society+of+Edinburgh&rft.atitle=On+the+oxidation+of+phenyl+alcohol%2C+and+a+mechanical+arrangement+adapted+to+illustrate+structure+in+the+non-saturated+hydrocarbons&rft.volume=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E82-%3C%2Fspan%3E86&rft.date=1869&rft_id=info%3Adoi%2F10.1017%2FS0370164600045387&rft.au=Dewar+James&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPmlUAAAAIAAJ%26pg%3DPA82&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLadenburg_Albert1869" class="citation journal cs1">Ladenburg Albert (1869). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Epg8AAAAIAAJ&pg=PA140">"Bemerkungen zur aromatischen Theorie"</a> [Observations on the aromatic theory]. <i>Berichte der Deutschen Chemischen Gesellschaft</i>. <b>2</b>: <span class="nowrap">140–</span>142. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.18690020171">10.1002/cber.18690020171</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151122175439/https://books.google.com/books?id=Epg8AAAAIAAJ&pg=PA140">Archived</a> from the original on 2015-11-22<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Bemerkungen+zur+aromatischen+Theorie&rft.volume=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E140-%3C%2Fspan%3E142&rft.date=1869&rft_id=info%3Adoi%2F10.1002%2Fcber.18690020171&rft.au=Ladenburg+Albert&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEpg8AAAAIAAJ%26pg%3DPA140&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-Kekulé1865-31"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kekulé1865_31-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kekulé1865_31-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKekulé,_F._A.1865" class="citation journal cs1"><a href="/wiki/Friedrich_August_Kekul%C3%A9_von_Stradonitz" class="mw-redirect" title="Friedrich August Kekulé von Stradonitz">Kekulé, F. A.</a> (1865). <a rel="nofollow" class="external text" href="https://gallica.bnf.fr/ark:/12148/bpt6k281952v/f102">"Sur la constitution des substances aromatiques"</a>. <i>Bulletin de la Société Chimique de Paris</i>. <b>3</b>: <span class="nowrap">98–</span>110. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151114102723/https://books.google.com/books?id=bFsSAAAAYAAJ&pg=PA98">Archived</a> from the original on 2015-11-14<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+de+la+Soci%C3%A9t%C3%A9+Chimique+de+Paris&rft.atitle=Sur+la+constitution+des+substances+aromatiques&rft.volume=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E98-%3C%2Fspan%3E110&rft.date=1865&rft.au=Kekul%C3%A9%2C+F.+A.&rft_id=https%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k281952v%2Ff102&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span> On p. 100, Kekulé suggests that the carbon atoms of benzene could form a "chaîne fermée" (closed chain).</span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAug._Kekulé1872" class="citation cs2 cs1-prop-foreign-lang-source">Aug. Kekulé (1872), <a class="external text" href="https://upload.wikimedia.org/wikipedia/commons/5/5d/Kekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf">"Ueber einige Condensationsproducte des Aldehyds"</a> <span class="cs1-format">(PDF)</span>, <i><a href="/wiki/Annalen_der_Chemie_und_Pharmacie" class="mw-redirect" title="Annalen der Chemie und Pharmacie">Annalen der Chemie und Pharmacie</a></i> (in German), vol. 162, no. 1, pp. 77–124, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18721620110">10.1002/jlac.18721620110</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Chemie+und+Pharmacie&rft.atitle=Ueber+einige+Condensationsproducte+des+Aldehyds&rft.volume=162&rft.issue=1&rft.pages=pp.-77-124&rft.date=1872&rft_id=info%3Adoi%2F10.1002%2Fjlac.18721620110&rft.au=Aug.+Kekul%C3%A9&rft_id=https%3A%2F%2Fupload.wikimedia.org%2Fwikipedia%2Fcommons%2F5%2F5d%2FKekule_-_Ueber_einige_Condensationsproducte_des_Aldehyds.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArmstrong_Henry_E1887" class="citation journal cs1">Armstrong Henry E (1887). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4QbzAAAAMAAJ&pg=PA258">"An explanation of the laws which govern substitution in the case of benzenoid compounds"</a>. <i>Journal of the Chemical Society</i>. <b>51</b>: 258–268 [264]. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fct8875100258">10.1039/ct8875100258</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151022073257/https://books.google.com/books?id=4QbzAAAAMAAJ&pg=PA258">Archived</a> from the original on 2015-10-22<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society&rft.atitle=An+explanation+of+the+laws+which+govern+substitution+in+the+case+of+benzenoid+compounds&rft.volume=51&rft.pages=258-268+264&rft.date=1887&rft_id=info%3Adoi%2F10.1039%2Fct8875100258&rft.au=Armstrong+Henry+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4QbzAAAAMAAJ%26pg%3DPA258&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text">In his 1890 paper, Armstrong represented benzene nuclei within polycyclic benzenoids by placing inside the benzene nuclei a letter "C", an abbreviation of the word "centric". Centric affinities (i.e., bonds) acted within a designated cycle of carbon atoms. From p. 102: " ... benzene, according to this view, may be represented by a double ring, in fact." See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">Armstrong, H.E. (1890). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=pst.000052368141;view=1up;seq=319">"The structure of cycloid hydrocarbons"</a>. <i><a href="/wiki/Proceedings_of_the_Chemical_Society" title="Proceedings of the Chemical Society">Proceedings of the Chemical Society</a></i>. <b>6</b>: <span class="nowrap">101–</span>105. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211116024104/https://babel.hathitrust.org/cgi/pt?id=pst.000052368141;view=1up;seq=319">Archived</a> from the original on 2021-11-16<span class="reference-accessdate">. Retrieved <span class="nowrap">2018-02-17</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Chemical+Society&rft.atitle=The+structure+of+cycloid+hydrocarbons&rft.volume=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E101-%3C%2Fspan%3E105&rft.date=1890&rft.aulast=Armstrong&rft.aufirst=H.E.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dpst.000052368141%3Bview%3D1up%3Bseq%3D319&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></li></ul> The use of a circle to denote a benzene nucleus first appeared in: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">Armit, James Wilson; Robinson, Robert (1925). "Polynuclear heterocyclic aromatic types. Part II. Some anhydronium bases". <i>Journal of the Chemical Society, Transactions</i>. <b>127</b>: <span class="nowrap">1604–</span>1618. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fct9252701604">10.1039/ct9252701604</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society%2C+Transactions&rft.atitle=Polynuclear+heterocyclic+aromatic+types.+Part+II.+Some+anhydronium+bases&rft.volume=127&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1604-%3C%2Fspan%3E1618&rft.date=1925&rft_id=info%3Adoi%2F10.1039%2Fct9252701604&rft.aulast=Armit&rft.aufirst=James+Wilson&rft.au=Robinson%2C+Robert&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></li></ul> A history of the determination of benzene's structure is recounted in: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">Balaban, Alexandru T.; Schleyer, Paul v. R.; Rzepa, Henry S. (2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr0300946">"Crocker, Not Armit and Robinson, Begat the Six Aromatic Electrons"</a>. <i>Chemical Reviews</i>. <b>105</b> (10): <span class="nowrap">3436–</span>3447. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr0300946">10.1021/cr0300946</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16218557">16218557</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Crocker%2C+Not+Armit+and+Robinson%2C+Begat+the+Six+Aromatic+Electrons&rft.volume=105&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3436-%3C%2Fspan%3E3447&rft.date=2005&rft_id=info%3Adoi%2F10.1021%2Fcr0300946&rft_id=info%3Apmid%2F16218557&rft.aulast=Balaban&rft.aufirst=Alexandru+T.&rft.au=Schleyer%2C+Paul+v.+R.&rft.au=Rzepa%2C+Henry+S.&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%252Fcr0300946&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></li></ul> </span></li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAdolf_Baeyer1888" class="citation cs2 cs1-prop-foreign-lang-source">Adolf Baeyer (1888), <a rel="nofollow" class="external text" href="https://zenodo.org/record/1851261">"Über die Constitution des Benzols"</a>, <i><a href="/wiki/Justus_Liebigs_Annalen_der_Chemie" class="mw-redirect" title="Justus Liebigs Annalen der Chemie">Justus Liebigs Annalen der Chemie</a></i> (in German), vol. 245, no. <span class="nowrap">1–</span>2, pp. 103–190, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18882450110">10.1002/jlac.18882450110</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Justus+Liebigs+Annalen+der+Chemie&rft.atitle=%C3%9Cber+die+Constitution+des+Benzols&rft.volume=245&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=pp.-103-190&rft.date=1888&rft_id=info%3Adoi%2F10.1002%2Fjlac.18882450110&rft.au=Adolf+Baeyer&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1851261&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text">Thiele, Johannes (1899) "Zur Kenntnis der ungesättigten Verbindungen" (On our knowledge of unsaturated compounds), <i>Justus Liebig's Annalen der Chemie</i><b>306</b>: 87–142; see: <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NYw8AAAAIAAJ&pg=RA1-PA125">"VIII. Die aromatischen Verbindungen. Das Benzol." (VIII. The aromatic compounds. Benzene.), pp. 125–129.</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200310154749/https://books.google.com/books?id=NYw8AAAAIAAJ&pg=RA1-PA125">Archived</a> 2020-03-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> See further: Thiele (1901) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hx3kjj;view=1up;seq=543">"Zur Kenntnis der ungesättigen Verbindungen,"</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211226183108/https://babel.hathitrust.org/cgi/pt?id=hvd.hx3kjj;view=1up;seq=543">Archived</a> 2021-12-26 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> <i>Justus Liebig's Annalen der Chemie</i>, <b>319</b>: 129–143.</span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLoschmidt1861" class="citation book cs1 cs1-prop-foreign-lang-source">Loschmidt, J. (1861). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ksw5AAAAcAAJ&pg=PA30"><i>Chemische Studien</i></a> (in German). Vienna, Austria-Hungary: Carl Gerold's Sohn. pp. 30, 65. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160507144736/https://books.google.com/books?id=ksw5AAAAcAAJ&pg=PA30">Archived</a> from the original on 2016-05-07<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemische+Studien&rft.place=Vienna%2C+Austria-Hungary&rft.pages=30%2C+65&rft.pub=Carl+Gerold%27s+Sohn&rft.date=1861&rft.aulast=Loschmidt&rft.aufirst=J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dksw5AAAAcAAJ%26pg%3DPA30&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKekulé,_F._A.1866" class="citation journal cs1">Kekulé, F. A. (1866). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=pNryAAAAMAAJ&pg=PA129">"Untersuchungen über aromatische Verbindungen (Investigations of aromatic compounds)"</a>. <i>Liebigs Annalen der Chemie und Pharmacie</i>. <b>137</b> (2): <span class="nowrap">129–</span>36. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18661370202">10.1002/jlac.18661370202</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211226183108/https://books.google.com/books?id=pNryAAAAMAAJ&pg=PA129">Archived</a> from the original on 2021-12-26<span class="reference-accessdate">. Retrieved <span class="nowrap">2021-12-25</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Liebigs+Annalen+der+Chemie+und+Pharmacie&rft.atitle=Untersuchungen+%C3%BCber+aromatische+Verbindungen+%28Investigations+of+aromatic+compounds%29&rft.volume=137&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E129-%3C%2Fspan%3E36&rft.date=1866&rft_id=info%3Adoi%2F10.1002%2Fjlac.18661370202&rft.au=Kekul%C3%A9%2C+F.+A.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DpNryAAAAMAAJ%26pg%3DPA129&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRocke2010" class="citation book cs1">Rocke, A. J. (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=U5iHmP_dTLwC&pg=PA186"><i>Image and Reality: Kekule, Kopp, and the Scientific Imagination</i></a>. University of Chicago Press. pp. <span class="nowrap">186–</span>227. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0226723358" title="Special:BookSources/978-0226723358"><bdi>978-0226723358</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200727092623/https://books.google.com/books?id=U5iHmP_dTLwC&pg=PA186">Archived</a> from the original on 2020-07-27<span class="reference-accessdate">. Retrieved <span class="nowrap">2020-05-15</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Image+and+Reality%3A+Kekule%2C+Kopp%2C+and+the+Scientific+Imagination&rft.pages=%3Cspan+class%3D%22nowrap%22%3E186-%3C%2Fspan%3E227&rft.pub=University+of+Chicago+Press&rft.date=2010&rft.isbn=978-0226723358&rft.aulast=Rocke&rft.aufirst=A.+J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DU5iHmP_dTLwC%26pg%3DPA186&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRead1995" class="citation book cs1">Read, John (1995). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/fromalchemytoche00read_063"><i>From alchemy to chemistry</i></a></span>. New York: Dover Publications. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/fromalchemytoche00read_063/page/n210">179</a>–180. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780486286907" title="Special:BookSources/9780486286907"><bdi>9780486286907</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=From+alchemy+to+chemistry&rft.place=New+York&rft.pages=179-180&rft.pub=Dover+Publications&rft.date=1995&rft.isbn=9780486286907&rft.aulast=Read&rft.aufirst=John&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Ffromalchemytoche00read_063&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text">English translation <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWilcoxGreenbaum1965" class="citation journal cs1">Wilcox, David H.; Greenbaum, Frederick R. (1965). "Kekule's benzene ring theory: A subject for lighthearted banter". <i>Journal of Chemical Education</i>. <b>42</b> (5): <span class="nowrap">266–</span>67. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1965JChEd..42..266W">1965JChEd..42..266W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed042p266">10.1021/ed042p266</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=Kekule%27s+benzene+ring+theory%3A+A+subject+for+lighthearted+banter&rft.volume=42&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E266-%3C%2Fspan%3E67&rft.date=1965&rft_id=info%3Adoi%2F10.1021%2Fed042p266&rft_id=info%3Abibcode%2F1965JChEd..42..266W&rft.aulast=Wilcox&rft.aufirst=David+H.&rft.au=Greenbaum%2C+Frederick+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKekulé,_F._A.1890" class="citation journal cs1">Kekulé, F. A. (1890). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90720c/f1304.chemindefer">"Benzolfest: Rede"</a>. <i>Berichte der Deutschen Chemischen Gesellschaft</i>. <b>23</b>: <span class="nowrap">1302–</span>11. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.189002301204">10.1002/cber.189002301204</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070516101338/http://gallica.bnf.fr/ark:/12148/bpt6k90720c/f1304.chemindefer">Archived</a> from the original on 2007-05-16<span class="reference-accessdate">. Retrieved <span class="nowrap">2007-03-12</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Benzolfest%3A+Rede&rft.volume=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1302-%3C%2Fspan%3E11&rft.date=1890&rft_id=info%3Adoi%2F10.1002%2Fcber.189002301204&rft.au=Kekul%C3%A9%2C+F.+A.&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k90720c%2Ff1304.chemindefer&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBenfey_O._T.1958" class="citation journal cs1">Benfey O. T. (1958). "August Kekulé and the Birth of the Structural Theory of Organic Chemistry in 1858". <i>Journal of Chemical Education</i>. <b>35</b> (1): <span class="nowrap">21–</span>23. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1958JChEd..35...21B">1958JChEd..35...21B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed035p21">10.1021/ed035p21</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=August+Kekul%C3%A9+and+the+Birth+of+the+Structural+Theory+of+Organic+Chemistry+in+1858&rft.volume=35&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E21-%3C%2Fspan%3E23&rft.date=1958&rft_id=info%3Adoi%2F10.1021%2Fed035p21&rft_id=info%3Abibcode%2F1958JChEd..35...21B&rft.au=Benfey+O.+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGillis_Jean1966" class="citation journal cs1">Gillis Jean (1966). 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(2021). <a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FD0EW00836B">"Drinking water contamination from the thermal degradation of plastics: Implications for wildfire and structure fire response"</a>. <i>Environmental Science: Water Research & Technology</i>. <b>7</b> (2): <span class="nowrap">274–</span>284. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FD0EW00836B">10.1039/D0EW00836B</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Science%3A+Water+Research+%26+Technology&rft.atitle=Drinking+water+contamination+from+the+thermal+degradation+of+plastics%3A+Implications+for+wildfire+and+structure+fire+response&rft.volume=7&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E274-%3C%2Fspan%3E284&rft.date=2021&rft_id=info%3Adoi%2F10.1039%2FD0EW00836B&rft.aulast=Isaacson&rft.aufirst=Kristofer+P.&rft.au=Proctor%2C+Caitlin+R.&rft.au=Wang%2C+Q.+Erica&rft.au=Edwards%2C+Ethan+Y.&rft.au=Noh%2C+Yoorae&rft.au=Shah%2C+Amisha+D.&rft.au=Whelton%2C+Andrew+J.&rft_id=https%3A%2F%2Fdoi.org%2F10.1039%252FD0EW00836B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-112"><span class="mw-cite-backlink"><b><a href="#cite_ref-112">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://auschwitz.org/en/history/camp-hospitals/selections-and-lethal-injections/">"Selections and lethal injections"</a>. <i><a href="/wiki/Auschwitz-Birkenau_State_Museum" title="Auschwitz-Birkenau State Museum">Auschwitz-Birkenau State Museum</a></i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200509105620/http://auschwitz.org/en/history/camp-hospitals/selections-and-lethal-injections">Archived</a> from the original on May 9, 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">May 15,</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Auschwitz-Birkenau+State+Museum&rft.atitle=Selections+and+lethal+injections&rft_id=http%3A%2F%2Fauschwitz.org%2Fen%2Fhistory%2Fcamp-hospitals%2Fselections-and-lethal-injections%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> <li id="cite_note-113"><span class="mw-cite-backlink"><b><a href="#cite_ref-113">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.haaretz.com/world-news/europe/.premium-austria-s-former-nazi-labor-camp-that-s-billed-as-a-tourist-site-1.7195524">"A Former Nazi Labor Camp in Austria, Now Billed as a Tourist Site"</a>. <i>Haaretz</i>. May 3, 2019. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190511075141/https://www.haaretz.com/world-news/europe/.premium-austria-s-former-nazi-labor-camp-that-s-billed-as-a-tourist-site-1.7195524">Archived</a> from the original on May 11, 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">May 11,</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Haaretz&rft.atitle=A+Former+Nazi+Labor+Camp+in+Austria%2C+Now+Billed+as+a+Tourist+Site&rft.date=2019-05-03&rft_id=https%3A%2F%2Fwww.haaretz.com%2Fworld-news%2Feurope%2F.premium-austria-s-former-nazi-labor-camp-that-s-billed-as-a-tourist-site-1.7195524&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzene" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzene&action=edit&section=37" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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href="https://commons.wikimedia.org/wiki/Benzene" class="extiw" title="commons:Benzene"><span style="font-style:italic; font-weight:bold;">Benzene</span></a> (<a href="https://commons.wikimedia.org/wiki/Category:Benzene" class="extiw" title="commons:Category:Benzene">category</a>)</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735" /><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wiktionary-logo-en-v2.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/benzene" class="extiw" title="wiktionary:benzene">benzene</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735" /><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wikiquote-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></a></span></div> <div class="side-box-text plainlist">Wikiquote has quotations related to <i><b><a href="https://en.wikiquote.org/wiki/Special:Search/Benzene" class="extiw" title="q:Special:Search/Benzene">Benzene</a></b></i>.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985" /><div class="side-box metadata side-box-right"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/40px-Scholia_logo.svg.png" decoding="async" width="40" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/60px-Scholia_logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/80px-Scholia_logo.svg.png 2x" data-file-width="107" data-file-height="104" /></span></span></div> <div class="side-box-text plainlist"><a href="https://www.wikidata.org/wiki/Wikidata:Scholia" class="extiw" title="d:Wikidata:Scholia">Scholia</a> has a <i>chemical</i> profile for <i><b><a href="https://iw.toolforge.org/scholia/chemical/Q2270" class="extiw" title="toolforge:scholia/chemical/Q2270">Benzene</a></b></i>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_benzene.htm">Benzene</a> at <i><a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic Table of Videos">The Periodic Table of Videos</a></i> (University of Nottingham)</li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0015.htm">International Chemical Safety Card 0015</a></li> <li><a rel="nofollow" class="external text" href="http://www.epa.gov/iris/subst/0276.htm">USEPA Summary of Benzene Toxicity</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0049.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/241">Benzene</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070301122020/http://ntp.niehs.nih.gov/index.cfm?objectid=0707525C-0F07-05BF-A16CAC7B0ECC97B5">Dept. of Health and Human Services: TR-289: Toxicology and Carcinogenesis Studies of Benzene</a></li> <li><a rel="nofollow" class="external text" href="http://www.ch.ic.ac.uk/video/faraday_l.m4v">Video Recording</a> of Sir John Cadogan giving a lecture on Benzene at the Royal Institution, 22nd September 1991</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070224171424/http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s019benz.pdf">Substance profile</a></li> <li><a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+35">NLM Hazardous Substances Databank – Benzene</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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<li><a href="/wiki/Cyclodecapentaene" title="Cyclodecapentaene">Cyclodecapentaene</a></li> <li><a href="/wiki/Cyclododecahexaene" title="Cyclododecahexaene">Cyclododecahexaene</a></li> <li><i><a href="/wiki/Cyclotetradecaheptaene" title="Cyclotetradecaheptaene">Cyclotetradecaheptaene</a></i></li> <li><a href="/wiki/Cyclohexadecaoctaene" class="mw-redirect" title="Cyclohexadecaoctaene">Cyclohexadecaoctaene</a></li> <li><i><a href="/wiki/Cyclooctadecanonaene" title="Cyclooctadecanonaene">Cyclooctadecanonaene</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Odd–numbered</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">Cyclopentadiene</a></li> <li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">Cycloheptatriene</a></li> <li><a href="/wiki/Cyclononatetraene" title="Cyclononatetraene">Cyclononatetraene</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>Compounds in <i>italics</i> are <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Cycloalkenes57" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cycloalkenes" title="Template:Cycloalkenes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cycloalkenes" title="Template talk:Cycloalkenes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cycloalkenes" title="Special:EditPage/Template:Cycloalkenes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cycloalkenes57" style="font-size:114%;margin:0 4em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkene" title="Alkene">Alkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclobutadiene" title="Cyclobutadiene">Cyclobutadiene</a></li> <li><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">Cyclopentadiene</a></li> <li>Cyclohexadiene <ul><li><a href="/wiki/1,3-Cyclohexadiene" class="mw-redirect" title="1,3-Cyclohexadiene">1,3-Cyclohexadiene</a></li> <li><a href="/wiki/1,4-Cyclohexadiene" class="mw-redirect" title="1,4-Cyclohexadiene">1,4-Cyclohexadiene</a></li></ul></li> <li>Cycloheptadiene <ul><li><a href="/wiki/1,3-Cycloheptadiene" title="1,3-Cycloheptadiene">1,3-Cycloheptadiene</a></li> <li><a href="/wiki/1,4-Cycloheptadiene" title="1,4-Cycloheptadiene">1,4-Cycloheptadiene</a></li></ul></li> <li><a href="/wiki/Cyclooctadiene" title="Cyclooctadiene">Cyclooctadiene</a> <ul><li><a href="/wiki/1,5-Cyclooctadiene" title="1,5-Cyclooctadiene">1,5-Cyclooctadiene</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triene" class="mw-redirect" title="Triene">Trienes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Benzene</a></li> <li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">Cycloheptatriene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetraenes</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclononatetraene" title="Cyclononatetraene">Cyclononatetraene</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Hydrocarbons181" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:azzurro;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrocarbons" title="Template:Hydrocarbons"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrocarbons" title="Template talk:Hydrocarbons"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrocarbons" title="Special:EditPage/Template:Hydrocarbons"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons181" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Saturated<br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="AlkanesCnH2n_+_2135" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups729" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li> <li><a href="/wiki/Thia-crown_ether" title="Thia-crown ether">Thia-crown ether</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="GABAA_receptor_positive_modulators746" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABAA_receptor_positive_modulators" title="Template talk:GABAA receptor positive modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABAA_receptor_positive_modulators" title="Special:EditPage/Template:GABAA receptor positive modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABAA_receptor_positive_modulators746" style="font-size:114%;margin:0 4em"><a href="/wiki/GABAA_receptor_positive_allosteric_modulator" title="GABAA receptor positive allosteric modulator"><abbr title="γ-Aminobutyric acid">GABA</abbr><sub>A</sub> receptor positive modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">Brometone</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">Butanol</a></li> <li><a href="/wiki/Chloralodol" title="Chloralodol">Chloralodol</a></li> <li><a href="/wiki/Chlorobutanol" title="Chlorobutanol">Chlorobutanol (cloretone)</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>)</li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">Pentanol</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">Propanol</a></li> <li><a href="/wiki/Tert-Butanol" class="mw-redirect" title="Tert-Butanol"><i>tert</i>-Butanol (2M2P)</a></li> <li><a href="/wiki/Tert-Pentanol" class="mw-redirect" title="Tert-Pentanol"><i>tert</i>-Pentanol (2M2B)</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li> <li><a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">Trifluoroethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric_acid" class="mw-redirect" title="(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid">(-)-DMBB</a></li> <li><a href="/wiki/Allobarbital" title="Allobarbital">Allobarbital</a></li> <li><a href="/wiki/Alphenal" title="Alphenal">Alphenal</a></li> <li><a href="/wiki/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Aprobarbital" title="Aprobarbital">Aprobarbital</a></li> <li><a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Barbital" title="Barbital">Barbital</a></li> <li><a href="/wiki/Benzobarbital" title="Benzobarbital">Benzobarbital</a></li> <li><a href="/wiki/Benzylbutylbarbiturate" title="Benzylbutylbarbiturate">Benzylbutylbarbiturate</a></li> <li><a href="/wiki/Brallobarbital" title="Brallobarbital">Brallobarbital</a></li> <li><a href="/wiki/Brophebarbital" title="Brophebarbital">Brophebarbital</a></li> <li><a href="/wiki/Butabarbital" title="Butabarbital">Butabarbital/Secbutabarbital</a></li> <li><a href="/wiki/Butalbital" title="Butalbital">Butalbital</a></li> <li><a href="/wiki/Buthalital" title="Buthalital">Buthalital</a></li> <li><a href="/wiki/Butobarbital" title="Butobarbital">Butobarbital</a></li> <li><a href="/wiki/Butallylonal" title="Butallylonal">Butallylonal</a></li> <li><a href="/wiki/Carbubarb" title="Carbubarb">Carbubarb</a></li> <li><a href="/wiki/Crotylbarbital" title="Crotylbarbital">Crotylbarbital</a></li> <li><a href="/wiki/Cyclobarbital" title="Cyclobarbital">Cyclobarbital</a></li> <li><a href="/wiki/Cyclopentobarbital" title="Cyclopentobarbital">Cyclopentobarbital</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Enallylpropymal" title="Enallylpropymal">Enallylpropymal</a></li> <li><a href="/wiki/Ethallobarbital" title="Ethallobarbital">Ethallobarbital</a></li> <li><a href="/wiki/Eterobarb" title="Eterobarb">Eterobarb</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Heptabarb" title="Heptabarb">Heptabarb</a></li> <li><a href="/wiki/Heptobarbital" title="Heptobarbital">Heptobarbital</a></li> <li><a href="/wiki/Hexethal" title="Hexethal">Hexethal</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methitural" title="Methitural">Methitural</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Nealbarbital" title="Nealbarbital">Nealbarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenallymal" class="mw-redirect" title="Phenallymal">Phenallymal</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phetharbital" title="Phetharbital">Phetharbital</a></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a></li> <li><a href="/wiki/Probarbital" title="Probarbital">Probarbital</a></li> <li><a href="/wiki/Propallylonal" title="Propallylonal">Propallylonal</a></li> <li><a href="/wiki/Propylbarbital" title="Propylbarbital">Propylbarbital</a></li> <li><a href="/wiki/Proxibarbital" title="Proxibarbital">Proxibarbital</a></li> <li><a href="/wiki/Reposal" title="Reposal">Reposal</a></li> <li><a href="/wiki/Secobarbital" title="Secobarbital">Secobarbital</a></li> <li><a href="/wiki/Sigmodal" title="Sigmodal">Sigmodal</a></li> <li><a href="/wiki/Spirobarbital" title="Spirobarbital">Spirobarbital</a></li> <li><a href="/wiki/Talbutal" title="Talbutal">Talbutal</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tetrabarbital" title="Tetrabarbital">Tetrabarbital</a></li> <li><a href="/wiki/Thialbarbital" title="Thialbarbital">Thialbarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Thiobarbital" title="Thiobarbital">Thiobarbital</a></li> <li><a href="/wiki/Thiobutabarbital" title="Thiobutabarbital">Thiobutabarbital</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li> <li><a href="/wiki/Valofane" title="Valofane">Valofane</a></li> <li><a href="/wiki/Vinbarbital" title="Vinbarbital">Vinbarbital</a></li> <li><a href="/wiki/Vinylbital" title="Vinylbital">Vinylbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Oxoquazepam" title="2-Oxoquazepam">2-Oxoquazepam</a></li> <li><a href="/wiki/3-Hydroxyphenazepam" title="3-Hydroxyphenazepam">3-Hydroxyphenazepam</a></li> <li><a href="/wiki/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a href="/wiki/Alprazolam" title="Alprazolam">Alprazolam</a></li> <li><a href="/wiki/Arfendazam" title="Arfendazam">Arfendazam</a></li> <li><a href="/wiki/Avizafone" title="Avizafone">Avizafone</a></li> <li><a href="/wiki/Bentazepam" title="Bentazepam">Bentazepam</a></li> <li><a href="/wiki/Bretazenil" title="Bretazenil">Bretazenil</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/Bromazolam" title="Bromazolam">Bromazolam</a></li> <li><a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Carburazepam" title="Carburazepam">Carburazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Ciclotizolam" title="Ciclotizolam">Ciclotizolam</a></li> <li><a href="/wiki/Cinazepam" title="Cinazepam">Cinazepam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Clazolam" title="Clazolam">Clazolam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Cloniprazepam" title="Cloniprazepam">Cloniprazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/CP-1414S" title="CP-1414S">CP-1414S</a></li> <li><a href="/wiki/Cyprazepam" title="Cyprazepam">Cyprazepam</a></li> <li><a href="/wiki/Delorazepam" title="Delorazepam">Delorazepam</a></li> <li><a href="/wiki/Demoxepam" title="Demoxepam">Demoxepam</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diclazepam" title="Diclazepam">Diclazepam</a></li> <li><a href="/wiki/Dimdazenil" title="Dimdazenil">Dimdazenil</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Elfazepam" title="Elfazepam">Elfazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Ethyl_carfluzepate" title="Ethyl carfluzepate">Ethyl carfluzepate</a></li> <li><a href="/wiki/Ethyl_dirazepate" title="Ethyl dirazepate">Ethyl dirazepate</a></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/FG-8205" title="FG-8205">FG-8205</a></li> <li><a href="/wiki/Fletazepam" title="Fletazepam">Fletazepam</a></li> <li><a href="/wiki/Flubromazepam" title="Flubromazepam">Flubromazepam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutazolam" title="Flutazolam">Flutazolam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Fosazepam" title="Fosazepam">Fosazepam</a></li> <li><a href="/wiki/Gidazepam" title="Gidazepam">Gidazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Iclazepam" title="Iclazepam">Iclazepam</a></li> <li><a href="/wiki/Imidazenil" title="Imidazenil">Imidazenil</a></li> <li><a href="/wiki/Irazepine" title="Irazepine">Irazepine</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lofendazam" title="Lofendazam">Lofendazam</a></li> <li><a href="/wiki/Lopirazepam" title="Lopirazepam">Lopirazepam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Meclonazepam" title="Meclonazepam">Meclonazepam</a></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Menitrazepam" title="Menitrazepam">Menitrazepam</a></li> <li><a href="/wiki/Metaclazepam" title="Metaclazepam">Metaclazepam</a></li> <li><a href="/wiki/Mexazolam" title="Mexazolam">Mexazolam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Motrazepam" title="Motrazepam">Motrazepam</a></li> <li><a href="/wiki/N-Desalkylflurazepam" title="N-Desalkylflurazepam">N-Desalkylflurazepam</a></li> <li><a href="/wiki/Nifoxipam" title="Nifoxipam">Nifoxipam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazepate" title="Nitrazepate">Nitrazepate</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Nortetrazepam" title="Nortetrazepam">Nortetrazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Oxazolam" title="Oxazolam">Oxazolam</a></li> <li><a href="/wiki/Phenazepam" title="Phenazepam">Phenazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Pivoxazepam" title="Pivoxazepam">Pivoxazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a></li> <li><a href="/wiki/Premazepam" title="Premazepam">Premazepam</a></li> <li><a href="/wiki/Proflazepam" title="Proflazepam">Proflazepam</a></li> <li><a href="/wiki/Pyrazolam" title="Pyrazolam">Pyrazolam</a></li> <li><a href="/wiki/QH-II-66" title="QH-II-66">QH-II-66</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Reclazepam" title="Reclazepam">Reclazepam</a></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li> <li><a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a></li> <li><a href="/wiki/Ripazepam" title="Ripazepam">Ripazepam</a></li> <li><a href="/wiki/Ro48-6791" title="Ro48-6791">Ro48-6791</a></li> <li><a href="/wiki/Ro48-8684" title="Ro48-8684">Ro48-8684</a></li> <li><a href="/wiki/SH-053-R-CH3-2%E2%80%B2F" title="SH-053-R-CH3-2′F">SH-053-R-CH3-2′F</a></li> <li><a href="/wiki/Sulazepam" title="Sulazepam">Sulazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Tetrazepam" title="Tetrazepam">Tetrazepam</a></li> <li><a href="/wiki/Tolufazepam" class="mw-redirect" title="Tolufazepam">Tolufazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li> <li><a href="/wiki/Triflubazam" title="Triflubazam">Triflubazam</a></li> <li><a href="/wiki/Triflunordazepam" title="Triflunordazepam">Triflunordazepam (Ro5-2904)</a></li> <li><a href="/wiki/Tuclazepam" title="Tuclazepam">Tuclazepam</a></li> <li><a href="/wiki/Uldazepam" title="Uldazepam">Uldazepam</a></li> <li><a href="/wiki/Zapizolam" title="Zapizolam">Zapizolam</a></li> <li><a href="/wiki/Zolazepam" title="Zolazepam">Zolazepam</a></li> <li><a href="/wiki/Zomebazam" title="Zomebazam">Zomebazam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Clocental" title="Clocental">Clocental</a></li> <li><a href="/wiki/Cyclarbamate" title="Cyclarbamate">Cyclarbamate</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Emylcamate" title="Emylcamate">Emylcamate</a></li> <li><a href="/wiki/Ethinamate" title="Ethinamate">Ethinamate</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Hexapropymate" title="Hexapropymate">Hexapropymate</a></li> <li><a href="/wiki/Hydroxyphenamate" title="Hydroxyphenamate">Hydroxyphenamate</a></li> <li><a href="/wiki/Lorbamate" title="Lorbamate">Lorbamate</a></li> <li><a href="/wiki/Mebutamate" title="Mebutamate">Mebutamate</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/wiki/Nisobamate" title="Nisobamate">Nisobamate</a></li> <li><a href="/wiki/Pentabamate" title="Pentabamate">Pentabamate</a></li> <li><a href="/wiki/Phenprobamate" title="Phenprobamate">Phenprobamate</a></li> <li><a href="/wiki/Procymate" title="Procymate">Procymate</a></li> <li><a href="/wiki/Styramate" title="Styramate">Styramate</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tybamate" title="Tybamate">Tybamate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Methylapigenin" title="6-Methylapigenin">6-Methylapigenin</a></li> <li><a href="/wiki/Ampelopsin" title="Ampelopsin">Ampelopsin (dihydromyricetin)</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/wiki/Baicalin" title="Baicalin">Baicalin</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">EGC</a></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a></li> <li><a href="/wiki/Hispidulin" title="Hispidulin">Hispidulin</a></li> <li><a href="/w/index.php?title=Linarin&action=edit&redlink=1" class="new" title="Linarin (page does not exist)">Linarin</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=Trans-6,4%E2%80%B2-dimethoxyretrochalcone&action=edit&redlink=1" class="new" title="Trans-6,4′-dimethoxyretrochalcone (page does not exist)">Rc-OMe</a></li> <li><a href="/wiki/Scutellaria" title="Scutellaria">Skullcap</a> constituents (e.g., <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>)</li> <li><a href="/wiki/Wogonin" title="Wogonin">Wogonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Metomidate" title="Metomidate">Metomidate</a></li> <li><a href="/wiki/Propoxate" title="Propoxate">Propoxate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Kava" title="Kava">Kava</a> constituents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=10-Methoxyyangonin&action=edit&redlink=1" class="new" title="10-Methoxyyangonin (page does not exist)">10-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxyyangonin&action=edit&redlink=1" class="new" title="11-Methoxyyangonin (page does not exist)">11-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Hydroxyyangonin&action=edit&redlink=1" class="new" title="11-Hydroxyyangonin (page does not exist)">11-Hydroxyyangonin</a></li> <li><a href="/wiki/Desmethoxyyangonin" title="Desmethoxyyangonin">Desmethoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxy-12-hydroxydehydrokavain&action=edit&redlink=1" class="new" title="11-Methoxy-12-hydroxydehydrokavain (page does not exist)">11-Methoxy-12-hydroxydehydrokavain</a></li> <li><a href="/w/index.php?title=7,8-Dihydroyangonin&action=edit&redlink=1" class="new" title="7,8-Dihydroyangonin (page does not exist)">7,8-Dihydroyangonin</a></li> <li><a href="/wiki/Kavain" title="Kavain">Kavain</a></li> <li><a href="/w/index.php?title=5-Hydroxykavain&action=edit&redlink=1" class="new" title="5-Hydroxykavain (page does not exist)">5-Hydroxykavain</a></li> <li><a href="/w/index.php?title=5,6-Dihydroyangonin&action=edit&redlink=1" class="new" title="5,6-Dihydroyangonin (page does not exist)">5,6-Dihydroyangonin</a></li> <li><a href="/w/index.php?title=7,8-Dihydrokavain&action=edit&redlink=1" class="new" title="7,8-Dihydrokavain (page does not exist)">7,8-Dihydrokavain</a></li> <li><a href="/w/index.php?title=5,6,7,8-Tetrahydroyangonin&action=edit&redlink=1" class="new" title="5,6,7,8-Tetrahydroyangonin (page does not exist)">5,6,7,8-Tetrahydroyangonin</a></li> <li><a href="/w/index.php?title=5,6-Dehydromethysticin&action=edit&redlink=1" class="new" title="5,6-Dehydromethysticin (page does not exist)">5,6-Dehydromethysticin</a></li> <li><a href="/wiki/Methysticin" title="Methysticin">Methysticin</a></li> <li><a href="/w/index.php?title=7,8-Dihydromethysticin&action=edit&redlink=1" class="new" title="7,8-Dihydromethysticin (page does not exist)">7,8-Dihydromethysticin</a></li> <li><a href="/wiki/Yangonin" title="Yangonin">Yangonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Monoureide" class="mw-redirect" title="Monoureide">Monoureides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acecarbromal" title="Acecarbromal">Acecarbromal</a></li> <li><a href="/wiki/Apronal" title="Apronal">Apronal (apronalide)</a></li> <li><a href="/wiki/Bromisoval" title="Bromisoval">Bromisoval</a></li> <li><a href="/wiki/Carbromal" title="Carbromal">Carbromal</a></li> <li><a href="/w/index.php?title=Capuride&action=edit&redlink=1" class="new" title="Capuride (page does not exist)">Capuride</a></li> <li><a href="/w/index.php?title=Ectylurea&action=edit&redlink=1" class="new" title="Ectylurea (page does not exist)">Ectylurea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acebrochol" title="Acebrochol">Acebrochol</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/Androstenol" title="Androstenol">Androstenol</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li>Certain <a href="/wiki/Anabolic-androgenic_steroid" class="mw-redirect" title="Anabolic-androgenic steroid">anabolic-androgenic steroids</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-DHP</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-DHP</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-DHP</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">DHT</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li> <li><a href="/wiki/Minaxolone" title="Minaxolone">Minaxolone</a></li> <li><a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a></li> <li><a href="/wiki/ORG-21465" title="ORG-21465">ORG-21465</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Posovolone" title="Posovolone">Posovolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone (eltanolone)</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Renanolone" title="Renanolone">Renanolone</a></li> <li><a href="/w/index.php?title=SAGE-105&action=edit&redlink=1" class="new" title="SAGE-105 (page does not exist)">SAGE-105</a></li> <li><a href="/wiki/SAGE-324" title="SAGE-324">SAGE-324</a></li> <li><a href="/w/index.php?title=SAGE-516&action=edit&redlink=1" class="new" title="SAGE-516 (page does not exist)">SAGE-516</a></li> <li><a href="/w/index.php?title=SAGE-689&action=edit&redlink=1" class="new" title="SAGE-689 (page does not exist)">SAGE-689</a></li> <li><a href="/w/index.php?title=SAGE-872&action=edit&redlink=1" class="new" title="SAGE-872 (page does not exist)">SAGE-872</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li> <li><a href="/wiki/Zuranolone" title="Zuranolone">Zuranolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Cyclopyrrolone" class="mw-redirect" title="Cyclopyrrolone">Cyclopyrrolones</a></i>: <a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Pagoclone" title="Pagoclone">Pagoclone</a></li> <li><a href="/wiki/Pazinaclone" title="Pazinaclone">Pazinaclone</a></li> <li><a href="/wiki/Suproclone" title="Suproclone">Suproclone</a></li> <li><a href="/wiki/Suriclone" title="Suriclone">Suriclone</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> <ul><li><i><a href="/wiki/Imidazopyridine" title="Imidazopyridine">Imidazopyridines</a></i>: <a href="/wiki/Alpidem" title="Alpidem">Alpidem</a></li> <li><a href="/wiki/DS-1_(drug)" title="DS-1 (drug)">DS-1</a></li> <li><a href="/wiki/Necopidem" title="Necopidem">Necopidem</a></li> <li><a href="/wiki/Saripidem" title="Saripidem">Saripidem</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li></ul> <ul><li><i><a href="/wiki/Pyrazolopyrimidine" title="Pyrazolopyrimidine">Pyrazolopyrimidines</a></i>: <a href="/wiki/Divaplon" title="Divaplon">Divaplon</a></li> <li><a href="/wiki/Fasiplon" title="Fasiplon">Fasiplon</a></li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a></li> <li><a href="/wiki/Lorediplon" title="Lorediplon">Lorediplon</a></li> <li><a href="/wiki/Ocinaplon" title="Ocinaplon">Ocinaplon</a></li> <li><a href="/wiki/Panadiplon" title="Panadiplon">Panadiplon</a></li> <li><a href="/wiki/Taniplon" title="Taniplon">Taniplon</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/Adipiplon" title="Adipiplon">Adipiplon</a></li> <li><a href="/wiki/CGS-8216" title="CGS-8216">CGS-8216</a></li> <li><a href="/wiki/CGS-9896" title="CGS-9896">CGS-9896</a></li> <li><a href="/wiki/CGS-13767" title="CGS-13767">CGS-13767</a></li> <li><a href="/wiki/CGS-20625" title="CGS-20625">CGS-20625</a></li> <li><a href="/wiki/CL-218,872" title="CL-218,872">CL-218,872</a></li> <li><a href="/wiki/CP-615,003" title="CP-615,003">CP-615,003</a></li> <li><a href="/w/index.php?title=CTP-354&action=edit&redlink=1" class="new" title="CTP-354 (page does not exist)">CTP-354</a></li> <li><a href="/wiki/ELB-139" title="ELB-139">ELB-139</a></li> <li><a href="/wiki/GBLD-345" title="GBLD-345">GBLD-345</a></li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/JM-1232" title="JM-1232">JM-1232</a></li> <li><a href="/wiki/L-838,417" title="L-838,417">L-838,417</a></li> <li><a href="/wiki/Lirequinil" title="Lirequinil">Lirequinil (Ro41-3696)</a></li> <li><a href="/wiki/NS-2664" title="NS-2664">NS-2664</a></li> <li><a href="/wiki/NS-2710" title="NS-2710">NS-2710</a></li> <li><a href="/wiki/NS-11394" title="NS-11394">NS-11394</a></li> <li><a href="/wiki/Pipequaline" title="Pipequaline">Pipequaline</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/RWJ-51204" title="RWJ-51204">RWJ-51204</a></li> <li><a href="/wiki/SB-205,384" class="mw-redirect" title="SB-205,384">SB-205,384</a></li> <li><a href="/wiki/SX-3228" title="SX-3228">SX-3228</a></li> <li><a href="/w/index.php?title=TGSC01AA&action=edit&redlink=1" class="new" title="TGSC01AA (page does not exist)">TGSC01AA</a></li> <li><a href="/wiki/TP-003" title="TP-003">TP-003</a></li> <li><a href="/wiki/TPA-023" title="TPA-023">TPA-023</a></li> <li><a href="/wiki/TP-13" title="TP-13">TP-13</a></li> <li><a href="/wiki/U-89843A" title="U-89843A">U-89843A</a></li> <li><a href="/wiki/U-90042" title="U-90042">U-90042</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li> <li><a href="/wiki/Y-23684" title="Y-23684">Y-23684</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Phenol" title="Phenol">Phenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glutethimide" title="Glutethimide">Glutethimide</a></li> <li><a href="/wiki/Methyprylon" title="Methyprylon">Methyprylon</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Pyrithyldione" title="Pyrithyldione">Pyrithyldione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Pyrazolopyridine" class="mw-redirect" title="Pyrazolopyridine">Pyrazolopyridines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/ICI-190,622" title="ICI-190,622">ICI-190,622</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Afloqualone" title="Afloqualone">Afloqualone</a></li> <li><a href="/wiki/Cloroqualone" title="Cloroqualone">Cloroqualone</a></li> <li><a href="/wiki/Diproqualone" title="Diproqualone">Diproqualone</a></li> <li><a href="/wiki/Etaqualone" title="Etaqualone">Etaqualone</a></li> <li><a href="/wiki/Mebroqualone" title="Mebroqualone">Mebroqualone</a></li> <li><a href="/wiki/Mecloqualone" title="Mecloqualone">Mecloqualone</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Methylmethaqualone" title="Methylmethaqualone">Methylmethaqualone</a></li> <li><a href="/wiki/Nitromethaqualone" title="Nitromethaqualone">Nitromethaqualone</a></li> <li><a href="/wiki/SL-164" title="SL-164">SL-164</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles</a>/<a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">gases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Acetylglycinamide_chloral_hydrate" title="Acetylglycinamide chloral hydrate">Acetylglycinamide chloral hydrate</a></li> <li><a href="/wiki/Aliflurane" title="Aliflurane">Aliflurane</a></li> <li><a class="mw-selflink selflink">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Butylene" class="mw-redirect" title="Butylene">Butylene</a></li> <li><a href="/wiki/Centalun" title="Centalun">Centalun</a></li> <li><a href="/wiki/Chloral" title="Chloral">Chloral</a></li> <li><a href="/wiki/Chloral_betaine" title="Chloral betaine">Chloral betaine</a></li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li> <li><a href="/wiki/Cryofluorane" class="mw-redirect" title="Cryofluorane">Cryofluorane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dichloralphenazone" title="Dichloralphenazone">Dichloralphenazone</a></li> <li><a href="/wiki/Dichloromethane" title="Dichloromethane">Dichloromethane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Chloroethane" title="Chloroethane">Ethyl chloride</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Halopropane" title="Halopropane">Halopropane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosine</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norflurane" class="mw-redirect" title="Norflurane">Norflurane</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propylene</a></li> <li><a href="/wiki/Roflurane" title="Roflurane">Roflurane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Synthane" title="Synthane">Synthane</a></li> <li><a href="/wiki/Teflurane" title="Teflurane">Teflurane</a></li> <li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li> <li><a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">Trichloroethane (methyl chloroform)</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;">Others/unsorted</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Hydroxybutanal" title="3-Hydroxybutanal">3-Hydroxybutanal</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methylthiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methylthiobutyrolactone (page does not exist)">α-EMTBL</a></li> <li><a href="/w/index.php?title=AA-29504&action=edit&redlink=1" class="new" title="AA-29504 (page does not exist)">AA-29504</a></li> <li><a href="/wiki/Alogabat" title="Alogabat">Alogabat</a></li> <li><a href="/wiki/Avermectin" title="Avermectin">Avermectins</a> (e.g., <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds (e.g., <a href="/wiki/Lithium_bromide" title="Lithium bromide">lithium bromide</a>, <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Darigabat" title="Darigabat">Darigabat</a></li> <li><a href="/wiki/3,3-Diethyl-2-pyrrolidinone" title="3,3-Diethyl-2-pyrrolidinone">DEABL</a></li> <li><a href="/wiki/Deuterated_etifoxine" title="Deuterated etifoxine">Deuterated etifoxine</a></li> <li><a href="/wiki/Dihydroergoline" class="mw-redirect" title="Dihydroergoline">Dihydroergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">dihydroergosine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergoloid" title="Ergoloid">ergoloid (dihydroergotoxine)</a>)</li> <li><a href="/w/index.php?title=4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide&action=edit&redlink=1" class="new" title="4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide (page does not exist)">DS2</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li> <li><a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">Fenamates</a> (e.g., <a href="/wiki/Flufenamic_acid" title="Flufenamic acid">flufenamic acid</a>, <a href="/wiki/Mefenamic_acid" title="Mefenamic acid">mefenamic acid</a>, <a href="/wiki/Niflumic_acid" title="Niflumic acid">niflumic acid</a>, <a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">tolfenamic acid</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Hopantenic_acid" title="Hopantenic acid">Hopantenic acid</a></li> <li><a href="/wiki/KRM-II-81" title="KRM-II-81">KRM-II-81</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/4-O-methylhonokiol" class="mw-redirect" title="4-O-methylhonokiol">4-O-methylhonokiol</a>, <a href="/wiki/Honokiol" title="Honokiol">honokiol</a>, <a href="/wiki/Magnolol" title="Magnolol">magnolol</a>, <a href="/wiki/Obovatol" title="Obovatol">obovatol</a>)</li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Menthyl_isovalerate" title="Menthyl isovalerate">Menthyl isovalerate (validolum)</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</a></li> <li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Org_25435" class="mw-redirect" title="Org 25435">Org 25,435</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a></li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine (ezogabine)</a></li> <li><a href="/wiki/Safranal" title="Safranal">Safranal</a></li> <li><a href="/wiki/Seproxetine" title="Seproxetine">Seproxetine</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&action=edit&redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> (e.g., <a href="/wiki/Sulfonmethane" title="Sulfonmethane">sulfonmethane (sulfonal)</a>, <a href="/wiki/Tetronal" title="Tetronal">tetronal</a>, <a href="/wiki/Trional" title="Trional">trional</a>)</li> <li><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a> (e.g., <a href="/wiki/Borneol" title="Borneol">borneol</a>)</li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> constituents (e.g., <a href="/wiki/3-methylbutanoic_acid" class="mw-redirect" title="3-methylbutanoic acid">isovaleric acid</a>, <a href="/wiki/Isovaleramide" title="Isovaleramide">isovaleramide</a>, <a href="/wiki/Valerenic_acid" title="Valerenic acid">valerenic acid</a>, <a href="/w/index.php?title=Valerenol&action=edit&redlink=1" class="new" title="Valerenol (page does not exist)">valerenol</a>)</li></ul> <ul><li><i>Unsorted benzodiazepine site positive modulators:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/MRK-409_(MK-0343)" class="mw-redirect" title="MRK-409 (MK-0343)">MRK-409 (MK-0343)</a></li> <li><a href="/w/index.php?title=TCS-1105&action=edit&redlink=1" class="new" title="TCS-1105 (page does not exist)">TCS-1105</a></li> <li><a href="/wiki/TCS-1205" title="TCS-1205">TCS-1205</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> • <a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism/transport modulators</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Molecules_detected_in_outer_space800" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space800" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 1.5x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a class="mw-selflink selflink">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar 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title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a 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