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href="#Occurrence_and_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Occurrence and production</span> </div> </a> <ul id="toc-Occurrence_and_production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</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-Reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Reduction</span> </div> </a> <ul id="toc-Reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cycloadditions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cycloadditions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Cycloadditions</span> </div> </a> <ul id="toc-Cycloadditions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-With_electrophiles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#With_electrophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>With electrophiles</span> </div> </a> <ul id="toc-With_electrophiles-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</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-Niche" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Niche</span> </div> </a> <ul id="toc-Niche-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Derivatives</span> </div> </a> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Occurrence</span> </div> </a> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Toxicology</span> </div> </a> <ul id="toc-Toxicology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cited_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cited_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Cited sources</span> </div> </a> <ul id="toc-Cited_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</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 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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Anthracene</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 49 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-49" 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">49 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/Antraseen" title="Antraseen – Afrikaans" lang="af" hreflang="af" data-title="Antraseen" 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%A3%D9%86%D8%AB%D8%B1%D8%A7%D8%B3%D9%8A%D9%86" title="أنثراسين – Arabic" lang="ar" hreflang="ar" data-title="أنثراسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Antrasen" title="Antrasen – Azerbaijani" lang="az" hreflang="az" data-title="Antrasen" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D9%86%D8%AA%D8%B1%D8%A7%D8%B3%D9%86" title="آنتراسن – South Azerbaijani" lang="azb" hreflang="azb" data-title="آنتراسن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BD%D1%82%D1%80%D0%B0%D1%86%D1%8D%D0%BD" title="Антрацэн – Belarusian" lang="be" hreflang="be" data-title="Антрацэн" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Antrac%C3%A8" title="Antracè – Catalan" lang="ca" hreflang="ca" data-title="Antracè" 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/Antracen" title="Antracen – Czech" lang="cs" hreflang="cs" data-title="Antracen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Anthracen" title="Anthracen – German" lang="de" hreflang="de" data-title="Anthracen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BD%CE%B8%CF%81%CE%B1%CE%BA%CE%AD%CE%BD%CE%B9%CE%BF" title="Ανθρακένιο – Greek" lang="el" hreflang="el" data-title="Ανθρακένιο" 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/Antraceno" title="Antraceno – Spanish" lang="es" hreflang="es" data-title="Antraceno" 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/Antraceno" title="Antraceno – Esperanto" lang="eo" hreflang="eo" data-title="Antraceno" 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/Antrazeno" title="Antrazeno – Basque" lang="eu" hreflang="eu" data-title="Antrazeno" 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%A2%D9%86%D8%AA%D8%B1%D8%A7%D8%B3%D9%86" title="آنتراسن – Persian" lang="fa" hreflang="fa" data-title="آنتراسن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Anthrac%C3%A8ne" title="Anthracène – French" lang="fr" hreflang="fr" data-title="Anthracène" 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/Antraic%C3%A9in" title="Antraicéin – Irish" lang="ga" hreflang="ga" data-title="Antraicéin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%88%ED%8A%B8%EB%9D%BC%EC%84%BC" title="안트라센 – Korean" lang="ko" hreflang="ko" data-title="안트라센" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%B6%D5%BF%D6%80%D5%A1%D6%81%D5%A5%D5%B6" title="Անտրացեն – Armenian" lang="hy" hreflang="hy" data-title="Անտրացեն" 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%8F%E0%A4%A8%E0%A5%8D%E0%A4%A5%E0%A5%8D%E0%A4%B0%E0%A4%BE%E0%A4%B8%E0%A4%BF%E0%A4%A8" title="एन्थ्रासिन – Hindi" lang="hi" hreflang="hi" data-title="एन्थ्रासिन" 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/Antracen" title="Antracen – Croatian" lang="hr" hreflang="hr" data-title="Antracen" 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/Antrasena" title="Antrasena – Indonesian" lang="id" hreflang="id" data-title="Antrasena" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Antracene" title="Antracene – Italian" lang="it" hreflang="it" data-title="Antracene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%82%E0%B2%A5%E0%B3%8D%E0%B2%B0%E0%B2%B8%E0%B3%80%E0%B2%A8%E0%B3%8D" title="ಆಂಥ್ರಸೀನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಆಂಥ್ರಸೀನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BD%D1%82%D1%80%D0%B0%D1%86%D0%B5%D0%BD" title="Антрацен – Kazakh" lang="kk" hreflang="kk" data-title="Антрацен" 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%90%D0%BD%D1%82%D1%80%D0%B0%D1%86%D0%B5%D0%BD" title="Антрацен – Kyrgyz" lang="ky" hreflang="ky" data-title="Антрацен" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Antrac%C4%93ns" title="Antracēns – Latvian" lang="lv" hreflang="lv" data-title="Antracēns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Antrac%C3%A9n" title="Antracén – Hungarian" lang="hu" hreflang="hu" data-title="Antracén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Antraceen" title="Antraceen – Dutch" lang="nl" hreflang="nl" data-title="Antraceen" 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%82%A2%E3%83%B3%E3%83%88%E3%83%A9%E3%82%BB%E3%83%B3" title="アントラセン – Japanese" lang="ja" hreflang="ja" data-title="アントラセン" 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/Antracen" title="Antracen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Antracen" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Antratsen" title="Antratsen – Uzbek" lang="uz" hreflang="uz" data-title="Antratsen" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Antracen" title="Antracen – Polish" lang="pl" hreflang="pl" data-title="Antracen" 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/Antraceno" title="Antraceno – Portuguese" lang="pt" hreflang="pt" data-title="Antraceno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Antracen" title="Antracen – Romanian" lang="ro" hreflang="ro" data-title="Antracen" 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%90%D0%BD%D1%82%D1%80%D0%B0%D1%86%D0%B5%D0%BD" title="Антрацен – Russian" lang="ru" hreflang="ru" data-title="Антрацен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Antracina" title="Antracina – Sicilian" lang="scn" hreflang="scn" data-title="Antracina" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Antrac%C3%A9n" title="Antracén – Slovak" lang="sk" hreflang="sk" data-title="Antracén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Antracen" title="Antracen – Slovenian" lang="sl" hreflang="sl" data-title="Antracen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Antracen" title="Antracen – Serbian" lang="sr" hreflang="sr" data-title="Antracen" 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/Antracen" title="Antracen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Antracen" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Antraseeni" title="Antraseeni – Finnish" lang="fi" hreflang="fi" data-title="Antraseeni" 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/Antracen" title="Antracen – Swedish" lang="sv" hreflang="sv" data-title="Antracen" 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%86%E0%AE%A8%E0%AF%8D%E0%AE%A4%E0%AE%BF%E0%AE%B0%E0%AE%9A%E0%AF%80%E0%AE%A9%E0%AF%8D" title="ஆந்திரசீன் – Tamil" lang="ta" hreflang="ta" data-title="ஆந்திரசீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%99%E0%B8%97%E0%B8%A3%E0%B8%B2%E0%B8%8B%E0%B8%B5%E0%B8%99" title="แอนทราซีน – Thai" 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#b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Lead_too_short plainlinks metadata ambox ambox-content ambox-lead_too_short" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/40px-Wiki_letter_w.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/60px-Wiki_letter_w.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/80px-Wiki_letter_w.svg.png 2x" data-file-width="44" data-file-height="44" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article's <a href="/wiki/Wikipedia:Manual_of_Style/Lead_section#Length" title="Wikipedia:Manual of Style/Lead section">lead section</a> <b>may be too short to adequately <a href="/wiki/Wikipedia:Summary_style" title="Wikipedia:Summary style">summarize</a> the key points</b>.<span class="hide-when-compact"> Please consider expanding the lead to <a href="/wiki/Wikipedia:Manual_of_Style/Lead_section#Provide_an_accessible_overview" title="Wikipedia:Manual of Style/Lead section">provide an accessible overview</a> of all important aspects of the article.</span> <span class="date-container"><i>(<span class="date">April 2023</span>)</i></span></div></td></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r1084375498">.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%}</style> <table class="infobox ib-chembox"> <caption>Anthracene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Anthracene-numbering.svg" class="mw-file-description" title="Skeletal formula and numbering system of anthracene"><img alt="Skeletal formula and numbering system of anthracene" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Anthracene-numbering.svg/220px-Anthracene-numbering.svg.png" decoding="async" width="220" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Anthracene-numbering.svg/330px-Anthracene-numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Anthracene-numbering.svg/440px-Anthracene-numbering.svg.png 2x" data-file-width="834" data-file-height="398" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Anthracene_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the anthracene molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Anthracene_molecule_ball.png/220px-Anthracene_molecule_ball.png" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Anthracene_molecule_ball.png/330px-Anthracene_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Anthracene_molecule_ball.png/440px-Anthracene_molecule_ball.png 2x" data-file-width="2000" data-file-height="1185" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Anthracene.jpg" class="mw-file-description" title="Anthracene"><img alt="Anthracene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Anthracene.jpg/220px-Anthracene.jpg" decoding="async" width="220" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Anthracene.jpg/330px-Anthracene.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Anthracene.jpg/440px-Anthracene.jpg 2x" data-file-width="2976" data-file-height="3968" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Anthracene</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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=120-12-7">120-12-7</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=c1ccc2cc3ccccc3cc2c1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1905429 </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=35298">CHEBI:35298</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/chembldb/index.php/compound/inspect/ChEMBL333179">ChEMBL333179</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.8111.html">8111</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/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB07372">DB07372</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/100.003.974">100.003.974</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422152#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>217-004-5</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>67837 </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/C14315">C14315</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/8418">8418</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>CA9350000</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/EH46A1TLD7">EH46A1TLD7</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/DTXSID0023878">DTXSID0023878</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422152#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; background:transparent;"><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/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H<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: MWPLVEDNUUSJAV-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><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=1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MWPLVEDNUUSJAV-UHFFFAOYAK</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; background:transparent;"><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%;">c1ccc2cc3ccccc3cc2c1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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>14</sub><span title="Hydrogen">H</span><sub>10</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="7002178234000000000♠"></span>178.234</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Weak aromatic </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.28 g/cm<sup>3</sup> (25 °C)<sup id="cite_ref-crc1_1-0" class="reference"><a href="#cite_note-crc1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br /> 0.969 g/cm<sup>3</sup> (220 °C) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>216 °C (421 °F; 489 K)<sup id="cite_ref-crc1_1-2" class="reference"><a href="#cite_note-crc1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> at 760 mmHg </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>341.3 °C (646.3 °F; 614.5 K)<sup id="cite_ref-crc1_1-3" class="reference"><a href="#cite_note-crc1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> at 760 mmHg </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>0.022 mg/L (0 °C)<br /> 0.044 mg/L (25 °C)<br /> 0.29 mg/L (50 °C)<br /> 0.00045% w/w (100 °C, 3.9 MPa)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<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/Ethanol" title="Ethanol">alcohol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>O</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Benzene" title="Benzene">C<sub>6</sub>H<sub>6</sub></a>, <a href="/wiki/Chloroform" title="Chloroform">CHCl<sub>3</sub></a>,<sup id="cite_ref-crc1_1-1" class="reference"><a href="#cite_note-crc1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a><sup id="cite_ref-sioc_3-0" class="reference"><a href="#cite_note-sioc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> </td> <td>0.76 g/kg (16 °C)<br /> 19 g/kg (19.5 °C)<br /> 3.28 g/kg (25 °C)<sup id="cite_ref-sioc_3-1" class="reference"><a href="#cite_note-sioc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Methanol" title="Methanol">methanol</a> </td> <td>18 g/kg (19.5 °C)<sup id="cite_ref-sioc_3-2" class="reference"><a href="#cite_note-sioc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Hexane" title="Hexane">hexane</a> </td> <td>3.7 g/kg<sup id="cite_ref-sioc_3-3" class="reference"><a href="#cite_note-sioc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Toluene" title="Toluene">toluene</a> </td> <td>9.2 g/kg (16.5 °C)<br /> 129.4 g/kg (100 °C)<sup id="cite_ref-sioc_3-4" class="reference"><a href="#cite_note-sioc-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a> </td> <td>7.32 g/kg<sup id="cite_ref-sioc_3-5" class="reference"><a href="#cite_note-sioc-3"><span class="cite-bracket">[</span>3<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>4.56 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>0.01 kPa (125.9 °C)<br /> 0.1 kPa (151.5 °C)<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><br /> 13.4 kPa (250 °C)<sup id="cite_ref-nist_5-0" class="reference"><a href="#cite_note-nist-5"><span class="cite-bracket">[</span>5<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/Henry%27s_law" title="Henry's law">Henry's law<br />constant</a> (<i>k</i><sub>H</sub>)</div> </td> <td>0.0396 L·atm/mol<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<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>345.6 nm, 363.2 nm<sup id="cite_ref-nist_5-1" class="reference"><a href="#cite_note-nist-5"><span class="cite-bracket">[</span>5<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/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−129.8<span style="margin:0 .15em 0 .25em">×</span>10<sup>−6</sup> cm<sup>3</sup>/mol<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Thermal_conductivity" class="mw-redirect" title="Thermal conductivity">Thermal conductivity</a> </td> <td>0.1416 W/(m·K) (240 °C)<br /> 0.1334 W/(m·K) (270 °C)<br /> 0.1259 W/(m·K) (300 °C)<sup id="cite_ref-wileyfr_8-0" class="reference"><a href="#cite_note-wileyfr-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.602 cP (240 °C)<br /> 0.498 cP (270 °C)<br /> 0.429 cP (300 °C)<sup id="cite_ref-wileyfr_8-1" class="reference"><a href="#cite_note-wileyfr-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td><a href="/wiki/Monoclinic_crystal_system" title="Monoclinic crystal system">Monoclinic</a> (290 K)<sup id="cite_ref-sccs_9-0" class="reference"><a href="#cite_note-sccs-9"><span class="cite-bracket">[</span>9<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/Space_group" title="Space group">Space group</a></div> </td> <td>P2<sub>1</sub>/b<sup id="cite_ref-sccs_9-1" class="reference"><a href="#cite_note-sccs-9"><span class="cite-bracket">[</span>9<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/Molecular_symmetry" title="Molecular symmetry">Point group</a></div> </td> <td>D<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2h</sub></span></span><sup id="cite_ref-sccs_9-2" class="reference"><a href="#cite_note-sccs-9"><span class="cite-bracket">[</span>9<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/Lattice_constant" title="Lattice constant">Lattice constant</a></div> </td> <td><div><i>a</i> = 8.562 Å, <i>b</i> = 6.038 Å, <i>c</i> = 11.184 Å<sup id="cite_ref-sccs_9-3" class="reference"><a href="#cite_note-sccs-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></div><div>α = 90°, β = 124.7°, γ = 90°</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </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>210.5 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>207.5 J/(mol·K) </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>129.2 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>7061 kJ/mol<sup id="cite_ref-nist_5-2" class="reference"><a href="#cite_note-nist-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><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-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-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_11-0" class="reference"><a href="#cite_note-sigma-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/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>Warning</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="H302: Harmful if swallowed">H302</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="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr><sup id="cite_ref-sigma_11-1" class="reference"><a href="#cite_note-sigma-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/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</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="P501: Dispose of contents/container to ...">P501</abbr><sup id="cite_ref-sigma_11-2" class="reference"><a href="#cite_note-sigma-11"><span class="cite-bracket">[</span>11<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-74-diamond-refs"><sup id="cite_ref-fca_12-0" class="reference"><a href="#cite_note-fca-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></div><div class="nfpa-704-diamond-container nfpa-704-diamond-container-ref"><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_811dcee2cbfc5fb2" /></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><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 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</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>121 °C (250 °F; 394 K)<sup id="cite_ref-sigma_11-3" class="reference"><a href="#cite_note-sigma-11"><span class="cite-bracket">[</span>11<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/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>540 °C (1,004 °F; 813 K)<sup id="cite_ref-sigma_11-4" class="reference"><a href="#cite_note-sigma-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><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>100-149 mg/kg (rats, oral) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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=464364595&page2=Anthracene">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>Anthracene</b> is a solid <a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">polycyclic aromatic hydrocarbon</a> (PAH) of formula C<sub>14</sub>H<sub>10</sub>, consisting of three fused <a href="/wiki/Benzene" title="Benzene">benzene</a> rings. It is a component of <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>. Anthracene is used in the <a href="/wiki/Economic_production" class="mw-redirect" title="Economic production">production</a> of the red <a href="/wiki/Dye" title="Dye">dye</a> <a href="/wiki/Alizarin" title="Alizarin">alizarin</a> and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) <a href="/wiki/Fluorescence" title="Fluorescence">fluorescence</a> under <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> radiation.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History_and_etymology">History and etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=1" title="Edit section: History and etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Crude anthracene (with a melting point of only 180°) was discovered in 1832 by <a href="/wiki/Jean-Baptiste_Dumas" title="Jean-Baptiste Dumas">Jean-Baptiste Dumas</a> and <a href="/wiki/Auguste_Laurent" title="Auguste Laurent">Auguste Laurent</a><sup id="cite_ref-:0_14-0" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>, Laurent called it <i>paranaphtaline</i> in his 1835 publication of the discovery,<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> which is translated to English as <b>paranaphthalene</b>.<sup id="cite_ref-:0_14-1" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Two years later, however, he decided to rename the compound to its modern name derived from <a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Ancient Greek</a>: <span lang="grc">ἄνθραξ</span>, <small><a href="/wiki/Romanization_of_Ancient_Greek" class="mw-redirect" title="Romanization of Ancient Greek">romanized</a>: </small><span title="Ancient Greek-language romanization"><i lang="grc-Latn">anthrax</i></span>, <small><a href="/wiki/Literal_translation" title="Literal translation">lit.</a> </small>'coal' because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene.<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> This notion was disproved in 1850s and 1860s.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><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> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence_and_production">Occurrence and production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=2" title="Edit section: Occurrence and production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coal tar, which contains around 1.5% anthracene, remains a major source of this material. Common impurities are <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> and <a href="/wiki/Carbazole" title="Carbazole">carbazole</a>. The mineral form of anthracene is called freitalite and is related to a coal deposit.<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> A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called <a href="/wiki/Elbs_reaction" title="Elbs reaction">Elbs reaction</a>, for example from <i>o</i>-tolyl phenyl ketone.<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> </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=Anthracene&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=4" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M<sup>+</sup>[anthracene]<sup>−</sup> (M = Li, Na, K). Hydrogenation gives 9,10-<a href="/wiki/Dihydroanthracene" class="mw-redirect" title="Dihydroanthracene">dihydroanthracene</a>, preserving the aromaticity of the two flanking rings.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Cycloadditions">Cycloadditions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=5" title="Edit section: Cycloadditions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In any solvent except water,<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> anthracene <a href="/wiki/Photochemistry" title="Photochemistry">photodimerizes</a> by the action of <a href="/wiki/Ultraviolet" title="Ultraviolet">UV</a> light: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Anthracene_Photodimerisation.svg" class="mw-file-description" title="Anthracene dimer"><img alt="Anthracene dimer" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Anthracene_Photodimerisation.svg/360px-Anthracene_Photodimerisation.svg.png" decoding="async" width="360" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Anthracene_Photodimerisation.svg/540px-Anthracene_Photodimerisation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Anthracene_Photodimerisation.svg/720px-Anthracene_Photodimerisation.svg.png 2x" data-file-width="430" data-file-height="165" /></a></span></dd></dl> <p>The <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimer</a>, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a>. It reverts to anthracene thermally or with <a href="/wiki/Ultraviolet" title="Ultraviolet">UV</a> irradiation below 300 nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>.<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> </p><p>Anthracene also reacts with dienophile <a href="/wiki/Singlet_oxygen" title="Singlet oxygen">singlet oxygen</a> in a [4+2]-cycloaddition (<a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a>): </p> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:Anthracene_singlet_oxygen_Diels-Alder_reaction.svg" class="mw-file-description" title="Diels alder reaction of anthracene with singlet oxygen"><img alt="Diels alder reaction of anthracene with singlet oxygen" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Anthracene_singlet_oxygen_Diels-Alder_reaction.svg/360px-Anthracene_singlet_oxygen_Diels-Alder_reaction.svg.png" decoding="async" width="360" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Anthracene_singlet_oxygen_Diels-Alder_reaction.svg/540px-Anthracene_singlet_oxygen_Diels-Alder_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Anthracene_singlet_oxygen_Diels-Alder_reaction.svg/720px-Anthracene_singlet_oxygen_Diels-Alder_reaction.svg.png 2x" data-file-width="1039" data-file-height="261" /></a><figcaption>Diels alder reaction of anthracene with singlet oxygen</figcaption></figure></dd></dl> <div class="mw-heading mw-heading3"><h3 id="With_electrophiles">With electrophiles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=6" title="Edit section: With electrophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chemical <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> occurs readily, giving <a href="/wiki/Anthraquinone" title="Anthraquinone">anthraquinone</a>, C<sub>14</sub>H<sub>8</sub>O<sub>2</sub> (below), for example using <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> and <a href="/wiki/Vanadyl_acetylacetonate" title="Vanadyl acetylacetonate">vanadyl acetylacetonate</a>.<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> </p> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:Anthraquinone_acsv.svg" class="mw-file-description" title="Anthraquione"><img alt="Anthraquione" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Anthraquinone_acsv.svg/120px-Anthraquinone_acsv.svg.png" decoding="async" width="120" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Anthraquinone_acsv.svg/180px-Anthraquinone_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Anthraquinone_acsv.svg/240px-Anthraquinone_acsv.svg.png 2x" data-file-width="857" data-file-height="749" /></a><figcaption>Anthraquione</figcaption></figure></dd></dl> <p>Electrophilic substitution of anthracene occurs at the 9 position. For example, formylation affords <a href="/wiki/9-Anthracenecarboxaldehyde" class="mw-redirect" title="9-Anthracenecarboxaldehyde">9-anthracenecarboxaldehyde</a>. Substitution at other positions is effected indirectly, for example starting with anthroquinone.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Bromination of anthracene gives 9,10-dibromoanthracene.<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> </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=Anthracene&action=edit&section=7" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anthracene is converted mainly to <a href="/wiki/Anthraquinone" title="Anthraquinone">anthraquinone</a>, a precursor to dyes.<sup id="cite_ref-Ullmann_28-0" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Niche">Niche</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=8" title="Edit section: Niche"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anthracene, a wide band-gap <a href="/wiki/Organic_semiconductor" title="Organic semiconductor">organic semiconductor</a> is used as a <a href="/wiki/Scintillator" title="Scintillator">scintillator</a> for detectors of high-energy <a href="/wiki/Photon" title="Photon">photons</a>, <a href="/wiki/Electron" title="Electron">electrons</a> and <a href="/wiki/Alpha_particle" title="Alpha particle">alpha particles</a>. Plastics, such as <a href="/wiki/Polyvinyltoluene" class="mw-redirect" title="Polyvinyltoluene">polyvinyltoluene</a>, can be doped with anthracene to produce a plastic <a href="/wiki/Scintillator" title="Scintillator">scintillator</a> that is approximately water-equivalent for use in <a href="/wiki/Radiation_therapy" title="Radiation therapy">radiation therapy</a> <a href="/wiki/Dosimetry" title="Dosimetry">dosimetry</a>. Anthracene's <a href="/wiki/Emission_spectrum" title="Emission spectrum">emission spectrum</a> peaks at between 400 nm and 440 nm. </p><p>It is also used in <a href="/wiki/Wood" title="Wood">wood</a> <a href="/wiki/Preservative" title="Preservative">preservatives</a>, <a href="/wiki/Insecticide" title="Insecticide">insecticides</a>, and coating <a href="/wiki/Commodity" title="Commodity">materials</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2010)">citation needed</span></a></i>]</sup> </p><p>Anthracene is commonly used as a UV tracer in conformal coatings applied to printed wiring boards. The anthracene tracer allows the conformal coating to be inspected under UV light.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Fluorescence_of_Anthracene_under_UV_light.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Fluorescence_of_Anthracene_under_UV_light.jpg/220px-Fluorescence_of_Anthracene_under_UV_light.jpg" decoding="async" width="220" height="222" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Fluorescence_of_Anthracene_under_UV_light.jpg/330px-Fluorescence_of_Anthracene_under_UV_light.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Fluorescence_of_Anthracene_under_UV_light.jpg/440px-Fluorescence_of_Anthracene_under_UV_light.jpg 2x" data-file-width="2822" data-file-height="2845" /></a><figcaption>Fluorescence of anthracene under UV light</figcaption></figure><div style="clear:left;" class=""></div></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Derivatives">Derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=9" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Antracene_diradical_AFM2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Antracene_diradical_AFM2.png/220px-Antracene_diradical_AFM2.png" decoding="async" width="220" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Antracene_diradical_AFM2.png/330px-Antracene_diradical_AFM2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Antracene_diradical_AFM2.png/440px-Antracene_diradical_AFM2.png 2x" data-file-width="483" data-file-height="344" /></a><figcaption>False-color <a href="/wiki/Atomic_force_microscopy" title="Atomic force microscopy">AFM</a> image of anthracene diradical, where hydrogen atoms are removed at carbons 9 and 10</figcaption></figure> <p>A variety of anthracene derivatives find specialized uses. Derivatives having a <a href="/wiki/Hydroxide" title="Hydroxide">hydroxyl group</a> are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to <a href="/wiki/Phenol" title="Phenol">phenol</a> and <a href="/wiki/Naphthol_(disambiguation)" class="mw-redirect" title="Naphthol (disambiguation)">naphthols</a>, and hydroxyanthracene (also called anthrol, and anthracenol)<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> are <a href="/wiki/Pharmacology" title="Pharmacology">pharmacologically</a> active. Anthracene may also be found with multiple hydroxyl groups, as in <a href="/wiki/9,10-dihydroxyanthracene" class="mw-redirect" title="9,10-dihydroxyanthracene">9,10-dihydroxyanthracene</a>. </p><p>Some anthracene derivatives are used as pharmaceutical drugs, including <a href="/wiki/Bisantrene" title="Bisantrene">bisantrene</a>, <a href="/w/index.php?title=Trazitiline&action=edit&redlink=1" class="new" title="Trazitiline (page does not exist)">trazitiline</a>, and <a href="/wiki/Benzoctamine" title="Benzoctamine">benzoctamine</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=10" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anthracene, as many other <a href="/wiki/Polycyclic_aromatic_hydrocarbons" class="mw-redirect" title="Polycyclic aromatic hydrocarbons">polycyclic aromatic hydrocarbons</a>, is generated during combustion processes. Exposure to humans happens mainly through tobacco smoke and ingestion of food contaminated with combustion products. </p> <div class="mw-heading mw-heading2"><h2 id="Toxicology">Toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=11" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many investigations indicate that anthracene is noncarcinogenic: "consistently negative findings in numerous in vitro and in vivo genotoxicity tests". Early experiments suggested otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbons. Furthermore, it is readily biodegraded in soil. It is especially susceptible to degradation in the presence of light.<sup id="cite_ref-Ullmann_28-1" class="reference"><a href="#cite_note-Ullmann-28"><span class="cite-bracket">[</span>28<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=Anthracene&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/9,10-Dithioanthracene" title="9,10-Dithioanthracene">9,10-Dithioanthracene</a>, derivative with two thiol groups added to the central ring</li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li></ul> <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=Anthracene&action=edit&section=13" title="Edit section: References"><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 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href="#cite_ref-sioc_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-sioc_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-sioc_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-sioc_3-5"><sup><i><b>f</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="CITEREFSeidellLinke1919" class="citation book cs1">Seidell, Atherton; Linke, William F. (1919). <a rel="nofollow" class="external text" href="https://archive.org/details/solubilitiesino01seidgoog"><i>Solubilities of Inorganic and Organic Compounds</i></a> (2nd ed.). New York: D. Van Nostrand Company. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/solubilitiesino01seidgoog/page/n111">81</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Solubilities+of+Inorganic+and+Organic+Compounds&rft.place=New+York&rft.pages=81&rft.edition=2nd&rft.pub=D.+Van+Nostrand+Company&rft.date=1919&rft.aulast=Seidell&rft.aufirst=Atherton&rft.au=Linke%2C+William+F.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fsolubilitiesino01seidgoog&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" 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">Haynes, p. 6.116</span> </li> <li id="cite_note-nist-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-nist_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nist_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-nist_5-2"><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=C120127&Mask=FFFF&Units=SI">Anthracene</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) </span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text">Haynes, p. 5.157</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Haynes, p. 3.579</span> </li> <li id="cite_note-wileyfr-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-wileyfr_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-wileyfr_8-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141101132638/http://www.infotherm.com/static/molpages/02/32/mol23245.html">"Properties of Anthracene"</a>. <i>www.infotherm.com</i>. Wiley Information Services GmbH. Archived from <a rel="nofollow" class="external text" href="http://www.infotherm.com/static/molpages/02/32/mol23245.html">the original</a> on 2014-11-01<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-06-22</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.infotherm.com&rft.atitle=Properties+of+Anthracene&rft_id=http%3A%2F%2Fwww.infotherm.com%2Fstatic%2Fmolpages%2F02%2F32%2Fmol23245.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></span> </li> <li id="cite_note-sccs-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-sccs_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sccs_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sccs_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-sccs_9-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDouglasHo2007" class="citation book cs1">Douglas, Bodie E.; Ho, Shih-Ming (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=hYRCAAAAQBAJ&pg=PA289"><i>Structure and Chemistry of Crystalline Solids</i></a>. New York: Springer Science+Business Media, Inc. p. 289. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-26147-8" title="Special:BookSources/978-0-387-26147-8"><bdi>978-0-387-26147-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Structure+and+Chemistry+of+Crystalline+Solids&rft.place=New+York&rft.pages=289&rft.pub=Springer+Science%2BBusiness+Media%2C+Inc.&rft.date=2007&rft.isbn=978-0-387-26147-8&rft.aulast=Douglas&rft.aufirst=Bodie+E.&rft.au=Ho%2C+Shih-Ming&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DhYRCAAAAQBAJ%26pg%3DPA289&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">Haynes, p. 5.41</span> </li> <li id="cite_note-sigma-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sigma_11-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-sigma_11-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-sigma_11-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich Co.</a>, <a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/aldrich/141062">Anthracene</a>. </span> </li> <li id="cite_note-fca-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-fca_12-0">^</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.fishersci.ca/viewmsds.do?catNo=AC104860050">"MSDS of Anthracene"</a>. <i>www.fishersci.ca</i>. Fisher Scientific<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-06-22</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.fishersci.ca&rft.atitle=MSDS+of+Anthracene&rft_id=https%3A%2F%2Fwww.fishersci.ca%2Fviewmsds.do%3FcatNo%3DAC104860050&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></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 id="CITEREFLindsey" class="citation web cs1">Lindsey, Jonathan; et al. <a rel="nofollow" class="external text" href="http://omlc.ogi.edu/spectra/PhotochemCAD/html/022.html">"Anthracene"</a>. <i>PhotochemCAD</i><span class="reference-accessdate">. Retrieved <span class="nowrap">20 February</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PhotochemCAD&rft.atitle=Anthracene&rft.aulast=Lindsey&rft.aufirst=Jonathan&rft_id=http%3A%2F%2Fomlc.ogi.edu%2Fspectra%2FPhotochemCAD%2Fhtml%2F022.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></span> </li> <li id="cite_note-:0-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_14-1"><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="CITEREFWisniak2009" class="citation journal cs1">Wisniak, Jaime (2009). <a rel="nofollow" class="external text" href="https://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0187-893X2009000200010">"Auguste Laurent: Radical and radicals"</a>. <i>Educación química</i>. <b>20</b> (2): 166–175. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0187-893X">0187-893X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Educaci%C3%B3n+qu%C3%ADmica&rft.atitle=Auguste+Laurent%3A+Radical+and+radicals&rft.volume=20&rft.issue=2&rft.pages=166-175&rft.date=2009&rft.issn=0187-893X&rft.aulast=Wisniak&rft.aufirst=Jaime&rft_id=https%3A%2F%2Fwww.scielo.org.mx%2Fscielo.php%3Fscript%3Dsci_arttext%26pid%3DS0187-893X2009000200010&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged November 2024">dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></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 class="citation cs1"><span class="cs1-ws-icon" title="s:fr:Comptes rendus de l'Académie des sciences/Tome 1, 1835/7 décembre"><a class="external text" href="https://en.wikisource.org/wiki/fr:Comptes_rendus_de_l%27Acad%C3%A9mie_des_sciences/Tome_1,_1835/7_d%C3%A9cembre"><i>fr:Comptes rendus de l'Académie des sciences/Tome 1, 1835/7 décembre</i> </a></span> – via <a href="/wiki/Wikisource" title="Wikisource">Wikisource</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=fr%3AComptes+rendus+de+l%27Acad%C3%A9mie+des+sciences%2FTome+1%2C+1835%2F7+d%C3%A9cembre&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1 cs1-prop-foreign-lang-source"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=wZg5AAAAcAAJ&pg=PA149"><i>Annales de chimie et de physique</i></a> (in French). 1837.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Annales+de+chimie+et+de+physique&rft.date=1837&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwZg5AAAAcAAJ%26pg%3DPA149&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1 cs1-prop-foreign-lang-source"><a rel="nofollow" class="external text" href="https://new.societechimiquedefrance.fr/numero/a-propos-de-lanthracene-et-de-lalizarine-p3-n467">"À propos de l'anthracène et de l'alizarine - p3 - N°467 - L'Actualité Chimique, le journal de la SCF"</a>. <i>Société Chimique de France (SCF)</i> (in French)<span class="reference-accessdate">. Retrieved <span class="nowrap">2024-11-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Soci%C3%A9t%C3%A9+Chimique+de+France+%28SCF%29&rft.atitle=%C3%80+propos+de+l%27anthrac%C3%A8ne+et+de+l%27alizarine+-+p3+-+N%C2%B0467+-+L%27Actualit%C3%A9+Chimique%2C+le+journal+de+la+SCF&rft_id=https%3A%2F%2Fnew.societechimiquedefrance.fr%2Fnumero%2Fa-propos-de-lanthracene-et-de-lalizarine-p3-n467&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" 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="CITEREFJacksonWhite1880" class="citation journal cs1">Jackson, C. Loring; White, J. Fleming (1880). <a rel="nofollow" class="external text" href="https://www.jstor.org/stable/25138602">"Researches on the Substituted Benzyl Compounds. Ninth Paper. The Synthesis of Anthracene and Phenanthrene from Orthobrombenzylbromide"</a>. <i>Proceedings of the American Academy of Arts and Sciences</i>. <b>16</b>: 63–77. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2307%2F25138602">10.2307/25138602</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0199-9818">0199-9818</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+American+Academy+of+Arts+and+Sciences&rft.atitle=Researches+on+the+Substituted+Benzyl+Compounds.+Ninth+Paper.+The+Synthesis+of+Anthracene+and+Phenanthrene+from+Orthobrombenzylbromide&rft.volume=16&rft.pages=63-77&rft.date=1880&rft_id=info%3Adoi%2F10.2307%2F25138602&rft.issn=0199-9818&rft.aulast=Jackson&rft.aufirst=C.+Loring&rft.au=White%2C+J.+Fleming&rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F25138602&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></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">Freitalite, Mindat, <a rel="nofollow" class="external free" href="https://www.mindat.org/min-54360.html">https://www.mindat.org/min-54360.html</a></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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/anthracene.html">"Anthracene"</a>. <i>American Chemical Society</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2022-09-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=American+Chemical+Society&rft.atitle=Anthracene&rft_id=https%3A%2F%2Fwww.acs.org%2Fcontent%2Facs%2Fen%2Fmolecule-of-the-week%2Farchive%2Fa%2Fanthracene.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBass1962" class="citation journal cs1">Bass, K. C. (1962). "9,10-Dihydroanthracene". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>42</b>: 48. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.042.0048">10.15227/orgsyn.042.0048</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=9%2C10-Dihydroanthracene&rft.volume=42&rft.pages=48&rft.date=1962&rft_id=info%3Adoi%2F10.15227%2Forgsyn.042.0048&rft.aulast=Bass&rft.aufirst=K.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span>.</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="CITEREFJohnsonPagni" class="citation cs2">Johnson, Keith E.; Pagni, Richard M., "Liquid salts for reactions", <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>, New York: John Wiley, p. 28, <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%2F0471238961.liqupagn.a01">10.1002/0471238961.liqupagn.a01</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471238966" title="Special:BookSources/9780471238966"><bdi>9780471238966</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Liquid+salts+for+reactions&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.place=New+York&rft.pages=28&rft.pub=John+Wiley&rft_id=info%3Adoi%2F10.1002%2F0471238961.liqupagn.a01&rft.isbn=9780471238966&rft.aulast=Johnson&rft.aufirst=Keith+E.&rft.au=Pagni%2C+Richard+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" 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="CITEREFRickborn,_Bruce1998" class="citation book cs1">Rickborn, Bruce (1998). "The Retro– <SCP>D</SCP> iels– <SCP>A</SCP> lder Reaction Part <SCP>I</SCP> . <SCP>C</SCP>  <SCP>C</SCP> Dienophiles". <i>Organic Reactions</i>. pp. 1–393. <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%2F0471264180.or052.01">10.1002/0471264180.or052.01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-26418-7" title="Special:BookSources/978-0-471-26418-7"><bdi>978-0-471-26418-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Retro%E2%80%93+%3CSCP%3ED%3C%2FSCP%3E+iels%E2%80%93+%3CSCP%3EA%3C%2FSCP%3E+lder+Reaction+Part+%3CSCP%3EI%3C%2FSCP%3E+.+%3CSCP%3EC%3C%2FSCP%3E+%EF%A3%BF+%3CSCP%3EC%3C%2FSCP%3E+Dienophiles&rft.btitle=Organic+Reactions&rft.pages=1-393&rft.date=1998&rft_id=info%3Adoi%2F10.1002%2F0471264180.or052.01&rft.isbn=978-0-471-26418-7&rft.au=Rickborn%2C+Bruce&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBouas-Laurent,_HenriDesvergne,_Jean-PierreCastellan,_AlainLapouyade,_Rene2000" class="citation journal cs1">Bouas-Laurent, Henri; Desvergne, Jean-Pierre; Castellan, Alain; Lapouyade, Rene (2000). "Photodimerization of anthracenes in fluid solution: Structural aspects". <i>Chemical Society Reviews</i>. <b>29</b>: 43–55. <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%2Fa801821i">10.1039/a801821i</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Society+Reviews&rft.atitle=Photodimerization+of+anthracenes+in+fluid+solution%3A+Structural+aspects&rft.volume=29&rft.pages=43-55&rft.date=2000&rft_id=info%3Adoi%2F10.1039%2Fa801821i&rft.au=Bouas-Laurent%2C+Henri&rft.au=Desvergne%2C+Jean-Pierre&rft.au=Castellan%2C+Alain&rft.au=Lapouyade%2C+Rene&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></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="CITEREFCharletonProkopchuk2011" class="citation journal cs1">Charleton, Kimberly D. M.; Prokopchuk, Ernest M. (2011). "Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)2". <i>Journal of Chemical Education</i>. <b>88</b> (8): 1155–1157. <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/2011JChEd..88.1155C">2011JChEd..88.1155C</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%2Fed100843a">10.1021/ed100843a</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=Coordination+Complexes+as+Catalysts%3A+The+Oxidation+of+Anthracene+by+Hydrogen+Peroxide+in+the+Presence+of+VO%28acac%292&rft.volume=88&rft.issue=8&rft.pages=1155-1157&rft.date=2011&rft_id=info%3Adoi%2F10.1021%2Fed100843a&rft_id=info%3Abibcode%2F2011JChEd..88.1155C&rft.aulast=Charleton&rft.aufirst=Kimberly+D.+M.&rft.au=Prokopchuk%2C+Ernest+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFŠkalameraVeljkovićPtičekSambol2017" class="citation journal cs1">Škalamera, Đani; Veljković, Jelena; Ptiček, Lucija; Sambol, Matija; Mlinarić-Majerski, Kata; Basarić, Nikola (2017). "Synthesis of asymmetrically disubstituted anthracenes". <i>Tetrahedron</i>. <b>73</b> (40): 5892–5899. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tet.2017.08.038">10.1016/j.tet.2017.08.038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Synthesis+of+asymmetrically+disubstituted+anthracenes&rft.volume=73&rft.issue=40&rft.pages=5892-5899&rft.date=2017&rft_id=info%3Adoi%2F10.1016%2Fj.tet.2017.08.038&rft.aulast=%C5%A0kalamera&rft.aufirst=%C4%90ani&rft.au=Veljkovi%C4%87%2C+Jelena&rft.au=Pti%C4%8Dek%2C+Lucija&rft.au=Sambol%2C+Matija&rft.au=Mlinari%C4%87-Majerski%2C+Kata&rft.au=Basari%C4%87%2C+Nikola&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHeilbronHeaton1923" class="citation journal cs1">Heilbron, I. M.; Heaton, J. S. (1923). "9,10-Dibromoanthracene". <i>Organic Syntheses</i>. <b>3</b>: 41. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.003.0041">10.15227/orgsyn.003.0041</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=9%2C10-Dibromoanthracene&rft.volume=3&rft.pages=41&rft.date=1923&rft_id=info%3Adoi%2F10.15227%2Forgsyn.003.0041&rft.aulast=Heilbron&rft.aufirst=I.+M.&rft.au=Heaton%2C+J.+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_28-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Collin, Gerd; Höke, Hartmut and Talbiersky, Jörg (2006) "Anthracene" in <i>Ullmann's Encyclopedia of Industrial Chemistry</i>, Wiley-VCH, Weinheim. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><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%2F14356007.a02_343.pub2">10.1002/14356007.a02_343.pub2</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">Zeitler, Alex (2012-06-27) <a rel="nofollow" class="external text" href="https://www.smta.org/chapters/files/UpperMidwest_BTW_Conformal_Coating_June_27th_2012.pdf">Conformal Coating 101: General Overview, Process Development, and Control Methods</a>. BTW, Inc.</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"><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?Name=1-hydroxyanthracene&Units=SI">1-Hydroxyanthracene</a>. NIST datapage</span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?Name=2-hydroxyanthracene&Units=SI">2-Hydroxyanthracene</a>. NIST datapage</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Cited_sources">Cited sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anthracene&action=edit&section=14" title="Edit section: Cited sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaynes,_William_M.2011" class="citation book cs1">Haynes, William M., ed. (2011). <i><a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics">CRC Handbook of Chemistry and Physics</a></i> (92nd ed.). <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4398-5511-9" title="Special:BookSources/978-1-4398-5511-9"><bdi>978-1-4398-5511-9</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.edition=92nd&rft.pub=CRC+Press&rft.date=2011&rft.isbn=978-1-4398-5511-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></li></ul> <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=Anthracene&action=edit&section=15" title="Edit section: 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rel="nofollow" class="external text" href="https://web.archive.org/web/20091114145131/http://monographs.iarc.fr/ENG/Monographs/vol32/volume32.pdf">IARC – Monograph 32</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060518002254/http://www.npi.gov.au/database/substance-info/profiles/74.html">National Pollutant Inventory – Polycyclic Aromatic Hydrocarbon Fact Sheet</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110122105255/http://echa.europa.eu/home_en.asp">European Chemicals Agency – ECHA</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation encyclopaedia cs1"><span class="cs1-ws-icon" title="s:1911 Encyclopædia Britannica/Anthracene"><a class="external text" href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Anthracene">"Anthracene" </a></span>. <i><a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a></i> (11th ed.). 1911.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Anthracene&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.edition=11th&rft.date=1911&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnthracene" class="Z3988"></span></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 dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol 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.navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Hydrocarbons" 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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><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="Hydrocarbons" 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_+_2" 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 class="mw-selflink selflink">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 href="/wiki/Benzene" title="Benzene">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></div><div role="navigation" class="navbox" aria-labelledby="Tricyclics" 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:Tricyclics" title="Template:Tricyclics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tricyclics" title="Template talk:Tricyclics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tricyclics" title="Special:EditPage/Template:Tricyclics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Tricyclics" style="font-size:114%;margin:0 4em"><a href="/wiki/Tricyclic" title="Tricyclic">Tricyclics</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_class" class="mw-redirect" title="Chemical class">Classes</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/Acridine" title="Acridine">Acridine</a></li> <li><a class="mw-selflink selflink">Anthracene</a></li> <li><a href="/wiki/Dibenzazepine" title="Dibenzazepine">Dibenzazepine</a></li> <li><a href="/wiki/Dibenzocycloheptene" title="Dibenzocycloheptene">Dibenzocycloheptene</a></li> <li><a href="/w/index.php?title=Dibenzodiazepine&action=edit&redlink=1" class="new" title="Dibenzodiazepine (page does not exist)">Dibenzodiazepine</a></li> <li><a href="/wiki/Dibenzothiazepine" title="Dibenzothiazepine">Dibenzothiazepine</a></li> <li><a href="/wiki/Dibenzothiepin" title="Dibenzothiepin">Dibenzothiepin</a></li> <li><a href="/wiki/Dibenzoxazepine" class="mw-redirect" title="Dibenzoxazepine">Dibenzoxazepine</a></li> <li><a href="/wiki/Dibenzoxepin" title="Dibenzoxepin">Dibenzoxepin</a></li> <li><a href="/wiki/Phenothiazine" title="Phenothiazine">Phenothiazine</a></li> <li><a href="/wiki/Pyridazinobenzoxazine" class="mw-redirect" title="Pyridazinobenzoxazine">Pyridazinobenzoxazine</a></li> <li><a href="/wiki/Pyridinobenzodiazepine" class="mw-redirect" title="Pyridinobenzodiazepine">Pyridinobenzodiazepine</a></li> <li><a href="/wiki/Thioxanthene" title="Thioxanthene">Thioxanthene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antidepressant" title="Antidepressant">Antidepressants</a><br />(<a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> <span class="nobold">(TCAs)</span>)</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/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Amezepine" title="Amezepine">Amezepine</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/wiki/Amitriptylinoxide" title="Amitriptylinoxide">Amitriptylinoxide</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Aptazapine" title="Aptazapine">Aptazapine</a></li> <li><a href="/wiki/Azepindole" title="Azepindole">Azepindole</a></li> <li><a href="/wiki/Batelapine" title="Batelapine">Batelapine</a></li> <li><a href="/w/index.php?title=Beloxepin&action=edit&redlink=1" class="new" title="Beloxepin (page does not exist)">Beloxepin</a></li> <li><a href="/wiki/Butriptyline" title="Butriptyline">Butriptyline</a></li> <li><a href="/wiki/Cianopramine" title="Cianopramine">Cianopramine</a></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Cidoxepin" title="Cidoxepin">Cidoxepin</a></li> <li><a href="/wiki/Clomipramine" title="Clomipramine">Clomipramine</a></li> <li><a href="/wiki/Cotriptyline" title="Cotriptyline">Cotriptyline</a></li> <li><a href="/wiki/Cyanodothiepin" title="Cyanodothiepin">Cyanodothiepin</a></li> <li><a href="/wiki/Demexiptiline" title="Demexiptiline">Demexiptiline</a></li> <li><a href="/wiki/Depramine" title="Depramine">Depramine (balipramine)</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine (desmethylimipramine)</a></li> <li><a href="/wiki/Desmethylclomipramine" class="mw-redirect" title="Desmethylclomipramine">Desmethylclomipramine</a></li> <li><a href="/w/index.php?title=Desmethyltrimipramine&action=edit&redlink=1" class="new" title="Desmethyltrimipramine (page does not exist)">Desmethyltrimipramine</a></li> <li><a href="/wiki/Dibenzepin" title="Dibenzepin">Dibenzepin</a></li> <li><a href="/wiki/Dimetacrine" title="Dimetacrine">Dimetacrine</a></li> <li><a href="/wiki/Dosulepin" title="Dosulepin">Dosulepin (dothiepin)</a></li> <li><a href="/wiki/Doxepin" title="Doxepin">Doxepin</a></li> <li><a href="/wiki/Enprazepine" title="Enprazepine">Enprazepine</a></li> <li><a href="/w/index.php?title=Fantridone&action=edit&redlink=1" class="new" title="Fantridone (page does not exist)">Fantridone</a></li> <li><a href="/wiki/Fluotracen" title="Fluotracen">Fluotracen</a></li> <li><a href="/wiki/Hepzidine" title="Hepzidine">Hepzidine</a></li> <li><a href="/wiki/Homopipramol" title="Homopipramol">Homopipramol</a></li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/Imipraminoxide" title="Imipraminoxide">Imipraminoxide</a></li> <li><a href="/wiki/Intriptyline" title="Intriptyline">Intriptyline</a></li> <li><a href="/wiki/Iprindole" title="Iprindole">Iprindole</a></li> <li><a href="/wiki/Ketipramine" title="Ketipramine">Ketipramine</a></li> <li><a href="/wiki/Litracen" title="Litracen">Litracen</a></li> <li><a href="/wiki/Lofepramine" title="Lofepramine">Lofepramine</a></li> <li><a href="/wiki/Losindole" title="Losindole">Losindole</a></li> <li><a href="/wiki/Loxapine" title="Loxapine">Loxapine</a></li> <li><a href="/wiki/Maprotiline" title="Maprotiline">Maprotiline</a></li> <li><a href="/wiki/Mariptiline" title="Mariptiline">Mariptiline</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Melitracen" title="Melitracen">Melitracen</a></li> <li><a href="/wiki/Metapramine" title="Metapramine">Metapramine</a></li> <li><a href="/wiki/Mezepine" title="Mezepine">Mezepine</a></li> <li><a href="/wiki/Mirtazapine" title="Mirtazapine">Mirtazapine</a></li> <li><a href="/wiki/Monometacrine" title="Monometacrine">Monometacrine</a></li> <li><a href="/wiki/Nitroxazepine" title="Nitroxazepine">Nitroxazepine</a></li> <li><a href="/w/index.php?title=Norbutriptyline&action=edit&redlink=1" class="new" title="Norbutriptyline (page does not exist)">Norbutriptyline</a></li> <li><a href="/wiki/Nordoxepin" title="Nordoxepin">Nordoxepin</a></li> <li><a href="/wiki/Northiaden" title="Northiaden">Northiaden (nordosulepin)</a></li> <li><a href="/wiki/Nortriptyline" title="Nortriptyline">Nortriptyline (noramitriptyline)</a></li> <li><a href="/wiki/Noxiptiline" title="Noxiptiline">Noxiptiline</a></li> <li><a href="/wiki/Octriptyline" title="Octriptyline">Octriptyline</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/Pipofezine" title="Pipofezine">Pipofezine</a></li> <li><a href="/wiki/Pirandamine" title="Pirandamine">Pirandamine</a></li> <li><a href="/wiki/Propizepine" title="Propizepine">Propizepine</a></li> <li><a href="/wiki/Protriptyline" title="Protriptyline">Protriptyline</a></li> <li><a href="/wiki/Quinupramine" title="Quinupramine">Quinupramine</a></li> <li><a href="/w/index.php?title=Spiroxepin&action=edit&redlink=1" class="new" title="Spiroxepin (page does not exist)">Spiroxepin</a></li> <li><a href="/wiki/Tandamine" title="Tandamine">Tandamine</a></li> <li><a href="/wiki/Tampramine" title="Tampramine">Tampramine</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Tienopramine" title="Tienopramine">Tienopramine</a></li> <li><a href="/wiki/Trimipramine" title="Trimipramine">Trimipramine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histamine_antagonist" class="mw-redirect" title="Histamine antagonist">Antihistamines</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/Azatadine" title="Azatadine">Azatadine</a></li> <li><a href="/wiki/Bisulepin" title="Bisulepin">Bisulepin</a></li> <li><a href="/wiki/Cidoxepin" title="Cidoxepin">Cidoxepin</a></li> <li><a href="/wiki/Clobenzepam" title="Clobenzepam">Clobenzepam</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dacemazine" title="Dacemazine">Dacemazine</a></li> <li><a href="/wiki/Deptropine" title="Deptropine">Deptropine</a></li> <li><a href="/wiki/Desloratadine" title="Desloratadine">Desloratadine</a></li> <li><a href="/wiki/Epinastine" title="Epinastine">Epinastine</a></li> <li><a href="/wiki/Etymemazine" title="Etymemazine">Etymemazine</a></li> <li><a href="/wiki/Fenethazine" title="Fenethazine">Fenethazine</a></li> <li><a href="/wiki/Hydroxyethylpromethazine" title="Hydroxyethylpromethazine">Hydroxyethylpromethazine</a></li> <li><a href="/wiki/Isopromethazine" title="Isopromethazine">Isopromethazine</a></li> <li><a href="/wiki/Isothipendyl" title="Isothipendyl">Isothipendyl</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Mebhydrolin" title="Mebhydrolin">Mebhydrolin</a></li> <li><a href="/wiki/Mequitazine" title="Mequitazine">Mequitazine</a></li> <li><a href="/wiki/Methdilazine" title="Methdilazine">Methdilazine</a></li> <li><a href="/wiki/Olopatadine" title="Olopatadine">Olopatadine</a></li> <li><a href="/wiki/Oxomemazine" title="Oxomemazine">Oxomemazine</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Phenindamine" title="Phenindamine">Phenindamine</a></li> <li><a href="/wiki/Pimethixene" title="Pimethixene">Pimethixene</a></li> <li><a href="/wiki/Pirolate" title="Pirolate">Pirolate</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propiomazine" title="Propiomazine">Propiomazine</a></li> <li><a href="/wiki/Rupatadine" title="Rupatadine">Rupatadine</a></li> <li><a href="/wiki/Thiazinamium" class="mw-redirect" title="Thiazinamium">Thiazinamium</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</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/Acetophenazine" title="Acetophenazine">Acetophenazine</a></li> <li><a href="/wiki/Alimemazine" title="Alimemazine">Alimemazine</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/Butaperazine" title="Butaperazine">Butaperazine</a></li> <li><a href="/wiki/Carfenazine" title="Carfenazine">Carfenazine (carphenazine)</a></li> <li><a href="/wiki/Carpipramine" title="Carpipramine">Carpipramine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chlorprothixene" title="Chlorprothixene">Chlorprothixene</a></li> <li><a href="/wiki/Ciclindole" title="Ciclindole">Ciclindole</a></li> <li><a href="/w/index.php?title=Citatepine&action=edit&redlink=1" class="new" title="Citatepine (page does not exist)">Citatepine</a></li> <li><a href="/wiki/Clocapramine" title="Clocapramine">Clocapramine</a></li> <li><a href="/wiki/Clomacran" title="Clomacran">Clomacran</a></li> <li><a href="/wiki/Clorotepine" title="Clorotepine">Clorotepine</a></li> <li><a href="/wiki/Clotiapine" title="Clotiapine">Clotiapine</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/w/index.php?title=Cyanothepin&action=edit&redlink=1" class="new" title="Cyanothepin (page does not exist)">Cyanothepin</a></li> <li><a href="/w/index.php?title=Doclothepin&action=edit&redlink=1" class="new" title="Doclothepin (page does not exist)">Doclothepin</a></li> <li><a href="/w/index.php?title=Docloxythepin&action=edit&redlink=1" class="new" title="Docloxythepin (page does not exist)">Docloxythepin</a></li> <li><a href="/w/index.php?title=Erizepine&action=edit&redlink=1" class="new" title="Erizepine (page does not exist)">Erizepine</a></li> <li><a href="/wiki/Flucindole" title="Flucindole">Flucindole</a></li> <li><a href="/wiki/Flumezapine" title="Flumezapine">Flumezapine</a></li> <li><a href="/wiki/Fluotracen" title="Fluotracen">Fluotracen</a></li> <li><a href="/wiki/Flupentixol" title="Flupentixol">Flupentixol</a></li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Gevotroline" title="Gevotroline">Gevotroline</a></li> <li><a href="/wiki/Homopipramol" title="Homopipramol">Homopipramol</a></li> <li><a href="/w/index.php?title=Isofloxythepin&action=edit&redlink=1" class="new" title="Isofloxythepin (page does not exist)">Isofloxythepin</a></li> <li><a href="/wiki/Levomepromazine" title="Levomepromazine">Levomepromazine/Methotrimeprazine</a></li> <li><a href="/wiki/Loxapine" title="Loxapine">Loxapine</a></li> <li><a href="/w/index.php?title=Maroxepin&action=edit&redlink=1" class="new" title="Maroxepin (page does not exist)">Maroxepin</a></li> <li><a href="/w/index.php?title=Meperathiepin&action=edit&redlink=1" class="new" title="Meperathiepin (page does not exist)">Meperathiepin</a></li> <li><a href="/wiki/Mesoridazine" title="Mesoridazine">Mesoridazine</a></li> <li><a href="/wiki/Metiapine" title="Metiapine">Metiapine</a></li> <li><a href="/wiki/Metitepine" title="Metitepine">Metitepine</a></li> <li><a href="/w/index.php?title=Metoxepin&action=edit&redlink=1" class="new" title="Metoxepin (page does not exist)">Metoxepin</a></li> <li><a href="/wiki/Mosapramine" title="Mosapramine">Mosapramine</a></li> <li><a href="/wiki/Naranol" title="Naranol">Naranol</a></li> <li><a href="/w/index.php?title=Octomethothepin&action=edit&redlink=1" class="new" title="Octomethothepin (page does not exist)">Octomethothepin</a></li> <li><a href="/wiki/Olanzapine" title="Olanzapine">Olanzapine</a></li> <li><a href="/w/index.php?title=Oxyclothepin&action=edit&redlink=1" class="new" title="Oxyclothepin (page does not exist)">Oxyclothepin</a></li> <li><a href="/wiki/Oxyprothepin" class="mw-redirect" title="Oxyprothepin">Oxyprothepin</a></li> <li><a href="/w/index.php?title=Pentiapine&action=edit&redlink=1" class="new" title="Pentiapine (page does not exist)">Pentiapine</a></li> <li><a href="/w/index.php?title=Peradithiepin&action=edit&redlink=1" class="new" title="Peradithiepin (page does not exist)">Peradithiepin</a></li> <li><a href="/wiki/Perathiepin" title="Perathiepin">Perathiepin</a></li> <li><a href="/wiki/Perazine" title="Perazine">Perazine</a></li> <li><a href="/wiki/Perphenazine" title="Perphenazine">Perphenazine</a></li> <li><a href="/wiki/Periciazine" title="Periciazine">Periciazine</a></li> <li><a href="/wiki/Pinoxepin" title="Pinoxepin">Pinoxepin</a></li> <li><a href="/wiki/Piperacetazine" title="Piperacetazine">Piperacetazine</a></li> <li><a href="/wiki/Pipotiazine" title="Pipotiazine">Pipotiazine</a></li> <li><a href="/wiki/Piquindone" title="Piquindone">Piquindone</a></li> <li><a href="/wiki/Prochlorperazine" title="Prochlorperazine">Prochlorperazine</a></li> <li><a href="/wiki/Promazine" title="Promazine">Promazine</a></li> <li><a href="/wiki/Prothipendyl" title="Prothipendyl">Prothipendyl</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/w/index.php?title=Savoxepin&action=edit&redlink=1" class="new" title="Savoxepin (page does not exist)">Savoxepin/Cipazoxapine</a></li> <li><a href="/wiki/Sulforidazine" title="Sulforidazine">Sulforidazine</a></li> <li><a href="/wiki/Tenilapine" title="Tenilapine">Tenilapine</a></li> <li><a href="/wiki/Thiethylperazine" title="Thiethylperazine">Thiethylperazine</a></li> <li><a href="/wiki/Thiopropazate" title="Thiopropazate">Thiopropazate</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/w/index.php?title=Tilozepine&action=edit&redlink=1" class="new" title="Tilozepine (page does not exist)">Tilozepine</a></li> <li><a href="/w/index.php?title=Traboxopine&action=edit&redlink=1" class="new" title="Traboxopine (page does not exist)">Traboxopine</a></li> <li><a href="/wiki/Trifluoperazine" title="Trifluoperazine">Trifluoperazine</a></li> <li><a href="/wiki/Triflupromazine" title="Triflupromazine">Triflupromazine</a></li> <li><a href="/w/index.php?title=Trifluthepin&action=edit&redlink=1" class="new" title="Trifluthepin (page does not exist)">Trifluthepin</a></li> <li><a href="/wiki/Zotepine" title="Zotepine">Zotepine</a></li> <li><a href="/wiki/Zuclopenthixol" title="Zuclopenthixol">Zuclopenthixol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</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/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine</a></li> <li><a href="/wiki/Eslicarbazepine" class="mw-redirect" title="Eslicarbazepine">Eslicarbazepine</a></li> <li><a href="/wiki/Eslicarbazepine_acetate" title="Eslicarbazepine acetate">Eslicarbazepine acetate</a></li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Licarbazepine" title="Licarbazepine">Licarbazepine</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a></li> <li><a href="/wiki/Oxitriptyline" title="Oxitriptyline">Oxitriptyline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticholinergic" title="Anticholinergic">Anticholinergics</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="/w/index.php?title=Darenzepine&action=edit&redlink=1" class="new" title="Darenzepine (page does not exist)">Darenzepine</a></li> <li><a href="/w/index.php?title=Dipitramine&action=edit&redlink=1" class="new" title="Dipitramine (page does not exist)">Dipitramine</a></li> <li><a href="/w/index.php?title=Nuvenzepine&action=edit&redlink=1" class="new" title="Nuvenzepine (page does not exist)">Nuvenzepine</a></li> <li><a href="/wiki/Pirenzepine" title="Pirenzepine">Pirenzepine</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine</a></li> <li><a href="/w/index.php?title=Rispenzepine&action=edit&redlink=1" class="new" title="Rispenzepine (page does not exist)">Rispenzepine</a></li> <li><a href="/w/index.php?title=Siltenzepine&action=edit&redlink=1" class="new" title="Siltenzepine (page does not exist)">Siltenzepine</a></li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li> <li><a href="/wiki/Tripitramine" title="Tripitramine">Tripitramine</a></li> <li><a href="/wiki/Tropatepine" title="Tropatepine">Tropatepine</a></li> <li><a href="/w/index.php?title=Zolenzepine&action=edit&redlink=1" class="new" title="Zolenzepine (page does not exist)">Zolenzepine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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/Adosopine" title="Adosopine">Adosopine</a></li> <li><a href="/w/index.php?title=Aminopromazine&action=edit&redlink=1" class="new" title="Aminopromazine (page does not exist)">Aminopromazine</a></li> <li><a href="/wiki/Atiprosin" title="Atiprosin">Atiprosin</a></li> <li><a href="/wiki/Benzoctamine" title="Benzoctamine">Benzoctamine</a></li> <li><a href="/wiki/Botiacrine" title="Botiacrine">Botiacrine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/w/index.php?title=Damotepine&action=edit&redlink=1" class="new" title="Damotepine (page does not exist)">Damotepine</a></li> <li><a href="/w/index.php?title=Elanzepine&action=edit&redlink=1" class="new" title="Elanzepine (page does not exist)">Elanzepine</a></li> <li><a href="/w/index.php?title=Fluradoline&action=edit&redlink=1" class="new" title="Fluradoline (page does not exist)">Fluradoline</a></li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylene blue</a></li> <li><a href="/wiki/Monatepil" title="Monatepil">Monatepil</a></li> <li><a href="/wiki/Oxetorone" title="Oxetorone">Oxetorone</a></li> <li><a href="/wiki/Pipazethate" class="mw-redirect" title="Pipazethate">Pipazethate</a></li> <li><a href="/wiki/P7C3" title="P7C3">P7C3</a></li> <li><a href="/w/index.php?title=Pinadoline&action=edit&redlink=1" class="new" title="Pinadoline (page does not exist)">Pinadoline</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Serazapine" title="Serazapine">Serazapine</a></li> <li><a href="/wiki/Tipindole" title="Tipindole">Tipindole</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="Polycyclic_aromatic_hydrocarbons" 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" style="text-align: center;"><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:PAHs" title="Template:PAHs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PAHs" title="Template talk:PAHs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PAHs" title="Special:EditPage/Template:PAHs"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polycyclic_aromatic_hydrocarbons" style="font-size:114%;margin:0 4em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">2 rings</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/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">3 rings</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/Acenaphthene" title="Acenaphthene">Acenaphthene</a></li> <li><a href="/wiki/Acenaphthylene" title="Acenaphthylene">Acenaphthylene</a></li> <li><a class="mw-selflink selflink">Anthracene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Phenalene" title="Phenalene">Phenalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">4 rings</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/Benz(a)anthracene" title="Benz(a)anthracene">Benz[<i>a</i>]anthracene</a></li> <li><a href="/wiki/Benzo(a)fluorene" title="Benzo(a)fluorene">Benzo[<i>a</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">Benzo[<i>c</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)phenanthrene" title="Benzo(c)phenanthrene">Benzo[<i>c</i>]phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Fluoranthene" title="Fluoranthene">Fluoranthene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Triphenylene" title="Triphenylene">Triphenylene</a></li> <li><a href="/wiki/Tricyclobutabenzene" title="Tricyclobutabenzene">Tricyclobutabenzene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">5 rings</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/Benz(e)acephenanthrylene" title="Benz(e)acephenanthrylene">Benz[<i>e</i>]acephenanthrylene</a></li> <li><a href="/wiki/Benzopyrene" title="Benzopyrene">Benzopyrene</a> <ul><li><a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a></li> <li><a href="/wiki/Benzo(e)pyrene" title="Benzo(e)pyrene">Benzo[<i>e</i>]pyrene</a></li> <li><a href="/wiki/Olympicene" title="Olympicene">6<i>H</i>-Benzo[<i>cd</i>]pyrene(Olympicene)</a></li></ul></li> <li><a href="/wiki/Benzo(a)fluoranthene" title="Benzo(a)fluoranthene">Benzo[<i>a</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(b)fluoranthene" class="mw-redirect" title="Benzo(b)fluoranthene">Benzo[<i>b</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(j)fluoranthene" title="Benzo(j)fluoranthene">Benzo[<i>j</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(k)fluoranthene" title="Benzo(k)fluoranthene">Benzo[<i>k</i>]fluoranthene</a></li> <li><a href="/wiki/Bicalicene" title="Bicalicene">trans-Bicalicene</a></li> <li><a href="/wiki/Dibenz(a,h)anthracene" title="Dibenz(a,h)anthracene">Dibenz[<i>a</i>,<i>h</i>]anthracene</a></li> <li><a href="/wiki/Dibenz(a,j)anthracene" title="Dibenz(a,j)anthracene">Dibenz[<i>a</i>,<i>j</i>]anthracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/w/index.php?title=Pentaphene&action=edit&redlink=1" class="new" title="Pentaphene (page does not exist)">Pentaphene</a></li> <li><a href="/wiki/Perylene" title="Perylene">Perylene</a></li> <li><a href="/wiki/Picene" title="Picene">Picene</a></li> <li><a href="/wiki/Tetraphenylene" title="Tetraphenylene">Tetraphenylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">6 rings</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/Anthanthrene" title="Anthanthrene">Anthanthrene</a></li> <li><a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">Benzo[<i>ghi</i>]perylene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">Dibenzopyrenes</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Triangulene" title="Triangulene">Triangulene</a></li> <li><a href="/wiki/Zethrene" title="Zethrene">Zethrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">7+ rings</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/Coronene" title="Coronene">Coronene</a></li> <li><a href="/wiki/Dicoronylene" title="Dicoronylene">Dicoronylene</a></li> <li><a href="/wiki/Diindenoperylene" title="Diindenoperylene">Diindenoperylene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li> <li><a href="/wiki/Hexabenzocoronene" title="Hexabenzocoronene">Hexabenzocoronene</a> (<a href="/wiki/Hexa-cata-hexabenzocoronene" title="Hexa-cata-hexabenzocoronene">Hexa-cata-</a>)</li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li> <li><a href="/wiki/Ovalene" title="Ovalene">Ovalene</a></li> <li><a href="/wiki/Rubicene" title="Rubicene">Rubicene</a></li> <li><a href="/wiki/Rubrene" title="Rubrene">Rubrene</a></li> <li><a href="/wiki/Sumanene" title="Sumanene">Sumanene</a></li> <li><a href="/wiki/Superphenalene" title="Superphenalene">Superphenalene</a></li> <li><a href="/wiki/Trinaphthylene" title="Trinaphthylene">Trinaphthylene</a></li> <li><a href="/wiki/Truxene" title="Truxene">Truxene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">General classes</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/Acene" title="Acene">Acene</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulene</a></li> <li><a href="/wiki/Cyclacene" title="Cyclacene">Cyclacene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicene</a></li> <li><a href="/wiki/Phenacene" title="Phenacene">Phenacene</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="Molecules_detected_in_outer_space" 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_space" 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/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/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></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_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/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" 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="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">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/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/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</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/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/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</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="/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/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="/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/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</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="/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/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</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/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</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/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/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</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/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</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/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</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 href="/wiki/Benzene" title="Benzene">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/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/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</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/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</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></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/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></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 class="mw-selflink selflink">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</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="/wiki/Hemolithin" title="Hemolithin">Hemolithin</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/Carbon" title="Carbon">Linear C<sub>5</sub></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 band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" 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 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