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class="vector-toc-list"> <li id="toc-Acidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Acidity</span> </div> </a> <ul id="toc-Acidity-sublist" class="vector-toc-list"> <li id="toc-Hydrogen_bonding" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydrogen_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.1</span> <span>Hydrogen bonding</span> </div> </a> <ul id="toc-Hydrogen_bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tautomerism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tautomerism"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.2</span> <span>Tautomerism</span> </div> </a> <ul id="toc-Tautomerism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Cumene_process" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cumene_process"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Cumene process</span> </div> </a> <ul id="toc-Cumene_process-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation_of_benzene,_toluene,_cyclohexylbenzene" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation_of_benzene,_toluene,_cyclohexylbenzene"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Oxidation of benzene, toluene, cyclohexylbenzene</span> </div> </a> <ul id="toc-Oxidation_of_benzene,_toluene,_cyclohexylbenzene-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Older_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Older_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Older methods</span> </div> </a> <ul id="toc-Older_methods-sublist" class="vector-toc-list"> <li id="toc-Hydrolysis_of_benzenesulfonic_acid" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydrolysis_of_benzenesulfonic_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.1</span> <span>Hydrolysis of benzenesulfonic acid</span> </div> </a> <ul id="toc-Hydrolysis_of_benzenesulfonic_acid-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrolysis_of_chlorobenzene" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydrolysis_of_chlorobenzene"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.2</span> <span>Hydrolysis of chlorobenzene</span> </div> </a> <ul id="toc-Hydrolysis_of_chlorobenzene-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Coal_pyrolysis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Coal_pyrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.3</span> <span>Coal pyrolysis</span> </div> </a> <ul id="toc-Coal_pyrolysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Miscellaneous_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Miscellaneous_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Miscellaneous methods</span> </div> </a> <ul id="toc-Miscellaneous_methods-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">3</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-Chemicals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Chemicals</span> </div> </a> <ul id="toc-Chemicals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Topical_anesthetic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Topical_anesthetic"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Topical anesthetic</span> </div> </a> <ul id="toc-Topical_anesthetic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nerve_block" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nerve_block"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Nerve block</span> </div> </a> <ul id="toc-Nerve_block-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>History</span> </div> </a> <button aria-controls="toc-History-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 History subsection</span> </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Second_World_War" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Second_World_War"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Second World War</span> </div> </a> <ul id="toc-Second_World_War-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrences" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrences"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Occurrences</span> </div> </a> <ul id="toc-Occurrences-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biodegradation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biodegradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Biodegradation</span> </div> </a> <ul id="toc-Biodegradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety_and_handling" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety_and_handling"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Safety and handling</span> </div> </a> <button aria-controls="toc-Safety_and_handling-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 Safety and handling subsection</span> </button> <ul id="toc-Safety_and_handling-sublist" class="vector-toc-list"> <li id="toc-Shipping" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Shipping"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Shipping</span> </div> </a> <ul id="toc-Shipping-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Phenols" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phenols"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Phenols</span> </div> </a> <ul id="toc-Phenols-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">9</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">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Phenol</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 83 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-83" 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">83 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/Fenol" title="Fenol – Afrikaans" lang="af" hreflang="af" data-title="Fenol" 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/%D9%81%D9%8A%D9%86%D9%88%D9%84" title="فينول – Arabic" lang="ar" hreflang="ar" data-title="فينول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Fenol" title="Fenol – Asturian" lang="ast" hreflang="ast" data-title="Fenol" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Fenol" title="Fenol – Azerbaijani" lang="az" hreflang="az" data-title="Fenol" 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/%D9%81%D9%86%D9%88%D9%84" title="فنول – South Azerbaijani" lang="azb" hreflang="azb" data-title="فنول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A7%87%E0%A6%A8%E0%A6%B2" title="ফেনল – Bangla" lang="bn" hreflang="bn" data-title="ফেনল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Phenol" title="Phenol – Minnan" lang="nan" hreflang="nan" data-title="Phenol" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Bashkir" lang="ba" hreflang="ba" data-title="Фенол" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Belarusian" lang="be" hreflang="be" data-title="Фенол" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Bulgarian" lang="bg" hreflang="bg" data-title="Фенол" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fenol" title="Fenol – Bosnian" lang="bs" hreflang="bs" data-title="Fenol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenol" title="Fenol – Catalan" lang="ca" hreflang="ca" data-title="Fenol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BB_%D0%B9%C3%BF%C3%A7%D0%B5%D0%BA%C4%95" title="Карбол йÿçекĕ – Chuvash" lang="cv" hreflang="cv" data-title="Карбол йÿçекĕ" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenol" title="Fenol – Czech" lang="cs" hreflang="cs" data-title="Fenol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ffenol" title="Ffenol – Welsh" lang="cy" hreflang="cy" data-title="Ffenol" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fenol" title="Fenol – Danish" lang="da" hreflang="da" data-title="Fenol" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenol" title="Phenol – German" lang="de" hreflang="de" data-title="Phenol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Fenool" title="Fenool – Estonian" lang="et" hreflang="et" data-title="Fenool" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%B1%CE%B9%CE%BD%CF%8C%CE%BB%CE%B7" title="Φαινόλη – Greek" lang="el" hreflang="el" data-title="Φαινόλη" 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/Fenol" title="Fenol – Spanish" lang="es" hreflang="es" data-title="Fenol" 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/Fenolo" title="Fenolo – Esperanto" lang="eo" hreflang="eo" data-title="Fenolo" 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/Fenol" title="Fenol – Basque" lang="eu" hreflang="eu" data-title="Fenol" 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/%D9%81%D9%86%D9%88%D9%84" title="فنول – Persian" lang="fa" hreflang="fa" data-title="فنول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Phenol" title="Phenol – Faroese" lang="fo" hreflang="fo" data-title="Phenol" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ph%C3%A9nol_(compos%C3%A9)" title="Phénol (composé) – French" lang="fr" hreflang="fr" data-title="Phénol (composé)" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Fenol" title="Fenol – Western Frisian" lang="fy" hreflang="fy" data-title="Fenol" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Fean%C3%B3l" title="Feanól – Irish" lang="ga" hreflang="ga" data-title="Feanól" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Fenol" title="Fenol – Galician" lang="gl" hreflang="gl" data-title="Fenol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%86%80" title="페놀 – Korean" lang="ko" hreflang="ko" data-title="페놀" 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/%D5%96%D5%A5%D5%B6%D5%B8%D5%AC" title="Ֆենոլ – Armenian" lang="hy" hreflang="hy" data-title="Ֆենոլ" 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%AB%E0%A4%BF%E0%A4%A8%E0%A5%8B%E0%A4%B2" title="फिनोल – Hindi" lang="hi" hreflang="hi" data-title="फिनोल" 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/Fenol" title="Fenol – Croatian" lang="hr" hreflang="hr" data-title="Fenol" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Fenolo" title="Fenolo – Ido" lang="io" hreflang="io" data-title="Fenolo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenol" title="Fenol – Indonesian" lang="id" hreflang="id" data-title="Fenol" 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/Fenolo" title="Fenolo – Italian" lang="it" hreflang="it" data-title="Fenolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%95%D7%9C" title="פנול – Hebrew" lang="he" hreflang="he" data-title="פנול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/F%C3%A9nol" title="Fénol – Javanese" lang="jv" hreflang="jv" data-title="Fénol" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A4%E1%83%94%E1%83%9C%E1%83%9D%E1%83%9A%E1%83%98" title="ფენოლი – Georgian" lang="ka" hreflang="ka" data-title="ფენოლი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-csb mw-list-item"><a href="https://csb.wikipedia.org/wiki/Karb%C3%B3l" title="Karból – Kashubian" lang="csb" hreflang="csb" data-title="Karból" data-language-autonym="Kaszëbsczi" data-language-local-name="Kashubian" class="interlanguage-link-target"><span>Kaszëbsczi</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Kazakh" lang="kk" hreflang="kk" data-title="Фенол" 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%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Kyrgyz" lang="ky" hreflang="ky" data-title="Фенол" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Phenolum" title="Phenolum – Latin" lang="la" hreflang="la" data-title="Phenolum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fenols" title="Fenols – Latvian" lang="lv" hreflang="lv" data-title="Fenols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Fenolis" title="Fenolis – Lithuanian" lang="lt" hreflang="lt" data-title="Fenolis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenol" title="Fenol – Hungarian" lang="hu" hreflang="hu" data-title="Fenol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Macedonian" lang="mk" hreflang="mk" data-title="Фенол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AB%E0%B5%80%E0%B4%A8%E0%B5%8B%E0%B5%BE" title="ഫീനോൾ – Malayalam" lang="ml" hreflang="ml" data-title="ഫീനോൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%AB%E0%A5%87%E0%A4%A8%E0%A5%89%E0%A4%B2" title="फेनॉल – Marathi" lang="mr" hreflang="mr" data-title="फेनॉल" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fenol" title="Fenol – Malay" lang="ms" hreflang="ms" data-title="Fenol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-cdo mw-list-item"><a href="https://cdo.wikipedia.org/wiki/G%C4%83-p%C5%8F%CC%A4-l%C4%ADk-k%C3%A1ik-s%C5%8Fng" title="Gă-pŏ̤-lĭk-káik-sŏng – Mindong" lang="cdo" hreflang="cdo" data-title="Gă-pŏ̤-lĭk-káik-sŏng" data-language-autonym="閩東語 / Mìng-dĕ̤ng-ngṳ̄" data-language-local-name="Mindong" class="interlanguage-link-target"><span>閩東語 / Mìng-dĕ̤ng-ngṳ̄</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%80%E1%80%AC%E1%80%98%E1%80%B1%E1%80%AC%E1%80%BA%E1%80%9C%E1%80%85%E1%80%BA%E1%80%A1%E1%80%80%E1%80%BA%E1%80%86%E1%80%85%E1%80%BA" title="ကာဘော်လစ်အက်ဆစ် – Burmese" lang="my" hreflang="my" data-title="ကာဘော်လစ်အက်ဆစ်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenol" title="Fenol – Dutch" lang="nl" hreflang="nl" data-title="Fenol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8E%E3%83%BC%E3%83%AB" title="フェノール – Japanese" lang="ja" hreflang="ja" data-title="フェノール" 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/Fenol" title="Fenol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fenol" 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/Fenol" title="Fenol – Uzbek" lang="uz" hreflang="uz" data-title="Fenol" 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-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D9%81%DB%8C%D9%86%D9%88%D9%84" title="فینول – Western Punjabi" lang="pnb" hreflang="pnb" data-title="فینول" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenol" title="Fenol – Polish" lang="pl" hreflang="pl" data-title="Fenol" 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/Fenol" title="Fenol – Portuguese" lang="pt" hreflang="pt" data-title="Fenol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-kaa mw-list-item"><a href="https://kaa.wikipedia.org/wiki/Fenol" title="Fenol – Kara-Kalpak" lang="kaa" hreflang="kaa" data-title="Fenol" data-language-autonym="Qaraqalpaqsha" data-language-local-name="Kara-Kalpak" class="interlanguage-link-target"><span>Qaraqalpaqsha</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenol" title="Fenol – Romanian" lang="ro" hreflang="ro" data-title="Fenol" 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%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Russian" lang="ru" hreflang="ru" data-title="Фенол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Phenol" title="Phenol – Scots" lang="sco" hreflang="sco" data-title="Phenol" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Fenolet" title="Fenolet – Albanian" lang="sq" hreflang="sq" data-title="Fenolet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/%C3%80citu_f%C3%A8nicu" title="Àcitu fènicu – Sicilian" lang="scn" hreflang="scn" data-title="Àcitu fènicu" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Phenol" title="Phenol – Simple English" lang="en-simple" hreflang="en-simple" data-title="Phenol" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fenol" title="Fenol – Slovak" lang="sk" hreflang="sk" data-title="Fenol" 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/Fenol" title="Fenol – Slovenian" lang="sl" hreflang="sl" data-title="Fenol" 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/Fenol" title="Fenol – Serbian" lang="sr" hreflang="sr" data-title="Fenol" 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/Fenol" title="Fenol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenol" 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/Fenoli" title="Fenoli – Finnish" lang="fi" hreflang="fi" data-title="Fenoli" 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/Fenol" title="Fenol – Swedish" lang="sv" hreflang="sv" data-title="Fenol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Phenol" title="Phenol – Tagalog" lang="tl" hreflang="tl" data-title="Phenol" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AE%BE%E0%AE%B2%E0%AF%8D" title="பீனால் – Tamil" lang="ta" hreflang="ta" data-title="பீனால்" 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%B8%9F%E0%B8%B5%E0%B8%99%E0%B8%AD%E0%B8%A5" title="ฟีนอล – Thai" lang="th" hreflang="th" data-title="ฟีนอล" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Tajik" lang="tg" hreflang="tg" data-title="Фенол" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenol" title="Fenol – Turkish" lang="tr" hreflang="tr" data-title="Fenol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – Ukrainian" lang="uk" hreflang="uk" data-title="Фенол" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%81%DB%8C%D9%86%D9%88%D9%84" title="فینول – Urdu" lang="ur" hreflang="ur" data-title="فینول" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenol" title="Phenol – Vietnamese" lang="vi" hreflang="vi" data-title="Phenol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Phenol" title="Phenol – Waray" lang="war" hreflang="war" data-title="Phenol" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8B%AF%E9%85%9A" title="苯酚 – Wu" lang="wuu" hreflang="wuu" data-title="苯酚" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%8B%AF%E9%85%9A" title="苯酚 – Cantonese" lang="yue" hreflang="yue" data-title="苯酚" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%AF%E9%85%9A" title="苯酚 – Chinese" lang="zh" hreflang="zh" data-title="苯酚" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q130336#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound (C6H5OH)</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the molecule. For the group of chemicals that contains a phenol group, see <a href="/wiki/Phenols" title="Phenols">Phenols</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">"Carbolic acid" redirects here; not to be confused with <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a> or <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Phenol </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Phenol2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Phenol2.svg/80px-Phenol2.svg.png" decoding="async" width="80" height="146" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Phenol2.svg/120px-Phenol2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Phenol2.svg/160px-Phenol2.svg.png 2x" data-file-width="70" data-file-height="128" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Phenol-2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Phenol-2.svg/84px-Phenol-2.svg.png" decoding="async" width="84" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Phenol-2.svg/126px-Phenol-2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Phenol-2.svg/168px-Phenol-2.svg.png 2x" data-file-width="77" data-file-height="133" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Phenol-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Phenol-3D-balls.png/120px-Phenol-3D-balls.png" decoding="async" width="110" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Phenol-3D-balls.png/250px-Phenol-3D-balls.png 1.5x" data-file-width="942" data-file-height="1100" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Phenol-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Phenol-3D-vdW.png/110px-Phenol-3D-vdW.png" decoding="async" width="110" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Phenol-3D-vdW.png/165px-Phenol-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Phenol-3D-vdW.png/220px-Phenol-3D-vdW.png 2x" data-file-width="971" data-file-height="1100" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenol_2_grams.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Phenol_2_grams.jpg/220px-Phenol_2_grams.jpg" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Phenol_2_grams.jpg/330px-Phenol_2_grams.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Phenol_2_grams.jpg/440px-Phenol_2_grams.jpg 2x" data-file-width="500" data-file-height="500" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Phenol<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Benzenol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><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>Carbolic acid</li><li>Phenolic acid</li><li>Phenylic acid</li><li>Hydroxybenzene</li><li>Phenic acid</li><li>Phenyl alcohol</li><li>Phenyl hydroxide</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=108-95-2">108-95-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc1ccccc1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15882">CHEBI:15882</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL14060">ChEMBL14060</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.971.html">971</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/DB03255">DB03255</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/100.003.303">100.003.303</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q130336#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/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/D00033">D00033</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/996">996</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>SJ3325000</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/339NCG44TV">339NCG44TV</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/UN_number" title="UN number">UN number</a> </td> <td>2821 (solution)<br />2312 (molten)<br />1671 (solid) </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/DTXSID5021124">DTXSID5021124</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q130336#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H<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: ISWSIDIOOBJBQZ-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/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">Oc1ccccc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001941130000000000♠"></span>94.113</span> g/mol   </td></tr> <tr> <td>Appearance </td> <td>Transparent crystalline solid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Sweet and tarry </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.07<span class="nowrap"> </span>g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>40.5 °C (104.9 °F; 313.6 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>181.7 °C (359.1 °F; 454.8 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>8.3<span class="nowrap"> </span>g/100 mL (20<span class="nowrap"> </span>°C) </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>1.48<sup id="cite_ref-chemsrc_2-0" class="reference"><a href="#cite_note-chemsrc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>0.4<span class="nowrap"> </span>mmHg (20<span class="nowrap"> </span>°C)<sup id="cite_ref-PGCH_3-0" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>9.95 (in water),</li><li>18.0 (in DMSO),</li><li>29.1 (in acetonitrile)<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></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td>Phenoxide </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>270.75<span class="nowrap"> </span>nm<sup id="cite_ref-pubchem_5-0" class="reference"><a href="#cite_note-pubchem-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/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>1.224<span class="nowrap"> </span><a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_C05" title="ATC code C05">C05BB05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C05BB05">WHO</a></span>) <a href="/wiki/ATC_code_D08" title="ATC code D08">D08AE03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D08AE03">WHO</a></span>), <a href="/wiki/ATC_code_N01" title="ATC code N01">N01BX03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N01BX03">WHO</a></span>), <a href="/wiki/ATC_code_R02" title="ATC code R02">R02AA19</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=R02AA19">WHO</a></span>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><sup id="cite_ref-sigma_6-0" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H301: Toxic if swallowed">H301</abbr>, <abbr class="abbr" title="H311: Toxic in contact with skin">H311</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H331: Toxic if inhaled">H331</abbr>, <abbr class="abbr" title="H341: Suspected of causing genetic defects">H341</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</abbr><sup id="cite_ref-sigma_6-1" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<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="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr><sup id="cite_ref-sigma_6-2" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_cac26dcfb9c9c85a" /></span><map name="ImageMap_cac26dcfb9c9c85a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><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 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</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 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</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>79 °C (174 °F; 352 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>1.8–8.6%<sup id="cite_ref-PGCH_3-1" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>317<span class="nowrap"> </span>mg/kg (rat, oral)</li><li>270<span class="nowrap"> </span>mg/kg (mouse, oral)<sup id="cite_ref-IDLH_7-0" class="reference"><a href="#cite_note-IDLH-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LDLo" title="Lethal dose">lowest published</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>420<span class="nowrap"> </span>mg/kg (rabbit, oral)</li><li>500<span class="nowrap"> </span>mg/kg (dog, oral)</li><li>80<span class="nowrap"> </span>mg/kg (cat, oral)<sup id="cite_ref-IDLH_7-1" class="reference"><a href="#cite_note-IDLH-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>19<span class="nowrap"> </span>ppm (mammal)</li><li>81<span class="nowrap"> </span>ppm (rat)</li><li>69<span class="nowrap"> </span>ppm (mouse)<sup id="cite_ref-IDLH_7-2" class="reference"><a href="#cite_note-IDLH-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 5<span class="nowrap"> </span>ppm (19<span class="nowrap"> </span>mg/m<sup>3</sup>) [skin]<sup id="cite_ref-PGCH_3-2" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>TWA 5<span class="nowrap"> </span>ppm (19<span class="nowrap"> </span>mg/m<sup>3</sup>)</li><li>C 15.6<span class="nowrap"> </span>ppm (60<span class="nowrap"> </span>mg/m<sup>3</sup>) [15-minute] [skin]<sup id="cite_ref-PGCH_3-3" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>250<span class="nowrap"> </span>ppm<sup id="cite_ref-PGCH_3-4" class="reference"><a href="#cite_note-PGCH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external autonumber" href="https://www.chemblink.com/MSDS/MSDSFiles/108-95-2_Sigma-Aldrich.pdf">[1]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/Thiophenol" title="Thiophenol">Thiophenol</a></li><li><a href="/wiki/Sodium_phenoxide" title="Sodium phenoxide">Sodium phenoxide</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464200484&page2=Phenol">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>Phenol</b> (also known as <b>carbolic acid</b>, <b>phenolic acid</b>, or <b>benzenol</b>) is an <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the molecular <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH</span>.<sup id="cite_ref-pubchem_5-1" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is a white <a href="/wiki/Crystal" title="Crystal">crystalline</a> <a href="/wiki/Solid" title="Solid">solid</a> that is <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a>. The molecule consists of a <a href="/wiki/Phenyl_group" title="Phenyl group">phenyl group</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">−C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub></span>) bonded to a <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy group</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">−OH</span>). Mildly <a href="/wiki/Acidic" class="mw-redirect" title="Acidic">acidic</a>, it requires careful handling because it can cause <a href="/wiki/Chemical_burn" title="Chemical burn">chemical burns</a>.<sup id="cite_ref-pubchem_5-2" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Phenol was first extracted from <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>, but today is produced on a large scale (about 7 million tonnes a year) from <a href="/wiki/Petroleum" title="Petroleum">petroleum</a>-derived feedstocks. It is an important industrial <a href="/wiki/Commodity" title="Commodity">commodity</a> as a <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> to many materials and useful compounds.<sup id="cite_ref-Ullmann_8-0" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is primarily used to synthesize <a href="/wiki/Plastics" class="mw-redirect" title="Plastics">plastics</a> and related materials. Phenol and its chemical <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> are essential for production of <a href="/wiki/Polycarbonate" title="Polycarbonate">polycarbonates</a>, <a href="/wiki/Epoxy" title="Epoxy">epoxies</a>, <a href="/wiki/Explosive" title="Explosive">explosives</a> such as <a href="/wiki/Picric_acid" title="Picric acid">picric acid</a>, <a href="/wiki/Bakelite" title="Bakelite">Bakelite</a>, <a href="/wiki/Nylon" title="Nylon">nylon</a>, <a href="/wiki/Detergent" title="Detergent">detergents</a>, <a href="/wiki/Herbicide" title="Herbicide">herbicides</a> such as <a href="/wiki/Phenoxy_herbicide" title="Phenoxy herbicide">phenoxy herbicides</a>, and numerous <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drugs</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenol is an organic compound appreciably <a href="/wiki/Solubility" title="Solubility">soluble</a> in water, with about 84.2 g dissolving in 1000 ml (0.895 <a href="/wiki/Molar_concentration" title="Molar concentration">M</a>). Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are possible. The sodium salt of phenol, <a href="/wiki/Sodium_phenoxide" title="Sodium phenoxide">sodium phenoxide</a>, is far more water-soluble. It is a combustible solid (NFPA rating = 2). When heated, phenol produces flammable vapors that are explosive at concentrations of 3 to 10% in air. Carbon dioxide or dry chemical extinguishers should be used to fight phenol fires.<sup id="cite_ref-pubchem_5-3" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=2" title="Edit section: Acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenol is a weak acid. In aqueous solution in the pH range ca. 8 - 12 it is in equilibrium with the <b>phenolate</b> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>O<sup class="template-chem2-sup">−</sup></span> (also called <b>phenoxide</b> or <b>carbolate</b>):<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> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH ⇌ C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>O<sup class="template-chem2-sup">−</sup> + H<sup class="template-chem2-sup">+</sup></span></dd></dl> <dl><dd><figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Phenol-phenolate_equilibrium.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Phenol-phenolate_equilibrium.svg/330px-Phenol-phenolate_equilibrium.svg.png" decoding="async" width="330" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Phenol-phenolate_equilibrium.svg/500px-Phenol-phenolate_equilibrium.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Phenol-phenolate_equilibrium.svg/960px-Phenol-phenolate_equilibrium.svg.png 2x" data-file-width="3753" data-file-height="674" /></a><figcaption><a href="/wiki/Resonance_structures" class="mw-redirect" title="Resonance structures">Resonance structures</a> of the phenoxide anion</figcaption></figure><div style="clear:left;" class=""></div></dd></dl> <p>Phenol is more acidic than aliphatic alcohols. Its enhanced acidity is attributed to <a href="/wiki/Resonance_stabilization" class="mw-redirect" title="Resonance stabilization">resonance stabilization</a> of <a href="/wiki/Phenolate" class="mw-redirect" title="Phenolate">phenolate</a> anion. In this way, the negative charge on oxygen is delocalized on to the <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">ortho and para</a> carbon atoms through the pi system.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> An alternative explanation involves the sigma framework, postulating that the dominant effect is the <a href="/wiki/Inductive_effect" title="Inductive effect">induction</a> from the more electronegative <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">sp<sup>2</sup> hybridised carbons</a>; the comparatively more powerful inductive withdrawal of electron density that is provided by the sp<sup>2</sup> system compared to an sp<sup>3</sup> system allows for great stabilization of the oxyanion. In support of the second explanation, the <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> of the <a href="/wiki/Enol" title="Enol">enol</a> of <a href="/wiki/Acetone" title="Acetone">acetone</a> in water is 10.9, making it only slightly less acidic than phenol (p<i>K</i><sub>a</sub> 10.0).<sup id="cite_ref-pubchem_5-4" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute little to its stabilization. However, the situation changes when solvation effects are excluded. </p> <div class="mw-heading mw-heading4"><h4 id="Hydrogen_bonding">Hydrogen bonding</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=3" title="Edit section: Hydrogen bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a> and in alkane solvents, phenol <a href="/wiki/Hydrogen_bonds" class="mw-redirect" title="Hydrogen bonds">hydrogen bonds</a> with a wide range of Lewis bases such as <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, and <a href="/wiki/Diethyl_sulfide" title="Diethyl sulfide">diethyl sulfide</a>. The enthalpies of adduct formation and the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">−OH</span> IR frequency shifts accompanying adduct formation have been compiled.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Phenol is classified as a <a href="/wiki/HSAB_theory" title="HSAB theory">hard acid</a>.<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><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Tautomerism">Tautomerism</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=4" title="Edit section: Tautomerism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Phenol_tautomers.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Phenol_tautomers.svg/170px-Phenol_tautomers.svg.png" decoding="async" width="170" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Phenol_tautomers.svg/255px-Phenol_tautomers.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Phenol_tautomers.svg/340px-Phenol_tautomers.svg.png 2x" data-file-width="540" data-file-height="260" /></a><figcaption>Phenol-cyclohexadienone tautomerism</figcaption></figure> <p>Phenol exhibits <a href="/wiki/Keto-enol_tautomerism" class="mw-redirect" title="Keto-enol tautomerism">keto-enol tautomerism</a> with its unstable keto tautomer cyclohexadienone, but the effect is nearly negligible. The equilibrium constant for enolisation is approximately 10<sup>−13</sup>, which means only one in every ten trillion molecules is in the keto form at any moment.<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> The small amount of stabilisation gained by exchanging a C=C bond for a C=O bond is more than offset by the large destabilisation resulting from the loss of aromaticity. Phenol therefore exists essentially entirely in the enol form.<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> 4,4' Substituted cyclohexadienone can undergo a <a href="/wiki/Dienone%E2%80%93phenol_rearrangement" title="Dienone–phenol rearrangement">dienone–phenol rearrangement</a> in acid conditions and form stable 3,4‐disubstituted phenol.<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> </p><p>For substituted phenols, several factors can favor the keto tautomer: (a) additional hydroxy groups (see <a href="/wiki/Resorcinol" title="Resorcinol">resorcinol</a>) (b) annulation as in the formation of <a href="/wiki/Naphthol" title="Naphthol">naphthols</a>, and (c) deprotonation to give the phenolate.<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><p>Phenoxides are <a href="/wiki/Enolate" title="Enolate">enolates</a> stabilised by <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>. Under normal circumstances, phenoxide is more reactive at the oxygen position, but the oxygen position is a "hard" nucleophile whereas the alpha-carbon positions tend to be "soft".<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> </p> <div class="mw-heading mw-heading3"><h3 id="Reactions">Reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=5" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Hockpart2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Hockpart2.svg/220px-Hockpart2.svg.png" decoding="async" width="220" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Hockpart2.svg/330px-Hockpart2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Hockpart2.svg/440px-Hockpart2.svg.png 2x" data-file-width="277" data-file-height="111" /></a><figcaption>The Hock process leading to phenol via <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a> of cumene.</figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phenol-elpot-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Phenol-elpot-3D-vdW.png/250px-Phenol-elpot-3D-vdW.png" decoding="async" width="220" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Phenol-elpot-3D-vdW.png/330px-Phenol-elpot-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Phenol-elpot-3D-vdW.png/500px-Phenol-elpot-3D-vdW.png 2x" data-file-width="663" data-file-height="752" /></a><figcaption>Neutral phenol substructure "shape". An image of a computed electrostatic surface of neutral phenol molecule, showing neutral regions in green, electronegative areas in orange-red, and the electropositive phenolic proton in blue.</figcaption></figure> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Phenol_in_water.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Phenol_in_water.PNG/250px-Phenol_in_water.PNG" decoding="async" width="220" height="209" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Phenol_in_water.PNG/330px-Phenol_in_water.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Phenol_in_water.PNG/500px-Phenol_in_water.PNG 2x" data-file-width="693" data-file-height="657" /></a><figcaption>Phenol water phase diagram: Certain combinations of phenol and water can make two solutions in one bottle.</figcaption></figure> <p>Phenol is highly reactive toward <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a>. The enhanced nucleophilicity is attributed to donation <a href="/wiki/Pi_electron" class="mw-redirect" title="Pi electron">pi electron</a> density from O into the ring. Many groups can be attached to the ring, via <a href="/wiki/Halogenation" title="Halogenation">halogenation</a>, <a href="/wiki/Acylation" title="Acylation">acylation</a>, <a href="/wiki/Sulfonation" class="mw-redirect" title="Sulfonation">sulfonation</a>, and related processes. </p><p>Phenol is so strongly activated that bromination and chlorination lead readily to polysubstitution.<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> The reaction affords 2- and 4-substituted derivatives. The regiochemistry of halogenation changes in strongly acidic solutions where <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">PhOH<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">+</sup></span> predominates. Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, additional nitro groups are introduced, e.g. to give <a href="/wiki/Picric_acid" title="Picric acid">2,4,6-trinitrophenol</a>. <a href="/wiki/Friedel_Crafts_alkylation" class="mw-redirect" title="Friedel Crafts alkylation">Friedel Crafts alkylations</a> of phenol and its derivatives often proceed without catalysts. Alkylating agents include alkyl halides, alkenes, and ketones. Thus, <a href="/wiki/1-Bromoadamantane" title="1-Bromoadamantane">adamantyl-1-bromide</a>, <a href="/wiki/Dicyclopentadiene" title="Dicyclopentadiene">dicyclopentadiene</a>), and <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanones</a> give respectively 4-adamantylphenol, a bis(2-hydroxyphenyl) derivative, and a 4-cyclohexylphenols. <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> and <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxides</a> alkylate phenols in the presence of <a href="/wiki/Solid_acid" title="Solid acid">solid acid</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a> (e.g. certain <a href="/wiki/Zeolite" title="Zeolite">zeolite</a>). <a href="/wiki/Cresol" title="Cresol">Cresols</a> and cumyl phenols can be produced in that way.<sup id="cite_ref-reddy_21-0" class="reference"><a href="#cite_note-reddy-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red. Phenol is neutralized by <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> forming sodium phenate or phenolate, but being weaker than <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a>, it cannot be neutralized by <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a> or <a href="/wiki/Sodium_carbonate" title="Sodium carbonate">sodium carbonate</a> to liberate <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + NaOH → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>ONa + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>When a mixture of phenol and <a href="/wiki/Benzoyl_chloride" title="Benzoyl chloride">benzoyl chloride</a> are shaken in presence of dilute <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> solution, <a href="/w/index.php?title=Phenyl_benzoate&action=edit&redlink=1" class="new" title="Phenyl benzoate (page does not exist)">phenyl benzoate</a> is formed. This is an example of the <a href="/wiki/Schotten%E2%80%93Baumann_reaction" title="Schotten–Baumann reaction">Schotten–Baumann reaction</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>COCl + HOC<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub> → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CO<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub> + HCl</span></dd></dl> <p>Phenol is reduced to <a href="/wiki/Benzene" title="Benzene">benzene</a> when it is distilled with <a href="/wiki/Zinc" title="Zinc">zinc</a> dust or when its vapour is passed over granules of zinc at 400 °C:<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> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + Zn → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub> + ZnO</span></dd></dl> <p>When phenol is treated with <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> in the presence of <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">BF<sub class="template-chem2-sub">3</sub></span>), <a href="/wiki/Anisole" title="Anisole">anisole</a> is obtained as the main product and nitrogen gas as a byproduct. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + CH<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub> → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OCH<sub class="template-chem2-sub">3</sub> + N<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>Phenol and its derivatives react with iron(III) chloride to give intensely colored solutions containing phenoxide complexes. </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=6" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of phenol's commercial importance, many methods have been developed for its production, but the cumene process is the dominant technology. </p> <div class="mw-heading mw-heading3"><h3 id="Cumene_process">Cumene process</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=7" title="Edit section: Cumene process"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Accounting for 95% of production (2003) is the <a href="/wiki/Cumene_process" title="Cumene process">cumene process</a>, also called <b>Hock process</b>. It involves the partial <a href="/wiki/Redox" title="Redox">oxidation</a> of <a href="/wiki/Cumene" title="Cumene">cumene</a> (isopropylbenzene) via the <a href="/wiki/Hock_rearrangement" class="mw-redirect" title="Hock rearrangement">Hock rearrangement</a>:<sup id="cite_ref-Ullmann_8-1" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Compared to most other processes, the cumene process uses mild conditions and inexpensive raw materials. For the process to be economical, both phenol and the acetone by-product must be in demand.<sup id="cite_ref-essential_chemical_23-0" class="reference"><a href="#cite_note-essential_chemical-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-chemistry.org_24-0" class="reference"><a href="#cite_note-chemistry.org-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In 2010, worldwide demand for acetone was approximately 6.7 million tonnes, 83 percent of which was satisfied with acetone produced by the cumene process. </p><p>A route analogous to the cumene process begins with <a href="/wiki/Cyclohexylbenzene" title="Cyclohexylbenzene">cyclohexylbenzene</a>. It is <a href="/wiki/Oxidized" class="mw-redirect" title="Oxidized">oxidized</a> to a <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxide</a>, akin to the production of <a href="/wiki/Cumene_hydroperoxide" title="Cumene hydroperoxide">cumene hydroperoxide</a>. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>. Cyclohexanone is an important precursor to some <a href="/wiki/Nylon" title="Nylon">nylons</a>.<sup id="cite_ref-acs_phenol_25-0" class="reference"><a href="#cite_note-acs_phenol-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Oxidation_of_benzene,_toluene,_cyclohexylbenzene"><span id="Oxidation_of_benzene.2C_toluene.2C_cyclohexylbenzene"></span>Oxidation of benzene, toluene, cyclohexylbenzene</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=8" title="Edit section: Oxidation of benzene, toluene, cyclohexylbenzene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The direct oxidation of <a href="/wiki/Benzene" title="Benzene">benzene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub></span>) to phenol is possible, but it has not been commercialized: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub> + O → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH</span></dd></dl> <p><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> is a potentially "green" oxidant that is a more potent oxidant than O<sub>2</sub>. Routes for the generation of nitrous oxide however remain uncompetitive.<sup id="cite_ref-CatalysisToday2005_26-0" class="reference"><a href="#cite_note-CatalysisToday2005-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-essential_chemical_23-1" class="reference"><a href="#cite_note-essential_chemical-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-acs_phenol_25-1" class="reference"><a href="#cite_note-acs_phenol-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>An <a href="/wiki/Electrosynthesis" title="Electrosynthesis">electrosynthesis</a> employing <a href="/wiki/Alternating_current" title="Alternating current">alternating current</a> gives phenol from benzene.<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><p>The oxidation of <a href="/wiki/Toluene" title="Toluene">toluene</a>, as developed by <a href="/wiki/Dow_Chemical" class="mw-redirect" title="Dow Chemical">Dow Chemical</a>, involves copper-catalyzed reaction of molten sodium benzoate with air: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">3</sub> + 2 O<sub class="template-chem2-sub">2</sub> → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + CO<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>The reaction is proposed to proceed via formation of benzyoylsalicylate.<sup id="cite_ref-Ullmann_8-2" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Autoxidation" title="Autoxidation">Autoxidation</a> of <a href="/wiki/Cyclohexylbenzene" title="Cyclohexylbenzene">cyclohexylbenzene</a> gives the <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxide</a>. Decomposition of this hydroperoxide affords <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a> and phenol.<sup id="cite_ref-Ullmann_8-3" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Older_methods">Older methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=9" title="Edit section: Older methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Early methods relied on extraction of phenol from coal derivatives or the hydrolysis of benzene derivatives. </p> <div class="mw-heading mw-heading4"><h4 id="Hydrolysis_of_benzenesulfonic_acid">Hydrolysis of benzenesulfonic acid</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=10" title="Edit section: Hydrolysis of benzenesulfonic acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The original commercial route was developed by <a href="/wiki/Bayer" title="Bayer">Bayer</a> and <a href="/wiki/Monsanto" title="Monsanto">Monsanto</a> in the early 1900s, based on discoveries by <a href="/wiki/Charles_Adolphe_Wurtz" title="Charles Adolphe Wurtz">Wurtz</a> and <a href="/wiki/August_Kekul%C3%A9" title="August Kekulé">Kekulé</a>. The method involves the reaction of a strong base with <a href="/wiki/Benzenesulfonate" class="mw-redirect" title="Benzenesulfonate">benzenesulfonic acid</a>, proceeded by the reaction of hydroxide with <a href="/wiki/Sodium_benzenesulfonate" title="Sodium benzenesulfonate">sodium benzenesulfonate</a> to give sodium phenoxide. Acidification of the latter gives phenol. The net conversion is:<sup id="cite_ref-Wittcoff_28-0" class="reference"><a href="#cite_note-Wittcoff-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>SO<sub class="template-chem2-sub">3</sub>H + 2 NaOH → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + Na<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">3</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <div class="mw-heading mw-heading4"><h4 id="Hydrolysis_of_chlorobenzene">Hydrolysis of chlorobenzene</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=11" title="Edit section: Hydrolysis of chlorobenzene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Chlorobenzene" title="Chlorobenzene">Chlorobenzene</a> can be hydrolyzed to phenol using a base (<a href="/wiki/Dow_process_(phenol)" title="Dow process (phenol)">Dow process</a>) or steam (<a href="/wiki/Raschig%E2%80%93Hooker_process" title="Raschig–Hooker process">Raschig–Hooker process</a>):<sup id="cite_ref-chemistry.org_24-1" class="reference"><a href="#cite_note-chemistry.org-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-acs_phenol_25-2" class="reference"><a href="#cite_note-acs_phenol-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Franck_29-0" class="reference"><a href="#cite_note-Franck-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>Cl + NaOH → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + NaCl</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>Cl + H<sub class="template-chem2-sub">2</sub>O → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + HCl</span></dd></dl> <p>These methods suffer from the cost of the chlorobenzene and the need to dispose of the chloride byproduct. </p> <div class="mw-heading mw-heading4"><h4 id="Coal_pyrolysis">Coal pyrolysis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=12" title="Edit section: Coal pyrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenol is also a recoverable byproduct of <a href="/wiki/Coal" title="Coal">coal</a> pyrolysis.<sup id="cite_ref-Franck_29-1" class="reference"><a href="#cite_note-Franck-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> In the <a href="/w/index.php?title=Lummus_process&action=edit&redlink=1" class="new" title="Lummus process (page does not exist)">Lummus process</a>, the oxidation of toluene to <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> is conducted separately. </p> <div class="mw-heading mw-heading3"><h3 id="Miscellaneous_methods">Miscellaneous methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=13" title="Edit section: Miscellaneous methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Amine_to_Phenol_.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Amine_to_Phenol_.jpg/220px-Amine_to_Phenol_.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Amine_to_Phenol_.jpg/330px-Amine_to_Phenol_.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Amine_to_Phenol_.jpg/440px-Amine_to_Phenol_.jpg 2x" data-file-width="3201" data-file-height="2394" /></a><figcaption>Amine to phenol<sup id="cite_ref-:0_30-0" class="reference"><a href="#cite_note-:0-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p><a href="/wiki/Phenyldiazonium" class="mw-redirect" title="Phenyldiazonium">Phenyldiazonium</a> salts hydrolyze to phenol. The method is of no commercial interest since the precursor is expensive.<sup id="cite_ref-:0_30-1" class="reference"><a href="#cite_note-:0-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>NH<sub class="template-chem2-sub">2</sub> + HCl + NaNO<sub class="template-chem2-sub">2</sub> → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + N<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O + NaCl</span></dd></dl> <p><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a> decarboxylates to phenol.<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> </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=Phenol&action=edit&section=14" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Chemicals">Chemicals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=15" title="Edit section: Chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics. <a href="/wiki/Condensation_reaction" title="Condensation reaction">Condensation</a> with acetone gives <a href="/wiki/Bisphenol-A" class="mw-redirect" title="Bisphenol-A">bisphenol-A</a>, a key precursor to <a href="/wiki/Polycarbonate" title="Polycarbonate">polycarbonates</a> and <a href="/wiki/Epoxy" title="Epoxy">epoxide</a> resins. Condensation of phenol, alkylphenols<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. (March 2024)">citation needed</span></a></i>]</sup>, or diphenols <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. (March 2024)">citation needed</span></a></i>]</sup> with <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> gives <a href="/wiki/Phenolic_resin" class="mw-redirect" title="Phenolic resin">phenolic resins</a>, an example of which is <a href="/wiki/Bakelite" title="Bakelite">Bakelite</a>. Partial <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of phenol gives <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>,<sup id="cite_ref-Ullmann_Cyclohexanes_32-0" class="reference"><a href="#cite_note-Ullmann_Cyclohexanes-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> a precursor to <a href="/wiki/Nylon" title="Nylon">nylon</a>. Nonionic <a href="/wiki/Detergent" title="Detergent">detergents</a> are produced by alkylation of phenol to give the <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, e.g., <a href="/wiki/Nonylphenol" title="Nonylphenol">nonylphenol</a>, which are then subjected to <a href="/wiki/Ethoxylation" title="Ethoxylation">ethoxylation</a>.<sup id="cite_ref-Ullmann_8-4" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Phenol is also a versatile precursor to a large collection of drugs, most notably <a href="/wiki/Aspirin" title="Aspirin">aspirin</a> but also many <a href="/wiki/Herbicide" title="Herbicide">herbicides</a> and <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drugs</a>. Phenol is a component in <a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">liquid–liquid</a> <a href="/wiki/Phenol%E2%80%93chloroform_extraction" title="Phenol–chloroform extraction">phenol–chloroform extraction</a> technique used in <a href="/wiki/Molecular_biology" title="Molecular biology">molecular biology</a> for obtaining <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acids</a> from tissues or cell culture samples. Depending on the pH of the solution either <a href="/wiki/DNA" title="DNA">DNA</a> or <a href="/wiki/RNA" title="RNA">RNA</a> can be extracted. </p><p>Phenol is so inexpensive that it also attracts many small-scale uses. It is a component of industrial <a href="/wiki/Paint_stripper" title="Paint stripper">paint strippers</a> used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Safety concerns have caused it to be banned from use in cosmetic products in the <a href="/wiki/European_Union" title="European Union">European Union</a><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Canada" title="Canada">Canada</a>.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Topical_anesthetic">Topical anesthetic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=16" title="Edit section: Topical anesthetic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Concentrated liquid phenol can be used <a href="/wiki/Topical_medication" title="Topical medication">topically</a> as a local <a href="/wiki/Anesthetic" title="Anesthetic">anesthetic</a> for <a href="/wiki/Otology" title="Otology">otology</a> procedures, such as <a href="/wiki/Myringotomy" title="Myringotomy">myringotomy</a> and <a href="/wiki/Tympanotomy" class="mw-redirect" title="Tympanotomy">tympanotomy</a> tube placement, as an alternative to general anesthesia or other local anesthetics.<sup id="cite_ref-drugs_38-0" class="reference"><a href="#cite_note-drugs-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Phenol spray, with phenol as the active ingredient, is used medically to treat sore throat.<sup id="cite_ref-drugs_38-1" class="reference"><a href="#cite_note-drugs-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> It is the active ingredient in some oral <a href="/wiki/Analgesia" class="mw-redirect" title="Analgesia">analgesics</a>.<sup id="cite_ref-drugs_38-2" class="reference"><a href="#cite_note-drugs-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>Concentrated phenol liquids are used for permanent treatment of ingrown toe and finger nails, a procedure known as a chemical <a href="/wiki/Matrixectomy" class="mw-redirect" title="Matrixectomy">matrixectomy</a>. The procedure was first described by Otto Boll in 1945.<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. (February 2025)">citation needed</span></a></i>]</sup> Since then, phenol has become the agent of choice for chemical matrixectomies performed by <a href="/wiki/Podiatrist" title="Podiatrist">podiatrists</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (February 2025)">medical citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Nerve_block">Nerve block</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=17" title="Edit section: Nerve block"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Nerve_block" title="Nerve block">Nerve block</a></div> <p>Phenol is used as a chemical <a href="/wiki/Denervation" title="Denervation">denervation</a> agent in <a href="/wiki/Analgesia" class="mw-redirect" title="Analgesia">analgesia</a> treatment, such as for <a href="/wiki/Spasticity" title="Spasticity">spasticity</a>, arthritis, or cancer pain.<sup id="cite_ref-stat_39-0" class="reference"><a href="#cite_note-stat-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Its effect on the nerve is to <a href="/wiki/Denaturation_(biochemistry)" title="Denaturation (biochemistry)">denature</a> protein, diminish nerve fat and <a href="/wiki/Myelin" title="Myelin">myelin</a> content, and interrupt sensory transmission to the brain.<sup id="cite_ref-stat_39-1" class="reference"><a href="#cite_note-stat-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> If successful, pain relief may last for weeks to two years.<sup id="cite_ref-stat_39-2" class="reference"><a href="#cite_note-stat-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Complications may include pain on injection, bleeding, or infection.<sup id="cite_ref-stat_39-3" class="reference"><a href="#cite_note-stat-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p>Clinical studies from 2023-25 reported that local injection of phenol (1.5–3 ml of 6% phenol in sterile water) at three to five <a href="/wiki/Knee#Nerves" title="Knee">sensory knee nerves</a> was effective as a <a href="/wiki/Neurolysis" title="Neurolysis">neurolytic</a> treatment to relieve pain associated with chronic <a href="/wiki/Osteoarthritis" title="Osteoarthritis">osteoarthritis</a>.<sup id="cite_ref-tay_40-0" class="reference"><a href="#cite_note-tay-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-wilk_41-0" class="reference"><a href="#cite_note-wilk-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> The phenol method may be used for people who did not experience pain relief from <a href="/wiki/Radiofrequency_ablation#Knees" title="Radiofrequency ablation">radiofrequency ablation</a> of knee nerves.<sup id="cite_ref-tay_40-1" class="reference"><a href="#cite_note-tay-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-wilk_41-1" class="reference"><a href="#cite_note-wilk-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=18" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Bottle_of_Phenol.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/Bottle_of_Phenol.jpg/220px-Bottle_of_Phenol.jpg" decoding="async" width="220" height="516" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/5/51/Bottle_of_Phenol.jpg 1.5x" data-file-width="256" data-file-height="600" /></a><figcaption>Bottle of Calvert's phenol antiseptic, <a href="/wiki/Thackray_Museum_of_Medicine" title="Thackray Museum of Medicine">Thackray Museum of Medicine</a><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Phenol was discovered in 1834 by <a href="/wiki/Friedlieb_Ferdinand_Runge" title="Friedlieb Ferdinand Runge">Friedlieb Ferdinand Runge</a>, who extracted it (in impure form) from <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Runge called phenol "Karbolsäure" (coal-oil-acid, carbolic acid). Coal tar remained the primary source until the development of the <a href="/wiki/Petrochemical_industry" title="Petrochemical industry">petrochemical industry</a>. French chemist <a href="/wiki/Auguste_Laurent" title="Auguste Laurent">Auguste Laurent</a> extracted phenol in its pure form, as a derivative of benzene, in 1841.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> In 1836, Auguste Laurent coined the name "phène" for benzene;<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> this is the root of the word "phenol" and "<a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a>". In 1843, French chemist <a href="/wiki/Charles_Fr%C3%A9d%C3%A9ric_Gerhardt" title="Charles Frédéric Gerhardt">Charles Gerhardt</a> coined the name "phénol".<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a> properties of phenol were used by Sir <a href="/wiki/Joseph_Lister" title="Joseph Lister">Joseph Lister</a> in his pioneering technique of antiseptic surgery. Lister decided that the wounds had to be thoroughly cleaned. He then covered the wounds with a piece of rag or lint<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> covered in phenol. The skin irritation caused by continual exposure to phenol eventually led to the introduction of aseptic (germ-free) techniques in surgery. Lister's work was inspired by the works and experiments of his contemporary <a href="/wiki/Louis_Pasteur" title="Louis Pasteur">Louis Pasteur</a> in sterilizing various biological media. He theorized that if germs could be killed or prevented, no infection would occur. Lister reasoned that a chemical could be used to destroy the micro-organisms that cause infection.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>Meanwhile, in <a href="/wiki/Carlisle" title="Carlisle">Carlisle</a>, England, officials were experimenting with <a href="/wiki/Sewage_treatment" title="Sewage treatment">sewage treatment</a> using carbolic acid to reduce the smell of sewage <a href="/wiki/Cesspit" title="Cesspit">cesspools</a>. Having heard of these developments, and having previously experimented with other chemicals for antiseptic purposes without much success, Lister decided to try carbolic acid as a wound antiseptic. He had his first chance on August 12, 1865, when he received a patient: an eleven-year-old boy with a tibia bone fracture which pierced the skin of his lower leg. Ordinarily, amputation would be the only solution. However, Lister decided to try carbolic acid. After setting the bone and supporting the leg with splints, he soaked clean cotton towels in undiluted carbolic acid and applied them to the wound, covered with a layer of tin foil, leaving them for four days. When he checked the wound, Lister was pleasantly surprised to find no signs of infection, just redness near the edges of the wound from mild burning by the carbolic acid. Reapplying fresh bandages with diluted carbolic acid, the boy was able to walk home after about six weeks of treatment.<sup id="cite_ref-BBC_Books_-_Randomhouse_49-0" class="reference"><a href="#cite_note-BBC_Books_-_Randomhouse-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <blockquote><p>By 16 March 1867, when the first results of Lister's work were published in the Lancet, he had treated a total of eleven patients using his new antiseptic method. Of those, only one had died, and that was through a complication that was nothing to do with Lister's wound-dressing technique. Now, for the first time, patients with compound fractures were likely to leave the hospital with all their limbs intact </p><dl><dd>— Richard Hollingham, <i>Blood and Guts: A History of Surgery</i>, p. 62<sup id="cite_ref-BBC_Books_-_Randomhouse_49-1" class="reference"><a href="#cite_note-BBC_Books_-_Randomhouse-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup></dd></dl></blockquote> <blockquote><p>Before antiseptic operations were introduced at the hospital, there were sixteen deaths in thirty-five surgical cases. Almost one in every two patients died. After antiseptic surgery was introduced in the summer of 1865, there were only six deaths in forty cases. The mortality rate had dropped from almost 50 per cent to around 15 per cent. It was a remarkable achievement </p><dl><dd>— Richard Hollingham, <i>Blood and Guts: A History of Surgery</i>, p. 63<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup></dd></dl></blockquote> <p>Phenol was the main ingredient of the "carbolic smoke ball," an ineffective device marketed in London in the 19th century as protection against influenza and other ailments, and the subject of the famous law case <i><a href="/wiki/Carlill_v_Carbolic_Smoke_Ball_Company" class="mw-redirect" title="Carlill v Carbolic Smoke Ball Company">Carlill v Carbolic Smoke Ball Company</a></i>. In the tort law case of <i><a href="/wiki/Roe_v_Minister_of_Health" title="Roe v Minister of Health">Roe v Minister of Health</a></i>, phenol was used to sterilize <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a> packed in <a href="/wiki/Ampoule" title="Ampoule">ampoules</a>, in which it contaminated the anaesthetic through invisible micro-cracks and caused <a href="/wiki/Paraplegia" title="Paraplegia">paraplegia</a> to the plaintiffs. </p> <div class="mw-heading mw-heading3"><h3 id="Second_World_War">Second World War</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=19" title="Edit section: Second World War"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a class="mw-selflink-fragment" href="#Toxicity">toxic effect of phenol</a> on the central nervous system causes sudden collapse and loss of consciousness in both humans and animals; a state of cramping precedes these symptoms because of the motor activity controlled by the central nervous system.<sup id="cite_ref-U_51-0" class="reference"><a href="#cite_note-U-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Injections of phenol were used as a means of individual execution by <a href="/wiki/Nazi_Germany" title="Nazi Germany">Nazi Germany</a> during the <a href="/wiki/Second_World_War" class="mw-redirect" title="Second World War">Second World War</a>.<sup id="cite_ref-TysonNOVA_52-0" class="reference"><a href="#cite_note-TysonNOVA-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> It was originally used by the Nazis in 1939 as part of the mass-murder of disabled people under <i><a href="/wiki/Aktion_T4" title="Aktion T4">Aktion T4</a></i>.<sup id="cite_ref-NaziDrs_53-0" class="reference"><a href="#cite_note-NaziDrs-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> The Germans learned that extermination of smaller groups was more economical by injection of each victim with phenol. Phenol injections were given to thousands of people. <a href="/wiki/Maximilian_Kolbe" title="Maximilian Kolbe">Maximilian Kolbe</a> was also murdered with a phenol injection after surviving two weeks of dehydration and starvation in <a href="/wiki/Auschwitz" class="mw-redirect" title="Auschwitz">Auschwitz</a> when he volunteered to die in place of <a href="/wiki/Franciszek_Gajowniczek" title="Franciszek Gajowniczek">a stranger</a>. Approximately one gram is sufficient to cause death.<sup id="cite_ref-carbolic_54-0" class="reference"><a href="#cite_note-carbolic-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrences">Occurrences</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=20" title="Edit section: Occurrences"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenol is a normal metabolic product, excreted in quantities up to 40 mg/L in human urine.<sup id="cite_ref-U_51-1" class="reference"><a href="#cite_note-U-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Temporal_gland" class="mw-redirect" title="Temporal gland">temporal gland</a> secretion of male <a href="/wiki/Elephant" title="Elephant">elephants</a> showed the presence of phenol and <a href="/wiki/4-methylphenol" class="mw-redirect" title="4-methylphenol">4-methylphenol</a> during <a href="/wiki/Musth" title="Musth">musth</a>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> It is also one of the chemical compounds found in <a href="/wiki/Castoreum" title="Castoreum">castoreum</a>. This compound is ingested from the plants the beaver eats.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>Phenol is a measurable component in the aroma and taste of the distinctive <a href="/wiki/Islay_whisky" class="mw-redirect" title="Islay whisky">Islay scotch whisky</a>,<sup id="cite_ref-auto_58-0" class="reference"><a href="#cite_note-auto-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> generally ~30 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">ppm</a>, but it can be over 160 ppm in the malted <a href="/wiki/Barley" title="Barley">barley</a> used to produce <a href="/wiki/Whisky" title="Whisky">whisky</a>.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> This amount is different from and presumably higher than the amount in the distillate.<sup id="cite_ref-auto_58-1" class="reference"><a href="#cite_note-auto-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biodegradation">Biodegradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=21" title="Edit section: Biodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i><a href="/wiki/Cryptanaerobacter_phenolicus" title="Cryptanaerobacter phenolicus">Cryptanaerobacter phenolicus</a></i> is a bacterium species that produces <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoate</a> from phenol via <a href="/wiki/4-hydroxybenzoate" class="mw-redirect" title="4-hydroxybenzoate">4-hydroxybenzoate</a>.<sup id="cite_ref-Juteau_60-0" class="reference"><a href="#cite_note-Juteau-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> <i><a href="/wiki/Rhodococcus_phenolicus" title="Rhodococcus phenolicus">Rhodococcus phenolicus</a></i> is a bacterium species able to degrade phenol as sole carbon source.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety_and_handling">Safety and handling</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=22" title="Edit section: Safety and handling"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract.<sup id="cite_ref-merck_62-0" class="reference"><a href="#cite_note-merck-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> Its corrosive effect on skin and mucous membranes is due to a protein-degenerating effect.<sup id="cite_ref-U_51-2" class="reference"><a href="#cite_note-U-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Repeated or prolonged skin contact with phenol may cause <a href="/wiki/Dermatitis" title="Dermatitis">dermatitis</a>, or even second and third-degree burns.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> Inhalation of phenol vapor may cause lung <a href="/wiki/Edema" title="Edema">edema</a>.<sup id="cite_ref-merck_62-1" class="reference"><a href="#cite_note-merck-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> The substance may cause harmful effects on the central nervous system and heart, resulting in <a href="/wiki/Cardiac_dysrhythmia" class="mw-redirect" title="Cardiac dysrhythmia">dysrhythmia</a>, <a href="/wiki/Seizure" title="Seizure">seizures</a>, and <a href="/wiki/Coma" title="Coma">coma</a>.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Kidney" title="Kidney">kidneys</a> may be affected as well. Long-term or repeated exposure of the substance may have harmful effects on the <a href="/wiki/Liver" title="Liver">liver</a> and <a href="/wiki/Kidney" title="Kidney">kidneys</a>.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> There is no evidence that phenol causes <a href="/wiki/Cancer" title="Cancer">cancer</a> in humans.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> Besides its <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a> effects, another mechanism for the toxicity of phenol may be the formation of <a href="/wiki/Phenoxyl" class="mw-redirect" title="Phenoxyl">phenoxyl</a> <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">radicals</a>.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Since phenol is absorbed through the skin relatively quickly, systemic poisoning can occur in addition to the local caustic burns.<sup id="cite_ref-U_51-3" class="reference"><a href="#cite_note-U-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Resorptive poisoning by a large quantity of phenol can occur even with only a small area of skin, rapidly leading to paralysis of the central nervous system and a severe drop in body temperature. The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> for oral toxicity is less than 500 mg/kg for dogs, rabbits, or mice; the minimum lethal human dose was cited as 140 mg/kg.<sup id="cite_ref-U_51-4" class="reference"><a href="#cite_note-U-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> The Agency for Toxic Substances and Disease Registry (ATSDR), U.S. Department of Health and Human Services states the fatal dose for ingestion of phenol is from 1 to 32 g.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Chemical_burn" title="Chemical burn">Chemical burns</a> from <a href="/wiki/Human_skin" title="Human skin">skin</a> exposures can be decontaminated by washing with <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycol</a>,<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">isopropyl alcohol</a>,<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> or perhaps even copious amounts of water.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> Removal of contaminated clothing is required, as well as immediate <a href="/wiki/Hospital" title="Hospital">hospital</a> treatment for large splashes. This is particularly important if the phenol is mixed with <a href="/wiki/Phenol-chloroform_extraction" class="mw-redirect" title="Phenol-chloroform extraction">chloroform</a> (a commonly used mixture in molecular biology for <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a> purification).<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. (December 2023)">citation needed</span></a></i>]</sup> Phenol is also a reproductive toxin causing increased risk of miscarriage and low birth weight indicating retarded development in utero.<sup id="cite_ref-pubchem_5-5" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Shipping">Shipping</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=23" title="Edit section: Shipping"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenol, which is produced and hence transported in large volumes, is shipped in a molten state below 70 °C (158 °F). The melting point is lowered and corrosive nature enhanced in the presence of small amounts of water. Typically stainless steel containers and nitrogen-blanketing are required to prevent discoloration.<sup id="cite_ref-Ullmann_8-5" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Phenols">Phenols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=24" title="Edit section: Phenols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Phenols" title="Phenols">Phenols</a></div> <p>The word <i>phenol</i> is also used to refer to any compound that contains a six-membered <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> ring, bonded directly to a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> (-OH). Thus, phenols are a class of <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> of which the phenol discussed in this article is the simplest member. </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=Phenol&action=edit&section=25" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Bamberger_rearrangement" title="Bamberger rearrangement">Bamberger rearrangement</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Cresol" title="Cresol">Cresol</a></li> <li><a href="/wiki/Fries_rearrangement" title="Fries rearrangement">Fries rearrangement</a></li> <li><a href="/wiki/Polyphenol" title="Polyphenol">Polyphenol</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=Phenol&action=edit&section=26" 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 .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_1-0">^</a></b></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 class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 690. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. <q>Only one name is retained, phenol, for C<sub>6</sub>H<sub>5</sub>-OH, both as a preferred name and for general nomenclature.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Front+Matter&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=690&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-chemsrc-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-chemsrc_2-0">^</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.chemsrc.com/en/cas/108-95-2_1101388.html">"Phenol_msds"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Phenol_msds&rft_id=https%3A%2F%2Fwww.chemsrc.com%2Fen%2Fcas%2F108-95-2_1101388.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-PGCH-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-PGCH_3-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0493.html">"#0493"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230493&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0493.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKüttMovchunRodimaDansauer2008" class="citation journal cs1">Kütt, Agnes; Movchun, Valeria; Rodima, Toomas; et al. (2008). "Pentakis(trifluoromethyl)phenyl, a Sterically Crowded and Electron-withdrawing Group: Synthesis and Acidity of Pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline". <i>The Journal of Organic Chemistry</i>. <b>73</b> (7): <span class="nowrap">2607–</span>20. <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%2Fjo702513w">10.1021/jo702513w</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18324831">18324831</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Pentakis%28trifluoromethyl%29phenyl%2C+a+Sterically+Crowded+and+Electron-withdrawing+Group%3A+Synthesis+and+Acidity+of+Pentakis%28trifluoromethyl%29benzene%2C+-toluene%2C+-phenol%2C+and+-aniline&rft.volume=73&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2607-%3C%2Fspan%3E20&rft.date=2008&rft_id=info%3Adoi%2F10.1021%2Fjo702513w&rft_id=info%3Apmid%2F18324831&rft.aulast=K%C3%BCtt&rft.aufirst=Agnes&rft.au=Movchun%2C+Valeria&rft.au=Rodima%2C+Toomas&rft.au=Dansauer%2C+Timo&rft.au=Rusanov%2C+Eduard+B.&rft.au=Leito%2C+Ivo&rft.au=Kaljurand%2C+Ivari&rft.au=Koppel%2C+Juta&rft.au=Pihl%2C+Viljar&rft.au=Koppel%2C+Ivar&rft.au=Ovsjannikov%2C+Gea&rft.au=Toom%2C+Lauri&rft.au=Mishima%2C+Masaaki&rft.au=Medebielle%2C+Maurice&rft.au=Lork%2C+Enno&rft.au=R%C3%B6schenthaler%2C+Gerd-Volker&rft.au=Koppel%2C+Ilmar+A.&rft.au=Kolomeitsev%2C+Alexander+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-pubchem-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pubchem_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pubchem_5-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pubchem_5-5"><sup><i><b>f</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://pubchem.ncbi.nlm.nih.gov/compound/996">"Phenol"</a>. PubChem, US National Library of Medicine. 10 June 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">12 June</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Phenol&rft.pub=PubChem%2C+US+National+Library+of+Medicine&rft.date=2023-06-10&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F996&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-sigma-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sigma_6-2"><sup><i><b>c</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/sial/77608">Phenol</a>. Retrieved on 2022-02-15.</span> </li> <li id="cite_note-IDLH-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-IDLH_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IDLH_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IDLH_7-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/108952.html">"Phenol"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Phenol&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F108952.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_8-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ullmann_8-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Ullmann_8-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWeberWeberKleine-Boymann2004" class="citation encyclopaedia cs1">Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004). "Phenol". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <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.a19_299.pub3">10.1002/14356007.a19_299.pub3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Phenol&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2004&rft_id=info%3Adoi%2F10.1002%2F14356007.a19_299.pub3&rft.isbn=978-3-527-30673-2&rft.aulast=Weber&rft.aufirst=Manfred&rft.au=Weber%2C+Markus&rft.au=Kleine-Boymann%2C+Michael&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZvi_Rappoport2003" class="citation book cs1">Zvi Rappoport, ed. (2003). <i>The Chemistry of Phenols</i>. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. <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%2F0470857277">10.1002/0470857277</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470857274" title="Special:BookSources/9780470857274"><bdi>9780470857274</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Chemistry+of+Phenols&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pub=John+Wiley+%26+Sons&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2F0470857277&rft.isbn=9780470857274&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSmithMarch2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.aulast=Smith&rft.aufirst=Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><i>Organic Chemistry</i> 2nd Ed. 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Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCramer,_R._E.Bopp,_T._T.1977" class="citation journal cs1">Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". <i>Journal of Chemical Education</i>. <b>54</b>: <span class="nowrap">612–</span>613. <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%2Fed054p612">10.1021/ed054p612</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=Graphical+display+of+the+enthalpies+of+adduct+formation+for+Lewis+acids+and+bases&rft.volume=54&rft.pages=%3Cspan+class%3D%22nowrap%22%3E612-%3C%2Fspan%3E613&rft.date=1977&rft_id=info%3Adoi%2F10.1021%2Fed054p612&rft.au=Cramer%2C+R.+E.&rft.au=Bopp%2C+T.+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span> The plots shown in this paper used older parameters. Improved E&C parameters are listed in <a href="/wiki/ECW_model" title="ECW model">ECW model</a>.</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCapponiGutHellrungPersy1999" class="citation journal cs1">Capponi, Marco; Gut, Ivo G.; Hellrung, Bruno; Persy, Gaby; Wirz, Jakob (1999). "Ketonization equilibria of phenol in aqueous solution". <i><a href="/wiki/Canadian_Journal_of_Chemistry" title="Canadian Journal of Chemistry">Can. J. Chem.</a></i> <b>77</b> (<span class="nowrap">5–</span>6): <span class="nowrap">605–</span>613. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fcjc-77-5-6-605">10.1139/cjc-77-5-6-605</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Can.+J.+Chem.&rft.atitle=Ketonization+equilibria+of+phenol+in+aqueous+solution&rft.volume=77&rft.issue=%3Cspan+class%3D%22nowrap%22%3E5%E2%80%93%3C%2Fspan%3E6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E605-%3C%2Fspan%3E613&rft.date=1999&rft_id=info%3Adoi%2F10.1139%2Fcjc-77-5-6-605&rft.aulast=Capponi&rft.aufirst=Marco&rft.au=Gut%2C+Ivo+G.&rft.au=Hellrung%2C+Bruno&rft.au=Persy%2C+Gaby&rft.au=Wirz%2C+Jakob&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" 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 id="CITEREFClaydenGreevesWarrenWothers2001" class="citation book cs1"><a href="/wiki/Jonathan_Clayden" title="Jonathan Clayden">Clayden, Jonathan</a>; Greeves, Nick; <a href="/wiki/Stuart_Warren" title="Stuart Warren">Warren, Stuart</a>; <a href="/wiki/Peter_Wothers" title="Peter Wothers">Wothers, Peter</a> (2001). <i>Organic Chemistry</i> (1st ed.). Oxford University Press. p. 531. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-850346-0" title="Special:BookSources/978-0-19-850346-0"><bdi>978-0-19-850346-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=531&rft.edition=1st&rft.pub=Oxford+University+Press&rft.date=2001&rft.isbn=978-0-19-850346-0&rft.aulast=Clayden&rft.aufirst=Jonathan&rft.au=Greeves%2C+Nick&rft.au=Warren%2C+Stuart&rft.au=Wothers%2C+Peter&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" 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 id="CITEREFArnoldBuckley1949" class="citation journal cs1">Arnold, Richard T.; Buckley, Jay S. (1 May 1949). "The Dienone-Phenol Rearrangement. II. Rearrangement of 1-Keto-4-methyl-4-phenyl-1,4-dihydronaphthalene". <i>J. Am. Chem. 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Runge (1834) <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?id=wu.89048351654#page/308/mode/1up">"Ueber einige Produkte der Steinkohlendestillation,"</a> <i>Annalen der Physik und Chemie</i>, <b>31</b>: 308-328.</span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text">Auguste Laurent (1841) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k347443/f194.image">"Mémoire sur le phényle et ses dérivés"</a> (Memoir on benzene and its derivatives), <i>Annales de Chimie et de Physique</i>, series 3, <b>3</b>: 195-228. On page 198, Laurent names phenol "hydrate de phényle" and "l'acide phénique".</span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text">Auguste Laurent (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique," <i>Annales de Chemie et de Physique</i>, vol. 63, pp. 27–45, see <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Lx0AAAAAMAAJ&pg=PA44">p. 44</a>: Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage. (I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acid, because benzene is found in illuminating gas.)</span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text">Gerhardt, Charles (1843) <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?id=uva.x002489028;view=1up#page/215/mode/1up">"Recherches sur la salicine,"</a> <i>Annales de Chimie et de Physique</i>, series 3, <b>7</b>: 215-229. Gerhardt coins the name "phénol" on page 221.</span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLister1867" class="citation web cs1">Lister, Joseph (1867). <a rel="nofollow" class="external text" href="https://sourcebooks.fordham.edu/mod/1867lister.asp">"Antiseptic Principle Of The Practice Of Surgery"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Antiseptic+Principle+Of+The+Practice+Of+Surgery&rft.date=1867&rft.aulast=Lister&rft.aufirst=Joseph&rft_id=https%3A%2F%2Fsourcebooks.fordham.edu%2Fmod%2F1867lister.asp&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHollingham2008" class="citation book cs1">Hollingham, Richard (2008). <i>Blood and Guts: A History of Surgery</i>. 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BBC Books - Random House. p. 62. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781407024530" title="Special:BookSources/9781407024530"><bdi>9781407024530</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Blood+and+Guts%3A+A+History+of+Surgery&rft.pages=62&rft.pub=BBC+Books+-+Random+House&rft.date=2008&rft.isbn=9781407024530&rft.aulast=Hollingham&rft.aufirst=Richard&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-50">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHollingham2008" class="citation book cs1">Hollingham, Richard (2008). <i>Blood and Guts: A History of Surgery</i>. 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Vol. 25. Wiley-VCH. 2003. pp. <span class="nowrap">589–</span>604.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Phenol&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=%3Cspan+class%3D%22nowrap%22%3E589-%3C%2Fspan%3E604&rft.pub=Wiley-VCH&rft.date=2003&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-TysonNOVA-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-TysonNOVA_52-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.pbs.org/wgbh/nova/holocaust/experiside.html#pois"><i>The Experiments</i></a> by Peter Tyson. NOVA</span> </li> <li id="cite_note-NaziDrs-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-NaziDrs_53-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.holocaust-history.org/lifton/LiftonT254.shtml"><i>The Nazi Doctors</i></a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171022104811/http://www.holocaust-history.org/lifton/LiftonT254.shtml">Archived</a> 2017-10-22 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, Chapter 14, Killing with Syringes: Phenol Injections. By Dr. Robert Jay Lifton</span> </li> <li id="cite_note-carbolic-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-carbolic_54-0">^</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://web.archive.org/web/20061112224223/http://www.wsg-hist.uni-linz.ac.at/AUSCHWITZ/HTML/Phenol.html">"Killing through phenol injection"</a>. <i>Auschwitz: Final Station Extermination</i>. Linz, Austria: Johannes Kepler University. 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Deepa Ananth, Zoo's print journal, 15(5), pages 259-262 (<a rel="nofollow" class="external text" href="https://zoosprint.zooreach.org/ZooPrintJournal/2000/May/259-262.pdf">article</a>)</span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text">The Beaver: Its Life and Impact. 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Retrieved <span class="nowrap">8 August</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Bruichladdich&rft.atitle=Bruichladdich&rft_id=http%3A%2F%2Fwww.bruichladdich.com%2Fthe-whisky%2Foctomore&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-Juteau-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-Juteau_60-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJuteauCôtéDuckettBeaudet2005" class="citation journal cs1">Juteau, P.; Côté, V; Duckett, MF; Beaudet, R; Lépine, F; Villemur, R; Bisaillon, JG (2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1099%2Fijs.0.02914-0">"<i>Cryptanaerobacter phenolicus</i> gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate"</a>. <i>International Journal of Systematic and Evolutionary Microbiology</i>. <b>55</b> (Pt 1): <span class="nowrap">245–</span>50. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1099%2Fijs.0.02914-0">10.1099/ijs.0.02914-0</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15653882">15653882</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Systematic+and+Evolutionary+Microbiology&rft.atitle=Cryptanaerobacter+phenolicus+gen.+nov.%2C+sp.+nov.%2C+an+anaerobe+that+transforms+phenol+into+benzoate+via+4-hydroxybenzoate&rft.volume=55&rft.issue=Pt+1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E245-%3C%2Fspan%3E50&rft.date=2005&rft_id=info%3Adoi%2F10.1099%2Fijs.0.02914-0&rft_id=info%3Apmid%2F15653882&rft.aulast=Juteau&rft.aufirst=P.&rft.au=C%C3%B4t%C3%A9%2C+V&rft.au=Duckett%2C+MF&rft.au=Beaudet%2C+R&rft.au=L%C3%A9pine%2C+F&rft.au=Villemur%2C+R&rft.au=Bisaillon%2C+JG&rft_id=https%3A%2F%2Fdoi.org%2F10.1099%252Fijs.0.02914-0&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRehfussUrban2005" class="citation journal cs1">Rehfuss, Marc; Urban, James (2005). "<i>Rhodococcus phenolicus</i> sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene, dichlorobenzene and phenol as sole carbon sources". <i>Systematic and Applied Microbiology</i>. <b>28</b> (8): <span class="nowrap">695–</span>701. <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/2005SyApM..28..695R">2005SyApM..28..695R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.syapm.2005.05.011">10.1016/j.syapm.2005.05.011</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16261859">16261859</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Systematic+and+Applied+Microbiology&rft.atitle=Rhodococcus+phenolicus+sp.+nov.%2C+a+novel+bioprocessor+isolated+actinomycete+with+the+ability+to+degrade+chlorobenzene%2C+dichlorobenzene+and+phenol+as+sole+carbon+sources&rft.volume=28&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E695-%3C%2Fspan%3E701&rft.date=2005&rft_id=info%3Apmid%2F16261859&rft_id=info%3Adoi%2F10.1016%2Fj.syapm.2005.05.011&rft_id=info%3Abibcode%2F2005SyApM..28..695R&rft.aulast=Rehfuss&rft.aufirst=Marc&rft.au=Urban%2C+James&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> <li id="cite_note-merck-62"><span class="mw-cite-backlink">^ <a href="#cite_ref-merck_62-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-merck_62-1"><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="CITEREFBudavari1996" class="citation book cs1">Budavari, S, ed. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicol+Appl+Pharmacol&rft.atitle=Decontamination+of+the+skin+of+swine+following+phenol+exposure%3A+a+comparison+of+the+relative+efficacy+of+water+versus+polyethylene+glycol%2Findustrial+methylated+spirits&rft.volume=43&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E199-%3C%2Fspan%3E206&rft.date=1978&rft_id=info%3Apmid%2F625760&rft_id=info%3Adoi%2F10.1016%2FS0041-008X%2878%2980044-1&rft_id=info%3Abibcode%2F1978ToxAP..43..199P&rft.aulast=Pullin&rft.aufirst=TG&rft.au=Pinkerton%2C+MN&rft.au=Johnston%2C+RV&rft.au=Kilian%2C+DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenol" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenol&action=edit&section=27" title="Edit section: External 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class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/34px-Wikiquote-logo.svg.png" decoding="async" width="34" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/51px-Wikiquote-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikiquote-logo.svg/68px-Wikiquote-logo.svg.png 2x" data-file-width="300" data-file-height="355" /></a></span></div> <div class="side-box-text plainlist">Wikiquote has quotations related to <i><b><a href="https://en.wikiquote.org/wiki/Special:Search/Phenol" class="extiw" title="q:Special:Search/Phenol">Phenol</a></b></i>.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735" /><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" 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href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Carbolic_Acid" class="extiw" title="wikisource:1911 Encyclopædia Britannica/Carbolic Acid">Carbolic Acid</a></span>".</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0070.htm">International Chemical Safety Card 0070</a></li> <li><a rel="nofollow" class="external text" href="https://hazard.com//msds/mf/baker/baker/files/p1949.htm">Phenol Material Safety Data Sheet</a></li> <li><a rel="nofollow" class="external text" href="http://www.npi.gov.au/resource/phenol">National Pollutant Inventory: Phenol Fact Sheet</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0493.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/topics/phenol/">CDC - Phenol - NIOSH Workplace Safety and Health Topic</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20051012222001/http://www-cie.iarc.fr/htdocs/monographs/vol71/027-phenol.html">IARC Monograph: "Phenol"</a></li> <li><a rel="nofollow" class="external text" href="http://tenwatts.blogspot.com/2007/08/phenol-edison-bayer-and-records.html">Arcane Radio Trivia outlines competing uses for Phenol circa 1915</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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 ul,.mw-parser-output .hlist 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href="/wiki/Euflavine" title="Euflavine">Euflavine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biguanide" title="Biguanide">Biguanides</a> and <a href="/wiki/Amidine" title="Amidine">amidines</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/Dibrompropamidine" title="Dibrompropamidine">Dibrompropamidine</a></li> <li><a href="/wiki/Chlorhexidine" title="Chlorhexidine">Chlorhexidine</a><sup>#</sup></li> <li><a href="/wiki/Propamidine" title="Propamidine">Propamidine</a></li> <li><a href="/wiki/Hexamidine" title="Hexamidine">Hexamidine</a></li> <li><a href="/wiki/Polyhexanide" title="Polyhexanide">Polihexanide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Phenol</a> and derivatives</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/Hexachlorophene" title="Hexachlorophene">Hexachlorophene</a></li> <li><a href="/wiki/Policresulen" title="Policresulen">Policresulen</a></li> <li><a class="mw-selflink selflink">Phenol</a></li> <li><a href="/wiki/Triclosan" title="Triclosan">Triclosan</a></li> <li><a href="/wiki/Triclocarban" title="Triclocarban">Triclocarban</a></li> <li><a href="/wiki/Chloroxylenol" title="Chloroxylenol">Chloroxylenol</a><sup>#</sup></li> <li><a href="/wiki/Biphenylol" class="mw-redirect" title="Biphenylol">Biphenylol</a></li> <li><a href="/wiki/Fenticlor" title="Fenticlor">Fenticlor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrofuran" title="Nitrofuran">Nitrofuran</a> derivatives</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/Nitrofurazone" title="Nitrofurazone">Nitrofurazone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Iodine" title="Iodine">Iodine</a> products</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/Iodine/octylphenoxypolyglycolether" class="mw-redirect" title="Iodine/octylphenoxypolyglycolether">Iodine/octylphenoxypolyglycolether</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a><sup>#</sup></li> <li><a href="/wiki/Diiodohydroxypropane" title="Diiodohydroxypropane">Diiodohydroxypropane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinoline" title="Quinoline">Quinoline</a> derivatives</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/Dequalinium" title="Dequalinium">Dequalinium</a></li> <li><a href="/wiki/Chlorquinaldol" title="Chlorquinaldol">Chlorquinaldol</a></li> <li><a href="/wiki/Oxyquinoline" class="mw-redirect" title="Oxyquinoline">Oxyquinoline</a></li> <li><a href="/wiki/Clioquinol" title="Clioquinol">Clioquinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quaternary_ammonium_compounds" class="mw-redirect" title="Quaternary ammonium compounds">Quaternary ammonium compounds</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/Benzalkonium_chloride" title="Benzalkonium chloride">Benzalkonium</a></li> <li><a href="/wiki/Benzethonium_chloride" title="Benzethonium chloride">Benzethonium chloride</a></li> <li><a href="/wiki/Cetrimonium" title="Cetrimonium">Cetrimonium</a> (<a href="/wiki/Cetrimonium_bromide" title="Cetrimonium bromide">bromide</a>/<a href="/wiki/Cetrimonium_chloride" title="Cetrimonium chloride">chloride</a>)</li> <li><a href="/wiki/Cetylpyridinium_chloride" title="Cetylpyridinium chloride">Cetylpyridinium</a></li> <li><a href="/wiki/Cetrimide" title="Cetrimide">Cetrimide</a></li> <li><a href="/wiki/Benzoxonium_chloride" title="Benzoxonium chloride">Benzoxonium chloride</a></li> <li><a href="/wiki/Didecyldimethylammonium_chloride" title="Didecyldimethylammonium chloride">Didecyldimethylammonium chloride</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mercury_(element)" title="Mercury (element)">Mercurial</a> products</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/Mercuric_amidochloride" title="Mercuric amidochloride">Mercuric amidochloride</a></li> <li><a href="/wiki/Phenylmercuric_borate" title="Phenylmercuric borate">Phenylmercuric borate</a></li> <li><a href="/wiki/Mercury(II)_chloride" title="Mercury(II) chloride">Mercuric chloride</a></li> <li><a href="/wiki/Merbromin" title="Merbromin">Merbromin</a></li> <li><a href="/wiki/Nitromersol" title="Nitromersol">Nitromersol</a></li> <li><a href="/wiki/Thiomersal" title="Thiomersal">Thiomersal</a></li> <li><a href="/wiki/Mercury(II)_iodide" title="Mercury(II) iodide">Mercuric iodide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silver" title="Silver">Silver</a> compounds</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/Silver_nitrate" title="Silver nitrate">Silver nitrate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohols_in_medicine" class="mw-redirect" title="Alcohols in medicine">Alcohols</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/1-Propanol" title="1-Propanol">Propanol (propyl alcohol)</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropanol (isopropyl alcohol)</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol (ethyl alcohol)</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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/Potassium_permanganate" title="Potassium permanganate">Potassium permanganate</a></li> <li><a href="/wiki/Sodium_hypochlorite" title="Sodium hypochlorite">Sodium hypochlorite</a></li> <li><a href="/wiki/Halazone" title="Halazone">Halazone</a></li> <li><a href="/wiki/Monalazone" title="Monalazone">Monalazone</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Eosin" title="Eosin">Eosin</a></li> <li><a href="/wiki/Chloramine-T" title="Chloramine-T">Chloramine-T (tosylchloramide)</a></li> <li><a href="/wiki/Octenidine_dihydrochloride" title="Octenidine dihydrochloride">Octenidine dihydrochloride</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></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="Throat_preparations_(R02)116" 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:Throat_preparations" title="Template:Throat preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Throat_preparations" title="Template talk:Throat preparations"><abbr title="Discuss this 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chloride">Benzalkonium</a></li> <li><a href="/wiki/Benzethonium_chloride" title="Benzethonium chloride">Benzethonium</a></li> <li><a href="/wiki/Cetrimonium" title="Cetrimonium">Cetrimonium</a> (<a href="/wiki/Cetrimonium_bromide" title="Cetrimonium bromide">bromide</a>/<a href="/wiki/Cetrimonium_chloride" title="Cetrimonium chloride">chloride</a>)</li> <li><a href="/wiki/Cetylpyridinium_chloride" title="Cetylpyridinium chloride">Cetylpyridinium</a></li> <li><a href="/wiki/Chlorhexidine" title="Chlorhexidine">Chlorhexidine</a></li> <li><a href="/wiki/Chlorquinaldol" title="Chlorquinaldol">Chlorquinaldol</a></li> <li><a href="/wiki/Dequalinium" title="Dequalinium">Dequalinium</a></li> <li><a href="/wiki/2,4-Dichlorobenzyl_alcohol" title="2,4-Dichlorobenzyl alcohol">Dichlorobenzyl alcohol</a></li> <li><a href="/wiki/Hexamidine" title="Hexamidine">Hexamidine</a></li> <li><a href="/wiki/Hexetidine" title="Hexetidine">Hexetidine</a></li> <li><a href="/wiki/Hexylresorcinol" 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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></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Phenol"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4346494-4">Germany</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" 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