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href="#Reactions_and_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reactions and uses</span> </div> </a> <button aria-controls="toc-Reactions_and_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 Reactions and uses subsection</span> </button> <ul id="toc-Reactions_and_uses-sublist" class="vector-toc-list"> <li id="toc-Li_biphenyl_radical" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Li_biphenyl_radical"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Li biphenyl radical</span> </div> </a> <ul id="toc-Li_biphenyl_radical-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Stereochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Stereochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Stereochemistry</span> </div> </a> <ul id="toc-Stereochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biphenyl_compounds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biphenyl_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biphenyl compounds</span> </div> </a> <ul id="toc-Biphenyl_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety_and_bioactivity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety_and_bioactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Safety and bioactivity</span> </div> </a> <ul id="toc-Safety_and_bioactivity-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">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-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">9</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" > <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 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Available in 36 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-36" 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">36 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AB%D9%86%D8%A7%D8%A6%D9%8A_%D8%A7%D9%84%D9%81%D9%8A%D9%86%D9%8A%D9%84" title="ثنائي الفينيل – Arabic" lang="ar" hreflang="ar" data-title="ثنائي الفينيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/%C3%87oxn%C3%BCv%C9%99li_aromatik_birl%C9%99%C5%9Fm%C9%99l%C9%99r" title="Çoxnüvəli aromatik birləşmələr – Azerbaijani" lang="az" hreflang="az" data-title="Çoxnüvəli aromatik birləşmələr" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AC%E0%A6%BE%E0%A6%87%E0%A6%AB%E0%A6%BF%E0%A6%A8%E0%A6%BE%E0%A6%87%E0%A6%B2" title="বাইফিনাইল – Bangla" lang="bn" hreflang="bn" data-title="বাইফিনাইল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Bifenil" title="Bifenil – Catalan" lang="ca" hreflang="ca" data-title="Bifenil" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Bifenyl" title="Bifenyl – Czech" lang="cs" hreflang="cs" data-title="Bifenyl" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Biphenyl" title="Biphenyl – German" lang="de" hreflang="de" data-title="Biphenyl" 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/Bifen%C3%BC%C3%BCl" title="Bifenüül – Estonian" lang="et" hreflang="et" data-title="Bifenüül" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Bifenilo" title="Bifenilo – Spanish" lang="es" hreflang="es" data-title="Bifenilo" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Bifenilo" title="Bifenilo – Basque" lang="eu" hreflang="eu" data-title="Bifenilo" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%DB%8C%E2%80%8C%D9%81%D9%86%DB%8C%D9%84" title="بی‌فنیل – Persian" lang="fa" hreflang="fa" data-title="بی‌فنیل" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Biph%C3%A9nyle" title="Biphényle – French" lang="fr" hreflang="fr" data-title="Biphényle" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B0%94%EC%9D%B4%ED%8E%98%EB%8B%90" title="바이페닐 – Korean" lang="ko" hreflang="ko" data-title="바이페닐" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B4%D5%AB%D6%86%D5%A5%D5%B6%D5%AB%D5%AC" title="Դիֆենիլ – Armenian" lang="hy" hreflang="hy" data-title="Դիֆենիլ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AC%E0%A4%BE%E0%A4%87%E0%A4%AB%E0%A4%BF%E0%A4%A8%E0%A4%BE%E0%A4%87%E0%A4%B2" title="बाइफिनाइल – Hindi" lang="hi" hreflang="hi" data-title="बाइफिनाइल" 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/Bifenil" title="Bifenil – Croatian" lang="hr" hreflang="hr" data-title="Bifenil" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Bifenile" title="Bifenile – Italian" lang="it" hreflang="it" data-title="Bifenile" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%91%E1%83%98%E1%83%A4%E1%83%94%E1%83%9C%E1%83%98%E1%83%9A%E1%83%98" title="ბიფენილი – Georgian" lang="ka" hreflang="ka" data-title="ბიფენილი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%91%D0%B8%D1%84%D0%B5%D0%BD%D0%B8%D0%BB" title="Бифенил – Kazakh" lang="kk" hreflang="kk" data-title="Бифенил" 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%94%D0%B8%D1%84%D0%B5%D0%BD%D0%B8%D0%BB" title="Дифенил – Kyrgyz" lang="ky" hreflang="ky" data-title="Дифенил" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Bifenils" title="Bifenils – Latvian" lang="lv" hreflang="lv" data-title="Bifenils" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Bifenil" title="Bifenil – Hungarian" lang="hu" hreflang="hu" data-title="Bifenil" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Bifenyl" title="Bifenyl – Dutch" lang="nl" hreflang="nl" data-title="Bifenyl" 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%93%E3%83%95%E3%82%A7%E3%83%8B%E3%83%AB" title="ビフェニル – Japanese" lang="ja" hreflang="ja" data-title="ビフェニル" 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/Bifenyl" title="Bifenyl – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Bifenyl" 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/Difenil" title="Difenil – Uzbek" lang="uz" hreflang="uz" data-title="Difenil" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Bifenyl" title="Bifenyl – Polish" lang="pl" hreflang="pl" data-title="Bifenyl" 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/Bifenilo" title="Bifenilo – Portuguese" lang="pt" hreflang="pt" data-title="Bifenilo" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Bifenil" title="Bifenil – Romanian" lang="ro" hreflang="ro" data-title="Bifenil" 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%94%D0%B8%D1%84%D0%B5%D0%BD%D0%B8%D0%BB" title="Дифенил – Russian" lang="ru" hreflang="ru" data-title="Дифенил" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Bifenyl" title="Bifenyl – Slovak" lang="sk" hreflang="sk" data-title="Bifenyl" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Bifenil" title="Bifenil – Serbian" lang="sr" hreflang="sr" data-title="Bifenil" 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/Bifenil" title="Bifenil – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Bifenil" 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/Bifenyyli" title="Bifenyyli – Finnish" lang="fi" hreflang="fi" data-title="Bifenyyli" 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/Difenyl" title="Difenyl – Swedish" lang="sv" hreflang="sv" data-title="Difenyl" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D0%B8%D1%84%D0%B5%D0%BD%D1%96%D0%BB" title="Дифеніл – Ukrainian" lang="uk" hreflang="uk" data-title="Дифеніл" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%81%94%E8%8B%AF" title="联苯 – Chinese" lang="zh" hreflang="zh" data-title="联苯" 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/Q410915#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> 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</nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button 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"><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">For the compound including hydroxyl groups, see <a href="/wiki/Bisphenol" title="Bisphenol">Bisphenol</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Lemonene" redirects here. For the monoterpene in citrus oil, see <a href="/wiki/Limonene" title="Limonene">Limonene</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Biphenyl </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Bifenyl.svg" class="mw-file-description" title="Skeletal formula"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Bifenyl.svg/220px-Bifenyl.svg.png" decoding="async" width="220" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Bifenyl.svg/330px-Bifenyl.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Bifenyl.svg/440px-Bifenyl.svg.png 2x" data-file-width="1032" data-file-height="369" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Biphenyl-3D-vdW.png" class="mw-file-description" title="Space filling model showing its twisted conformation"><img alt="Space filling model showing its twisted conformation" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Biphenyl-3D-vdW.png/200px-Biphenyl-3D-vdW.png" decoding="async" width="200" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Biphenyl-3D-vdW.png/300px-Biphenyl-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Biphenyl-3D-vdW.png/400px-Biphenyl-3D-vdW.png 2x" data-file-width="1000" data-file-height="788" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:BiphenylSample.jpg" class="mw-file-description" title="sample"><img alt="sample" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/BiphenylSample.jpg/200px-BiphenylSample.jpg" decoding="async" width="200" height="185" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/BiphenylSample.jpg/300px-BiphenylSample.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/BiphenylSample.jpg/400px-BiphenylSample.jpg 2x" data-file-width="1499" data-file-height="1388" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/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;">1,1′-Biphenyl</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>Biphenyl</li><li>Phenylbenzene</li><li>Xenene</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=92-52-4">92-52-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccccc1-c2ccccc2">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00985">B00985</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1634058 </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=17097">CHEBI:17097</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL14092">ChEMBL14092</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.6828.html">6828</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/100.001.967">100.001.967</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410915#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>202-163-5</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E230 <a href="/wiki/E_number#E200–E299" title="E number">(preservatives)</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>3808 </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/C06588">C06588</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/7095">7095</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>DU8050000</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/2L9GJK6MGN">2L9GJK6MGN</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>3077 </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/DTXSID4020161">DTXSID4020161</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410915#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZUOUZKKEUPVFJK-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/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZUOUZKKEUPVFJK-UHFFFAOYAV</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">c1ccccc1-c2ccccc2</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>12</sub><span title="Hydrogen">H</span><sub>10</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002154212000000000♠"></span>154.212</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless to pale-yellow crystals </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>pleasant<sup id="cite_ref-PGCH_1-0" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.04 g/cm<sup>3</sup><sup id="cite_ref-GESTIS_2-0" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>69.2 °C (156.6 °F; 342.3 K)<sup id="cite_ref-GESTIS_2-2" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>255 °C (491 °F; 528 K)<sup id="cite_ref-GESTIS_2-3" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<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/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>4.45 mg/L<sup id="cite_ref-GESTIS_2-1" class="reference"><a href="#cite_note-GESTIS-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>0.005 mmHg (20°C)<sup id="cite_ref-PGCH_1-1" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−103.25·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr> </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="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</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="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </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_811dcee2cbfc5fb2" /></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>113 °C (235 °F; 386 K)<sup id="cite_ref-GESTIS_2-4" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>540 °C (1,004 °F; 813 K)<sup id="cite_ref-GESTIS_2-5" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>0.6–5.8%<sup id="cite_ref-PGCH_1-2" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>2400 mg/kg (oral, rabbit)<br />3280 mg/kg (oral, rat)<br />1900 mg/kg (oral, mouse)<br />2400 mg/kg (oral, rat)<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 1 mg/m<sup>3</sup> (0.2 ppm)<sup id="cite_ref-PGCH_1-3" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<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>TWA 1 mg/m<sup>3</sup> (0.2 ppm)<sup id="cite_ref-PGCH_1-4" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>100 mg/m<sup>3</sup><sup id="cite_ref-PGCH_1-5" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443423597&page2=Biphenyl">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>Biphenyl</b> (also known as <b>diphenyl</b>, <b>phenylbenzene</b>, <b>1,1′-biphenyl</b>, <b>lemonene</b><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> or <b>BP</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> that forms colorless crystals. Particularly in older literature, compounds containing the <a href="/wiki/Functional_group" title="Functional group">functional group</a> consisting of biphenyl less one hydrogen (the site at which it is attached) may use the prefixes <b>xenyl</b> or <b>diphenylyl</b>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>It has a distinctively pleasant smell. Biphenyl is an <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbon</a> with a <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>. It is notable as a starting material for the production of <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">polychlorinated biphenyls</a> (PCBs), which were once widely used as <a href="/wiki/Dielectric" title="Dielectric">dielectric</a> fluids and <a href="/wiki/Heat_transfer" title="Heat transfer">heat transfer</a> agents. </p><p>Biphenyl is also an intermediate for the production of a host of other <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> such as <a href="/wiki/Emulsifier" class="mw-redirect" title="Emulsifier">emulsifiers</a>, <a href="/wiki/Optical_brightener" title="Optical brightener">optical brighteners</a>, <a href="/wiki/Fungicide" title="Fungicide">crop protection</a> products, and <a href="/wiki/Plastic" title="Plastic">plastics</a>. Biphenyl is <a href="/wiki/Solubility" title="Solubility">insoluble</a> in water, but soluble in typical <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>. The biphenyl molecule consists of two connected <a href="/wiki/Phenyl_ring" class="mw-redirect" title="Phenyl ring">phenyl rings</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties_and_occurrence">Properties and occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=1" title="Edit section: Properties and occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Biphenyl is a solid at room temperature, with a melting point of 69.2 °C (156.6 °F). In the gas phase the molecule exists in two <a href="/wiki/Enantiomorphic" class="mw-redirect" title="Enantiomorphic">enantiomorphic</a> twisted forms with an angle between the planes of the two rings of 44.4°. In the room-temperature solid, biphenyl is crystalline with <a href="/wiki/Space_group" title="Space group">space group</a> P2<sub>1</sub>/c, which does not allow for <a href="/wiki/Chiral" class="mw-redirect" title="Chiral">chiral</a> crystals. Rather than there being a <a href="/wiki/Double-well_potential" title="Double-well potential">double-well potential</a> entailing the two twisted conformations, the potential energy is minimized at zero twist.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Biphenyl occurs naturally in <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>, <a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">crude oil</a>, and <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a> and can be isolated from these sources via <a href="/wiki/Distillation" title="Distillation">distillation</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is produced industrially as a byproduct of the dealkylation of <a href="/wiki/Toluene" title="Toluene">toluene</a> to produce <a href="/wiki/Methane" title="Methane">methane</a>: </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">3</sub> + C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub> → C<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> + CH<sub class="template-chem2-sub">4</sub></span></dd></dl> <p>The other principal route is by the <a href="/wiki/Scholl_reaction" title="Scholl reaction">oxidative dehydrogenation</a> of <a href="/wiki/Benzene" title="Benzene">benzene</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub> + ½ O<sub class="template-chem2-sub">2</sub> → C<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> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Annually 40,000,000 kg are produced by these routes.<sup id="cite_ref-Ullmanns_9-0" class="reference"><a href="#cite_note-Ullmanns-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>In the laboratory, biphenyl can also be synthesized by treating <a href="/wiki/Phenylmagnesium_bromide" title="Phenylmagnesium bromide">phenylmagnesium bromide</a> with copper(II) salts. </p><p>It can also be prepared using <a href="/wiki/Diazonium_compound" title="Diazonium compound">diazonium salts</a>. When <a href="/wiki/Aniline" title="Aniline">aniline</a> is treated with NaNO<sub>2</sub>+dilute HCl at 5°C, it yields benzene diazonium chloride. When this is further reacted with benzene, biphenyl is formed. This is known as the <a href="/wiki/Gomberg%E2%80%93Bachmann_reaction" title="Gomberg–Bachmann reaction">Gomberg–Bachmann reaction</a>. </p><p><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Ph-NH2->[{\text{NaNO}}_{2}{\text{(aq), HCl}}][T{\text{=273-278K}}]Ph-N2+->[{\text{Ph-H, Δ}}]Ph-Ph}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mi>T</mi> <mrow class="MJX-TeXAtom-ORD"> <mtext>=273-278K</mtext> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>NaNO</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>(aq), HCl</mtext> </mrow> </mpadded> </munderover> </mrow> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>N</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ph-H, Δ</mtext> </mrow> </mpadded> </mover> </mrow> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Ph</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Ph-NH2->[{\text{NaNO}}_{2}{\text{(aq), HCl}}][T{\text{=273-278K}}]Ph-N2+->[{\text{Ph-H, Δ}}]Ph-Ph}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e967b1efa92a4e8fedb8b83b1bae2c4666216da4" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.808ex; margin-top: -0.346ex; margin-bottom: -0.53ex; width:48.45ex; height:6.009ex;" alt="{\displaystyle {\ce {Ph-NH2->[{\text{NaNO}}_{2}{\text{(aq), HCl}}][T{\text{=273-278K}}]Ph-N2+->[{\text{Ph-H, Δ}}]Ph-Ph}}}"></span> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions_and_uses">Reactions and uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=2" title="Edit section: Reactions and uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacking functional groups, biphenyl is fairly non-reactive, which is the basis of its main application: in a <a href="/wiki/Eutectic_mixture" class="mw-redirect" title="Eutectic mixture">eutectic mixture</a> with <a href="/wiki/Diphenyl_ether" title="Diphenyl ether">diphenyl ether</a>, as a heat transfer agent. This mixture is stable to 400 °C.<sup id="cite_ref-Ullmanns_9-1" class="reference"><a href="#cite_note-Ullmanns-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Biphenyl does undergo <a href="/wiki/Sulfonation" class="mw-redirect" title="Sulfonation">sulfonation</a> which, followed by base hydrolysis, produces <i>p</i>-hydroxybiphenyl and <i>p</i>,<i>p</i>′-dihydroxybiphenyl, which are useful fungicides. In other <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">substitution</a> reactions, it undergoes halogenation. <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">Polychlorinated biphenyls</a> were once popular pesticides.<sup id="cite_ref-Ullmanns_9-2" class="reference"><a href="#cite_note-Ullmanns-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Li_biphenyl_radical">Li biphenyl radical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=3" title="Edit section: Li biphenyl radical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lithium biphenyl contains the <a href="/wiki/Radical_anion" title="Radical anion">radical anion</a>, which is highly reducing (-3.1 V vs Fc<sup>+/0</sup>). Several solvates of alkali metal salts of biphenyl anion have been characterized by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>.<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> These salts, usually prepared in situ, are versatile reducing agents.<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> Lithium biphenyl offers some advantages relative to the related <a href="/wiki/Sodium_naphthalene" title="Sodium naphthalene">lithium naphthene</a>.<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> Related to Li/biphenyl is the derivative with <i>tert</i>-butyl groups on the biphenyl.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Stereochemistry">Stereochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=4" title="Edit section: Stereochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Rotation about the single bond in biphenyl, and especially its <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">ortho-substituted</a> derivatives, is <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">sterically hindered</a>. For this reason, some substituted biphenyls show <a href="/wiki/Atropisomerism" class="mw-redirect" title="Atropisomerism">atropisomerism</a>; that is, the individual C<sub>2</sub>-<a href="/wiki/Symmetry_group" title="Symmetry group">symmetric</a>-isomers are <a href="/wiki/Optical_rotation" title="Optical rotation">optically stable</a>. Some derivatives, as well as related molecules such as <a href="/wiki/BINAP" title="BINAP">BINAP</a>, find application as <a href="/wiki/Ligand" title="Ligand">ligands</a> in <a href="/wiki/Asymmetric_synthesis" class="mw-redirect" title="Asymmetric synthesis">asymmetric synthesis</a>. In the case of unsubstituted biphenyl, the equilibrium torsional angle is 44.4° and the torsional barriers are quite small, 6.0 kJ/mol at 0° and 6.5 kJ/mol at 90°.<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> Adding ortho substituents greatly increases the barrier: in the case of the 2,2'-dimethyl derivative, the barrier is 17.4 kcal/mol (72.8 kJ/mol).<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biphenyl_compounds">Biphenyl compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=5" title="Edit section: Biphenyl compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Substituted biphenyls have many uses. They are prepared by various <a href="/wiki/Coupling_reaction" title="Coupling reaction">coupling reactions</a> including the <a href="/wiki/Suzuki-Miyaura_reaction" class="mw-redirect" title="Suzuki-Miyaura reaction">Suzuki-Miyaura reaction</a> and the <a href="/wiki/Ullmann_reaction" title="Ullmann reaction">Ullmann reaction</a>. <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">Polychlorinated biphenyls</a> were once used as cooling and insulating fluids and <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">polybrominated biphenyls</a> are <a href="/wiki/Flame_retardant" title="Flame retardant">flame retardants</a>. The biphenyl motif also appears in <a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">drugs</a> such as <a href="/wiki/Diflunisal" title="Diflunisal">diflunisal</a> and <a href="/wiki/Telmisartan" title="Telmisartan">telmisartan</a>. The abbreviation <b>E7</b> stands for a <a href="/wiki/Liquid_crystal" title="Liquid crystal">liquid crystal</a> mixture consisting of several cyanobiphenyls with long aliphatic tails used commercially in <a href="/wiki/Liquid_crystal_display" class="mw-redirect" title="Liquid crystal display">liquid crystal displays</a> (<a href="/wiki/5CB" class="mw-redirect" title="5CB">5CB</a>, <a href="/w/index.php?title=7CB&action=edit&redlink=1" class="new" title="7CB (page does not exist)">7CB</a>, <a href="/w/index.php?title=8OCB&action=edit&redlink=1" class="new" title="8OCB (page does not exist)">8OCB</a> and <a href="/w/index.php?title=5CT&action=edit&redlink=1" class="new" title="5CT (page does not exist)">5CT</a><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>). A variety of <a href="/wiki/Benzidine" title="Benzidine">benzidine</a> derivatives are used in dyes and polymers. Research into biphenyl liquid crystal candidates mainly focuses on molecules with highly polar heads (for example cyano or halide groups) and aliphatic tails. It is part of the active group in the antibiotic <a href="/wiki/Oritavancin" title="Oritavancin">oritavancin</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Safety_and_bioactivity">Safety and bioactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=6" title="Edit section: Safety and bioactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Biphenyl prevents the growth of <a href="/wiki/Mold_(fungus)" class="mw-redirect" title="Mold (fungus)">molds</a> and <a href="/wiki/Fungus" title="Fungus">fungus</a>, and is therefore used as a <a href="/wiki/Preservative" title="Preservative">preservative</a> (<a href="/wiki/E_number" title="E number">E230</a>, in combination with E231, E232 and E233), particularly in the preservation of <a href="/wiki/Citrus" title="Citrus">citrus</a> fruits during transportation. It is no longer approved as a food additive in the European Union. </p><p>Biphenyl is mildly toxic, but can be degraded biologically by conversion into nontoxic compounds. Some <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> are able to hydroxylate biphenyl and its <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">polychlorinated biphenyls</a> (PCBs).<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> <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=Biphenyl&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a>, where the rings are fused</li> <li><a href="/wiki/Terphenyl" title="Terphenyl">Terphenyl</a>, three ringed analog</li> <li><a href="/wiki/Bithiophene" class="mw-redirect" title="Bithiophene">Bithiophene</a></li> <li><a href="/wiki/Polypyrrole" title="Polypyrrole">Polypyrrole</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=8" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-PGCH-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-PGCH_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-PGCH_1-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output 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href="#cite_ref-GESTIS_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GESTIS_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GESTIS_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GESTIS_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GESTIS_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-GESTIS_2-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=013450&lang=en">Record </a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a> </span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/92524.html">"Diphenyl"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. 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US <a href="/wiki/National_Institute_of_Standards_and_Technology" title="National Institute of Standards and Technology">National Institute of Standards and Technology</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=NIST+Chemistry+WebBook&rft.atitle=Biphenyl&rft_id=https%3A%2F%2Fwebbook.nist.gov%2Fcgi%2Fcbook.cgi%3FID%3D92-52-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABiphenyl" class="Z3988"></span> An obscure name, according to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.acs.org/molecule-of-the-week/archive/l/limonene.html">"Limonene"</a>. <i>Molecule of the Week Archive</i>. <a href="/wiki/American_Chemical_Society" title="American Chemical Society">American Chemical Society</a>. 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Theory Comput</i>. <b>4</b> (9): 1460–1471. <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%2Fct800182e">10.1021/ct800182e</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/26621432">26621432</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Theory+Comput.&rft.atitle=Torsional+Barriers+and+Equilibrium+Angle+of+Biphenyl%3A+Reconciling+Theory+with+Experiment&rft.volume=4&rft.issue=9&rft.pages=1460-1471&rft.date=2008&rft_id=info%3Adoi%2F10.1021%2Fct800182e&rft_id=info%3Apmid%2F26621432&rft.au=Mikael+P.+Johansson+and+Jeppe+Olsen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABiphenyl" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFB._Testa1982" class="citation book cs1">B. Testa (1982). "The geometry of molecules: basic principles and nomenclatures". In Christoph Tamm (ed.). <i>Stereochemistry</i>. Elsevier. p. 18.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+geometry+of+molecules%3A+basic+principles+and+nomenclatures&rft.btitle=Stereochemistry&rft.pages=18&rft.pub=Elsevier&rft.date=1982&rft.au=B.+Testa&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABiphenyl" 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="CITEREFMouquinhoSaavedraMaiauPetrova2011" class="citation journal cs1">Mouquinho, Ana; Saavedra, Mara; Maiau, Alexandre; Petrova, Krasimira; Barros, M. Teresa; Figueirinhas, J. L.; Sotomayor, João (30 June 2011). "Films Based on New Methacrylate Monomers: Synthesis, Characterisation and Electro-Optical Properties". <i>Molecular Crystals and Liquid Crystals</i>. <b>542</b> (1): 132/[654]–140/[662]. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F15421406.2011.570154">10.1080/15421406.2011.570154</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:97514765">97514765</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Crystals+and+Liquid+Crystals&rft.atitle=Films+Based+on+New+Methacrylate+Monomers%3A+Synthesis%2C+Characterisation+and+Electro-Optical+Properties&rft.volume=542&rft.issue=1&rft.pages=132%2F654-140%2F662&rft.date=2011-06-30&rft_id=info%3Adoi%2F10.1080%2F15421406.2011.570154&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A97514765%23id-name%3DS2CID&rft.aulast=Mouquinho&rft.aufirst=Ana&rft.au=Saavedra%2C+Mara&rft.au=Maiau%2C+Alexandre&rft.au=Petrova%2C+Krasimira&rft.au=Barros%2C+M.+Teresa&rft.au=Figueirinhas%2C+J.+L.&rft.au=Sotomayor%2C+Jo%C3%A3o&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABiphenyl" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/show_pathway?sco00621+SCO6442">"<i>Biphenyl degradation - Streptomyces coelicolor</i>, at GenomeNet Database"</a>. <i>genome.jp</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=genome.jp&rft.atitle=Biphenyl+degradation+-+Streptomyces+coelicolor%2C+at+GenomeNet+Database&rft_id=http%3A%2F%2Fwww.genome.jp%2Fdbget-bin%2Fshow_pathway%3Fsco00621%2BSCO6442&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABiphenyl" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>"Isolation and Identification of Biphenyls from West Edmond Crude Oil". N. G. Adams and D. M. Richardson. <i>Analytical Chemistry</i> 1953 25 (7), 1073–1074.</li> <li><i>Biphenyl (1,1-Biphenyl)</i>. Wiley/VCH, Weinheim (1991), <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-28277-7" title="Special:BookSources/3-527-28277-7">3-527-28277-7</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Biphenyl&action=edit&section=10" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0106&p_version=2">International Chemical Safety Card 0106</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0239.html">CDC - NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060304144243/http://www.npi.gov.au/database/substance-info/profiles/14.html">National Pollutant Inventory - Biphenyl</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20111217024943/http://msds.chem.ox.ac.uk/BI/biphenyl.html">External MSDS</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 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href="/wiki/Cultivar" title="Cultivar">cultivars</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_macrophylla" title="Citrus macrophylla">Alemow</a></li> <li><a href="/wiki/Amanatsu" title="Amanatsu">Amanatsu</a></li> <li><a href="/wiki/Assam_lemon" title="Assam lemon">Assam lemon</a></li> <li><a href="/wiki/Bergamot_orange" title="Bergamot orange">Bergamot orange</a></li> <li><a href="/wiki/Bizzarria" title="Bizzarria">Bizzarria</a></li> <li><a href="/wiki/Bitter_orange" title="Bitter orange">Bitter orange</a></li> <li><a href="/wiki/Blood_lime" title="Blood lime">Blood lime</a></li> <li><a href="/wiki/Blood_orange" title="Blood orange">Blood orange</a></li> <li><a href="/wiki/Byeonggyul" title="Byeonggyul">Byeonggyul</a></li> <li><a href="/wiki/Biasong" class="mw-redirect" title="Biasong">Biasong</a></li> <li><a href="/wiki/Cam_s%C3%A0nh" title="Cam sành">Cam sành</a></li> <li><a href="/wiki/Cara_cara_navel" title="Cara cara navel">Cara cara navel</a></li> <li><a href="/wiki/Citrange" title="Citrange">Citrange</a></li> <li><a href="/wiki/Citrumelo" title="Citrumelo">Citrumelo</a></li> <li><a href="/wiki/Clementine" title="Clementine">Clementine</a></li> <li><a href="/wiki/Coorg_orange" title="Coorg orange">Coorg orange</a></li> <li><a href="/wiki/Daidai" title="Daidai">Daidai</a></li> <li><a href="/wiki/Dekopon" title="Dekopon">Dekopon</a></li> <li><a href="/wiki/%27Encore%27_mandarin" title="'Encore' mandarin">Encore</a></li> <li><a href="/wiki/Fairchild_tangerine" title="Fairchild tangerine">Fairchild tangerine</a></li> <li><a href="/wiki/Florentine_citron" title="Florentine citron">Florentine citron</a></li> <li><a href="/wiki/Forbidden_fruit_(citrus)" title="Forbidden fruit (citrus)">Forbidden fruit</a></li> <li><a href="/wiki/Citrus_assamensis" title="Citrus assamensis">Ginger lime</a></li> <li><a href="/wiki/Haruka_(citrus)" title="Haruka (citrus)">Haruka</a></li> <li><a href="/wiki/Hassaku" title="Hassaku">Hassaku</a></li> <li><a href="/wiki/Hebesu" title="Hebesu">Hebesu</a></li> <li><a href="/wiki/Heen_naran" title="Heen naran">Heen naran</a></li> <li><a href="/wiki/Hyuganatsu" title="Hyuganatsu">Hyuganatsu</a></li> <li><a href="/wiki/Imperial_lemon" title="Imperial lemon">Imperial lemon</a></li> <li><a href="/wiki/Citrus_indica" title="Citrus indica">Indian wild orange</a></li> <li><a href="/wiki/Iyokan" title="Iyokan">Iyokan</a></li> <li><a href="/wiki/Jabara_(citrus)" title="Jabara (citrus)">Jabara</a></li> <li><a href="/wiki/Jaffa_orange" title="Jaffa orange">Jaffa orange</a></li> <li><a href="/wiki/Jamaican_tangelo" title="Jamaican tangelo">Jamaican tangelo</a></li> <li><a href="/wiki/Kabbad" title="Kabbad">Kabbad</a></li> <li><a href="/wiki/Kabosu" title="Kabosu">Kabosu</a></li> <li><a href="/wiki/Kaji_Nemu" title="Kaji Nemu">Kaji Nemu</a></li> <li><a href="/wiki/Citrus_gracilis" title="Citrus gracilis">Kakadu lime</a></li> <li><a href="/wiki/Kalpi_(fruit)" title="Kalpi (fruit)">Kalpi</a></li> <li><a href="/wiki/Kanpei" title="Kanpei">Kanpei</a></li> <li><a href="/wiki/Kawachi_bankan" title="Kawachi bankan">Kawachi bankan</a></li> <li><a href="/wiki/Key_lime" title="Key lime">Key lime</a></li> <li><a href="/wiki/Citrus_latipes" title="Citrus latipes">Khasi papeda</a></li> <li><a href="/wiki/Kinkoji_unshiu" title="Kinkoji unshiu">Kinkoji unshiu</a></li> <li><a href="/wiki/Kinnow" title="Kinnow">Kinnow</a></li> <li><a href="/wiki/Kishu_mikan" title="Kishu mikan">Kishu mikan</a></li> <li><a href="/wiki/Kiyomi" title="Kiyomi">Kiyomi</a></li> <li><a href="/wiki/Kobayashi_mikan" title="Kobayashi mikan">Kobayashi mikan</a></li> <li><a href="/wiki/Koji_orange" title="Koji orange">Koji</a></li> <li><a href="/wiki/Komikan_(fruit)" title="Komikan (fruit)">Komikan</a></li> <li><a href="/wiki/Laraha" title="Laraha">Laraha</a></li> <li><a href="/wiki/Lemonade_fruit" title="Lemonade fruit">Lemonade fruit</a></li> <li><a href="/wiki/Lim%C3%B3n_de_Pica" title="Limón de Pica">Limón de Pica</a></li> <li><a href="/wiki/Lumia_(citrus)" title="Lumia (citrus)">Lumia</a></li> <li><a href="/wiki/Mandelo" title="Mandelo">Mandelo</a></li> <li><a href="/wiki/Mandora_(fruit)" title="Mandora (fruit)">Mandora</a></li> <li><a href="/wiki/Citrus_macroptera" title="Citrus macroptera">Melanesian papeda</a></li> <li><a href="/wiki/Melogold" title="Melogold">Melogold</a></li> <li><a href="/wiki/Meyer_lemon" title="Meyer lemon">Meyer lemon</a></li> <li><a href="/wiki/Micrantha_(citrus)" title="Micrantha (citrus)">Micrantha</a></li> <li><a href="/wiki/Midknight_Valencia_Orange" title="Midknight Valencia Orange">Midknight Valencia Orange</a></li> <li><a href="/wiki/Murcott_(fruit)" title="Murcott (fruit)">Murcott</a></li> <li><a href="/wiki/Citrus_myrtifolia" title="Citrus myrtifolia">Myrtle-leaved orange tree</a></li> <li><a href="/wiki/Nagpur_orange" title="Nagpur orange">Nagpur orange</a></li> <li><a href="/wiki/Citrus_%C3%97_amblycarpa" title="Citrus × amblycarpa">Nasnaran</a></li> <li><a href="/wiki/New_Zealand_grapefruit" title="New Zealand grapefruit">New Zealand grapefruit</a></li> <li><a href="/wiki/%C5%8Cgonkan" title="Ōgonkan">Ōgonkan</a></li> <li><a href="/wiki/Orangelo" title="Orangelo">Orangelo/Chironja</a></li> <li><a href="/wiki/Oroblanco" title="Oroblanco">Oroblanco</a></li> <li><a href="/wiki/Palestinian_sweet_lime" title="Palestinian sweet lime">Palestinian sweet lime</a></li> <li><a href="/wiki/Persian_lime" title="Persian lime">Persian lime</a></li> <li><a href="/wiki/Pixie_mandarin" title="Pixie mandarin">Pixie mandarin</a></li> <li><a href="/wiki/Pompia" title="Pompia">Pompia</a></li> <li><a href="/wiki/Ponderosa_lemon" title="Ponderosa lemon">Ponderosa lemon</a></li> <li><a href="/wiki/Ponkan" title="Ponkan">Ponkan</a></li> <li><a href="/wiki/Rangpur_(fruit)" title="Rangpur (fruit)">Rangpur</a></li> <li><a href="/wiki/Reikou" title="Reikou">Reikou</a></li> <li><a href="/wiki/Rhobs_el_Arsa" title="Rhobs el Arsa">Rhobs el Arsa</a></li> <li><a href="/wiki/Rough_lemon" title="Rough lemon">Rough lemon</a></li> <li><a href="/wiki/Samuyao" class="mw-redirect" title="Samuyao">Samuyao</a></li> <li><a href="/wiki/Sanbokan" title="Sanbokan">Sanbokan</a></li> <li><a href="/wiki/Citrus_unshiu" title="Citrus unshiu">Satsuma mandarin</a></li> <li><a href="/wiki/Setoka" title="Setoka">Setoka</a></li> <li><a href="/wiki/Shangjuan" title="Shangjuan">Shangjuan</a></li> <li><a href="/wiki/Shonan_Gold" title="Shonan Gold">Shonan Gold</a></li> <li><a href="/wiki/Smith_Red_Valencia" title="Smith Red Valencia">Smith Red Valencia</a></li> <li><a href="/wiki/Sudachi" title="Sudachi">Sudachi</a></li> <li><a href="/wiki/Koji_orange#Varieties" title="Koji orange">Suruga yuko</a></li> <li><a href="/wiki/Sweet_lemon" title="Sweet lemon">Sweet lemon</a></li> <li><a href="/wiki/Citrus_limetta" title="Citrus limetta">Sweet limetta</a></li> <li><a href="/wiki/Tangelo" title="Tangelo">Tangelo</a></li> <li><a href="/wiki/Tangerine" title="Tangerine">Tangerine</a></li> <li><a href="/wiki/Tangor" title="Tangor">Tangor</a></li> <li><a href="/wiki/Tsunonozomi" title="Tsunonozomi">Tsunonozomi</a></li> <li><a href="/wiki/Valencia_orange" title="Valencia orange">Valencia orange</a></li> <li><a href="/wiki/Variegated_pink_lemon" title="Variegated pink lemon">Variegated pink lemon</a></li> <li><a href="/wiki/Volkamer_lemon" title="Volkamer lemon">Volkamer lemon</a></li> <li><a href="/wiki/Citrus_longispina" title="Citrus longispina">Winged lime</a></li> <li><a href="/wiki/X%C3%A3_%C4%90o%C3%A0i_orange" title="Xã Đoài orange">Xã Đoài orange</a></li> <li><a href="/wiki/Y%C5%ABk%C5%8D" title="Yūkō">Yūkō</a></li> <li><a href="/wiki/Yuzu" title="Yuzu">Yuzu</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Citron" title="Citron">Citrons</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Balady_citron" title="Balady citron">Balady citron</a></li> <li><a href="/wiki/Corsican_citron" title="Corsican citron">Corsican citron</a></li> <li><a href="/wiki/Diamante_citron" title="Diamante citron">Diamante citron</a></li> <li><a href="/wiki/Fingered_citron" class="mw-redirect" title="Fingered citron">Fingered citron/Buddha's hand</a></li> <li><a href="/wiki/Greek_citron" title="Greek citron">Greek citron</a></li> <li><a href="/wiki/Moroccan_citron" title="Moroccan citron">Moroccan citron</a></li> <li><a href="/wiki/Yemenite_citron" title="Yemenite citron">Yemenite citron</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mandarin_orange_varieties" title="Mandarin orange varieties">Mandarin oranges</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_reshni" title="Citrus reshni">Cleopatra mandarin</a></li> <li><a href="/wiki/Citrus_depressa" title="Citrus depressa">Shīkwāsā</a></li> <li><a href="/wiki/Nanfengmiju" title="Nanfengmiju">Nanfengmiju</a></li> <li><a href="/wiki/Tachibana_orange" title="Tachibana orange">Tachibana</a></li> <li><a href="/wiki/Citrus_x_deliciosa" class="mw-redirect" title="Citrus x deliciosa">Willowleaf orange</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Papeda_(citrus)" title="Papeda (citrus)">Papedas</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_celebica" class="mw-redirect" title="Citrus celebica">Celebes papeda</a></li> <li><a href="/wiki/Citrus_halimii" title="Citrus halimii">Mountain "citron"</a></li> <li><a href="/wiki/Citrus_ichangensis" class="mw-redirect" title="Citrus ichangensis">Ichang papeda</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pomelos" class="mw-redirect" title="Pomelos">Pomelos</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Banpeiyu" title="Banpeiyu">Banpeiyu</a></li> <li><a href="/wiki/Dangyuja" title="Dangyuja">Dangyuja</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Kumquat" title="Kumquat">Kumquats</a> group</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Kumquat species</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_hindsii" title="Citrus hindsii">Hong Kong kumquat</a></li> <li><a href="/wiki/Citrus_crassifolia" title="Citrus crassifolia">Meiwa kumquat</a></li> <li><a href="/wiki/Citrus_margarita" title="Citrus margarita">Oval kumquat</a></li> <li><a href="/wiki/Citrus_japonica" title="Citrus japonica">Round kumquat</a></li> <li><a href="/wiki/Citrus_obovata" title="Citrus obovata">Jiangsu kumquat</a></li> <li><a href="/wiki/Citrus_swinglei" title="Citrus swinglei">Malayan kumquat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kumquat hybrids <br />(<a href="/wiki/Hybrid_name" title="Hybrid name">×</a> <a href="/wiki/Citrofortunella" title="Citrofortunella">Citrofortunella</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calamansi" title="Calamansi">Calamansi</a></li> <li><a href="/wiki/Citrangequat" title="Citrangequat">Citrangequat</a></li> <li><a href="/wiki/Limequat" title="Limequat">Limequat</a></li> <li><a href="/wiki/Mandarinquat" title="Mandarinquat">Mandarinquat</a></li> <li><a href="/wiki/Procimequat" title="Procimequat">Procimequat</a></li> <li><a href="/wiki/Sunquat" title="Sunquat">Sunquat</a></li> <li><a href="/wiki/Yuzuquat" title="Yuzuquat">Yuzuquat</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Australian_lime" title="Australian lime">Australian<br />and Papuan<br />wild limes group</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><i>Eromocitrus</i> <br /> <small>(former genera)</small></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_glauca" title="Citrus glauca">Desert lime</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Microcitrus</i> <br /> <small>(former genera)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_warburgiana" title="Citrus warburgiana">New Guinea wild lime</a></li> <li><a href="/wiki/Citrus_australis" title="Citrus australis">Australian round lime</a></li> <li><a href="/wiki/Citrus_inodora" title="Citrus inodora">Russell River lime</a></li> <li><a href="/wiki/Citrus_maideniana" class="mw-redirect" title="Citrus maideniana">Maiden's wild lime</a></li> <li><a href="/wiki/Citrus_garrawayi" title="Citrus garrawayi">Mount White lime</a></li> <li><a href="/wiki/Citrus_australasica" title="Citrus australasica">Australian finger lime</a></li> <li><a href="/wiki/Citrus_wintersii" title="Citrus wintersii">Brown River finger lime</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Clymenia_(plant)" title="Clymenia (plant)">Clymenia</a></i> <br /> <small>(former genera)</small></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Clymenia_platypoda&action=edit&redlink=1" class="new" title="Clymenia platypoda (page does not exist)">Clymenia platypoda</a></li> <li><a href="/w/index.php?title=Clymenia_polyandra&action=edit&redlink=1" class="new" title="Clymenia polyandra (page does not exist)">Clymenia polyandra</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/False_orange" title="False orange">Oxanthera</a></i> <br /> <small>(former genera)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_oxanthera" title="Citrus oxanthera">Orange-flowered oxanthera</a></li> <li><a href="/wiki/Citrus_neocaledonica" title="Citrus neocaledonica">Large-leaf oxanthera</a></li> <li><a href="/wiki/Citrus_undulata" title="Citrus undulata">Wavy-leaf oxanthera</a></li> <li><i><a href="/wiki/Oxanthera_brevipes" title="Oxanthera brevipes">Oxanthera brevipes</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Citrus_taxonomy#Trifoliate_orange" title="Citrus taxonomy">Related genera</a><br />(perhaps<br />properly <i>Citrus</i>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Trifoliate_orange" title="Trifoliate orange">Poncirus</a></i>/<a href="/wiki/Trifoliate_orange" title="Trifoliate orange">Trifoliate orange</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drinks</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calamansi_juice" class="mw-redirect" title="Calamansi juice">Calamansi juice</a></li> <li><a href="/wiki/Ch%C5%ABhai" title="Chūhai">Chūhai</a></li> <li><a href="/wiki/Cura%C3%A7ao_(liqueur)" title="Curaçao (liqueur)">Curaçao</a></li> <li><a href="/wiki/Dried_lime_tea" title="Dried lime tea">Dried lime tea (noomi basra)</a></li> <li><a href="/wiki/Grapefruit_juice" title="Grapefruit juice">Grapefruit juice</a></li> <li><a href="/wiki/Lemonade" title="Lemonade">Lemonade</a></li> <li><a href="/wiki/Limeade" title="Limeade">Limeade</a></li> <li><a href="/wiki/Orange_juice" title="Orange juice">Orange juice</a></li> <li><a href="/wiki/Yuja-hwachae" title="Yuja-hwachae">Yuja-hwachae</a></li> <li><a href="/wiki/Yuja_tea" title="Yuja tea">Yuja tea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calcium_citrate" title="Calcium citrate">Calcium citrate</a></li> <li><a href="/wiki/Citric_acid" title="Citric acid">Citric acid</a></li> <li><a class="mw-selflink selflink">Lemonene</a></li> <li><a href="/wiki/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Neroli" title="Neroli">Neroli</a></li> <li><a href="/wiki/Orange_flower_water" title="Orange flower water">Orange flower water</a></li> <li><a href="/wiki/Orange_oil" title="Orange oil">Orange oil</a></li> <li><a href="/wiki/Orangeat" class="mw-redirect" title="Orangeat">Orangeat</a></li> <li><a href="/wiki/Succade" title="Succade">Succade</a></li> <li><a href="/wiki/Zest_(ingredient)" title="Zest (ingredient)">Zest</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_citrus_diseases" title="List of citrus diseases">Diseases</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrus_black_spot" title="Citrus black spot">Black spot</a></li> <li><a href="/wiki/Citrus_canker" title="Citrus canker">Canker</a></li> <li><a href="/wiki/Citrus_tristeza_virus" title="Citrus tristeza virus">CTV/Tristeza</a></li> <li><a href="/wiki/Citrus_exocortis" title="Citrus exocortis">Exocortis</a></li> <li><a href="/wiki/Citrus_greening_disease" title="Citrus greening disease">Greening</a></li> <li><a href="/wiki/Phoma_tracheiphila" title="Phoma tracheiphila">Mal secco</a></li> <li><a href="/wiki/Phytophthora" title="Phytophthora">Phytophthora</a> <ul><li><a href="/wiki/Phytophthora_citricola" title="Phytophthora citricola">citricola</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Citrus botanists</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clara_H._Hasse" title="Clara H. Hasse">Clara H. Hasse</a></li> <li><a href="/wiki/Robert_Willard_Hodgson" title="Robert Willard Hodgson">Robert Willard Hodgson</a></li> <li><a href="/wiki/Lena_B._Smithers_Hughes" title="Lena B. Smithers Hughes">Lena B. Smithers Hughes</a></li> <li><a href="/wiki/David_Mabberley" title="David Mabberley">David Mabberley</a></li> <li><a href="/wiki/Cl%C3%A9ment_Rodier" title="Clément Rodier">Clément Rodier</a></li> <li><a href="/wiki/Robert_Soost" title="Robert Soost">Robert Soost</a></li> <li><a href="/wiki/Walter_Tennyson_Swingle" title="Walter Tennyson Swingle">Walter Tennyson Swingle</a></li> <li><a href="/wiki/Ch%C5%8Dzabur%C5%8D_Tanaka" title="Chōzaburō Tanaka">Chōzaburō Tanaka</a></li> <li><a href="/wiki/Ikuro_Takahashi_(botanist)" title="Ikuro Takahashi (botanist)">Ikuro Takahashi</a></li> <li><a href="/wiki/Johann_Christoph_Volkamer" title="Johann Christoph Volkamer">Johann Christoph Volkamer</a></li> <li><a href="/wiki/Herbert_John_Webber" title="Herbert John Webber">Herbert John Webber</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/The_Citrus_Industry" title="The Citrus Industry">The Citrus Industry</a></i></li> <li><a href="/wiki/Citrus_production" title="Citrus production">Citrus production</a></li> <li><a href="/wiki/Citrus_rootstock" title="Citrus rootstock">Citrus rootstock</a></li> <li><a href="/wiki/Citrus_taxonomy" title="Citrus taxonomy">Citrus taxonomy</a></li> <li><a href="/wiki/Cold-hardy_citrus" title="Cold-hardy citrus">Cold-hardy citrus</a></li> <li><a href="/wiki/Hesperidium" title="Hesperidium">Hesperidium</a></li> <li><a href="/wiki/Japanese_citrus" title="Japanese citrus">Japanese citrus</a></li> <li><a href="/wiki/List_of_citrus_fruits" title="List of citrus fruits">List of citrus fruits</a></li> <li><a href="/wiki/Mother_Orange_Tree" title="Mother Orange Tree">Mother Orange Tree</a></li> <li><a href="/wiki/Orangery" title="Orangery">Orangery</a></li> <li><a href="/wiki/University_of_California_Citrus_Experiment_Station" title="University of California Citrus Experiment Station">University of California Citrus Experiment Station</a></li> <li><a href="/wiki/University_of_California,_Riverside_Citrus_Variety_Collection" title="University of California, Riverside Citrus Variety Collection">University of California, Riverside Citrus Variety Collection</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Citrus" title="Category:Citrus">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Citrus_production" title="Category:Citrus production">Production</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Citrus" class="extiw" title="commons:Category:Citrus">Commons</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Aryl_hydrocarbon_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Aryl_hydrocarbon_receptor_modulators" title="Template:Aryl hydrocarbon receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aryl_hydrocarbon_receptor_modulators" title="Template talk:Aryl hydrocarbon receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aryl_hydrocarbon_receptor_modulators" title="Special:EditPage/Template:Aryl hydrocarbon receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aryl_hydrocarbon_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">Aryl hydrocarbon receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor"><abbr title="Aryl hydrocarbon receptor">AhR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Aryl hydrocarbon receptor</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><i>Agonists:</i> <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> (e.g., <a href="/wiki/Lipoxin_A4" class="mw-redirect" title="Lipoxin A4">lipoxin A4</a>, <a href="/wiki/Prostaglandin_G2" title="Prostaglandin G2">prostaglandin G2</a>)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Dietary carotenoids</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Halogen" title="Halogen">Halogenated</a> <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a> (e.g., <a href="/wiki/Polychlorinated_dibenzodioxin" class="mw-redirect" title="Polychlorinated dibenzodioxin">polychlorinated dibenzodioxins</a> (e.g., <a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">TCDD</a>), <a href="/wiki/Dibenzofuran" title="Dibenzofuran">dibenzofurans</a>, <a class="mw-selflink selflink">biphenyls</a>)</li> <li><a href="/w/index.php?title=2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic_acid_methyl_ester&action=edit&redlink=1" class="new" title="2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic acid methyl ester (page does not exist)">ΙΤΕ</a></li> <li><a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">Modified low-density lipoproteins</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a> (e.g., <a href="/wiki/3-methylcholanthrene" class="mw-redirect" title="3-methylcholanthrene">3-methylcholanthrene</a>, <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo[a]pyrene</a>, <a href="/wiki/Benzanthracene" class="mw-redirect" title="Benzanthracene">benzanthracenes</a>, <a href="/wiki/Benzoflavone" class="mw-redirect" title="Benzoflavone">benzoflavones</a> (e.g., <a href="/wiki/%CE%92-naphthoflavone" class="mw-redirect" title="Β-naphthoflavone">β-naphthoflavone</a>))</li> <li><a href="/wiki/Tapinarof" title="Tapinarof">Tapinarof (benvitimod)</a></li> <li><a href="/wiki/Tetrapyrole" class="mw-redirect" title="Tetrapyrole">Tetrapyroles</a> (e.g., <a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a>)</li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> (e.g., <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>, <a href="/wiki/Indirubin" title="Indirubin">indirubin</a>)</li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=7-Ketocholesterol&action=edit&redlink=1" class="new" title="7-Ketocholesterol (page does not exist)">7-Ketocholesterol</a></li> <li><a href="/w/index.php?title=CH-223191&action=edit&redlink=1" class="new" title="CH-223191 (page does not exist)">CH-223191</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <div 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