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Available in 27 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-27" 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">27 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%A2%D8%B2%D9%88%D9%84%D9%8A%D9%86" title="آزولين – Arabic" lang="ar" hreflang="ar" data-title="آزولين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Azul%C3%A8" title="Azulè – Catalan" lang="ca" hreflang="ca" data-title="Azulè" 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/Azulen" title="Azulen – Czech" lang="cs" hreflang="cs" data-title="Azulen" 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/Azulen" title="Azulen – German" lang="de" hreflang="de" data-title="Azulen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%B6%CE%BF%CF%85%CE%BB%CE%AD%CE%BD%CE%B9%CE%BF" title="Αζουλένιο – Greek" lang="el" hreflang="el" data-title="Αζουλένιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Azuleno" title="Azuleno – Spanish" lang="es" hreflang="es" data-title="Azuleno" 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/Azuleno" title="Azuleno – Basque" lang="eu" hreflang="eu" data-title="Azuleno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D8%B2%D9%88%D9%84%D9%86" title="آزولن – Persian" lang="fa" hreflang="fa" data-title="آزولن" 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/Azul%C3%A8ne" title="Azulène – French" lang="fr" hreflang="fr" data-title="Azulène" 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/%EC%95%84%EC%A4%84%EB%A0%8C" title="아줄렌 – Korean" lang="ko" hreflang="ko" data-title="아줄렌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Azulene" title="Azulene – Italian" lang="it" hreflang="it" data-title="Azulene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Azul%C3%A9n" title="Azulén – Hungarian" lang="hu" hreflang="hu" data-title="Azulén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%B7%D1%83%D0%BB%D0%B5%D0%BD" title="Азулен – Macedonian" lang="mk" hreflang="mk" data-title="Азулен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Azuleen" title="Azuleen – Dutch" lang="nl" hreflang="nl" data-title="Azuleen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%BA%E3%83%AC%E3%83%B3" title="アズレン – Japanese" lang="ja" hreflang="ja" data-title="アズレン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Azulenlar" title="Azulenlar – Uzbek" lang="uz" hreflang="uz" data-title="Azulenlar" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Azuleno" title="Azuleno – Portuguese" lang="pt" hreflang="pt" data-title="Azuleno" 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/Azulen%C4%83" title="Azulenă – Romanian" lang="ro" hreflang="ro" data-title="Azulenă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%B7%D1%83%D0%BB%D0%B5%D0%BD" title="Азулен – Russian" lang="ru" hreflang="ru" data-title="Азулен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Azulen" title="Azulen – Serbian" lang="sr" hreflang="sr" data-title="Azulen" 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/Azulen" title="Azulen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Azulen" 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/Atsuleeni" title="Atsuleeni – Finnish" lang="fi" hreflang="fi" data-title="Atsuleeni" 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/Azulen" title="Azulen – Swedish" lang="sv" hreflang="sv" data-title="Azulen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AD%E0%B8%B0%E0%B8%8B%E0%B8%B9%E0%B8%A5%E0%B8%B5%E0%B8%99" title="อะซูลีน – Thai" lang="th" hreflang="th" data-title="อะซูลีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Azulen" title="Azulen – Turkish" lang="tr" hreflang="tr" data-title="Azulen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%B7%D1%83%D0%BB%D0%B5%D0%BD" title="Азулен – Ukrainian" lang="uk" hreflang="uk" data-title="Азулен" 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%96%81" title="薁 – Chinese" lang="zh" hreflang="zh" data-title="薁" 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/Q144362#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" 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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"><p class="mw-empty-elt"> </p> <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>Azulene </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Azulen_num.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Azulen_num.svg/120px-Azulen_num.svg.png" decoding="async" width="120" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Azulen_num.svg/180px-Azulen_num.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Azulen_num.svg/240px-Azulen_num.svg.png 2x" data-file-width="184" data-file-height="135" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Azulene_3d_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Azulene_3d_structure.png/120px-Azulene_3d_structure.png" decoding="async" width="120" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Azulene_3d_structure.png/180px-Azulene_3d_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Azulene_3d_structure.png/240px-Azulene_3d_structure.png 2x" data-file-width="982" data-file-height="740" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </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;">Azulene<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Bicyclo[5.3.0]decapentaene</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><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=275-51-4">275-51-4</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=c1cccc2cccc2c1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=31249">CHEBI:31249</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.8876.html">8876</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/100.005.449">100.005.449</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q144362#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C13392">C13392</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/9231">9231</a></span></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/82R6M9MGLP">82R6M9MGLP</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID2059770">DTXSID2059770</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q144362#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/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H<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: CUFNKYGDVFVPHO-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/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: CUFNKYGDVFVPHO-UHFFFAOYAT</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%;">c1cccc2cccc2c1</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>10</sub><span title="Hydrogen">H</span><sub>8</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="7002128174000000000♠"></span>128.174</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>99 to 100 °C (210 to 212 °F; 372 to 373 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>242 °C (468 °F; 515 K) </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>-98.5·10<sup>−6</sup> cm<sup>3</sup>/mol <p>g/L<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−1266.5 kcal/mol<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:#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> <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>Azulene</b> is an aromatic <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> and an <a href="/wiki/Valence_isomer" title="Valence isomer">isomer</a> of <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>. Naphthalene is colourless, whereas azulene is dark blue. The compound is named after its colour, as "azul" is <a href="/wiki/Spanish_language" title="Spanish language">Spanish</a> for blue. Two terpenoids, <a href="/wiki/Vetivazulene" title="Vetivazulene">vetivazulene</a> (4,8-dimethyl-2-isopropylazulene) and <a href="/wiki/Guaiazulene" title="Guaiazulene">guaiazulene</a> (1,4-dimethyl-7-isopropylazulene), that feature the azulene skeleton are found in nature as constituents of pigments in mushrooms, <a href="/wiki/Oil_of_guaiac" title="Oil of guaiac">guaiac wood oil</a>, and some marine invertebrates. </p><p>Azulene has a long history, dating back to the 15th century as the azure-blue <a href="/wiki/Chromophore" title="Chromophore">chromophore</a> obtained by <a href="/wiki/Steam_distillation" title="Steam distillation">steam distillation</a> of <a href="/wiki/Matricaria_recutita" class="mw-redirect" title="Matricaria recutita">German chamomile</a>. The chromophore was discovered in <a href="/wiki/Yarrow" class="mw-redirect" title="Yarrow">yarrow</a> and <a href="/wiki/Artemisia_(genus)" class="mw-redirect" title="Artemisia (genus)">wormwood</a> and named in 1863 by Septimus Piesse. Its structure was first reported by <a href="/wiki/Lavoslav_Ru%C5%BEi%C4%8Dka" class="mw-redirect" title="Lavoslav Ružička">Lavoslav Ružička</a>, followed by its <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> in 1937 by Placidus Plattner. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azulene&action=edit&section=1" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Lactarius_indigo_48568_edit.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Lactarius_indigo_48568_edit.jpg/220px-Lactarius_indigo_48568_edit.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Lactarius_indigo_48568_edit.jpg/330px-Lactarius_indigo_48568_edit.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Lactarius_indigo_48568_edit.jpg/440px-Lactarius_indigo_48568_edit.jpg 2x" data-file-width="3264" data-file-height="2448" /></a><figcaption>The blue color of the mushroom <i><a href="/wiki/Lactarius_indigo" title="Lactarius indigo">Lactarius indigo</a></i> is due to the azulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate.<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></figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Entoloma_hochstetteri.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Entoloma_hochstetteri.jpg/220px-Entoloma_hochstetteri.jpg" decoding="async" width="220" height="320" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Entoloma_hochstetteri.jpg/330px-Entoloma_hochstetteri.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Entoloma_hochstetteri.jpg/440px-Entoloma_hochstetteri.jpg 2x" data-file-width="633" data-file-height="920" /></a><figcaption>The blue color of the mushroom <i><a href="/wiki/Entoloma_hochstetteri" title="Entoloma hochstetteri">Entoloma hochstetteri</a></i> is also identified as another kind of azulene derivative: 7-acetyl-1,4-dimethylazulene.<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></figcaption></figure> <p>Azulene is usually viewed as resulting from fusion of <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> and <a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">cycloheptatriene</a> rings. Like naphthalene and <a href="/wiki/Cyclodecapentaene" title="Cyclodecapentaene">cyclodecapentaene</a>, it is a 10 <a href="/wiki/Pi_electron" class="mw-redirect" title="Pi electron">pi electron</a> system. It exhibits <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> properties: (i) the <a href="https://en.wiktionary.org/wiki/periphery" class="extiw" title="wikt:periphery">peripheral</a> bonds have similar lengths and (ii) it undergoes <a href="/wiki/Friedel-Crafts_reaction" class="mw-redirect" title="Friedel-Crafts reaction">Friedel-Crafts</a>-like substitutions. The stability gain from aromaticity is estimated to be half that of naphthalene. </p><p>Its <a href="/wiki/Molecular_dipole_moment" class="mw-redirect" title="Molecular dipole moment">dipole moment</a> is <span class="nowrap"><span data-sort-value="7000108000000000000♠"></span>1.08 <a href="/wiki/Debye" title="Debye">D</a></span>,<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> in contrast with naphthalene, which has a dipole moment of zero. This polarity can be explained by regarding azulene as the fusion of a 6 <a href="/wiki/Pi_bond" title="Pi bond">π-electron</a> <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl anion</a> and a 6 π-electron <a href="/wiki/Tropylium_cation" title="Tropylium cation">tropylium cation</a>: one electron from the seven-membered ring is transferred to the five-membered ring to give each ring aromatic stability by <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a>. Reactivity studies confirm that seven-membered ring is electrophilic and the five-membered ring is <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Azulene_resonance.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Azulene_resonance.png/350px-Azulene_resonance.png" decoding="async" width="350" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Azulene_resonance.png/525px-Azulene_resonance.png 1.5x, //upload.wikimedia.org/wikipedia/commons/9/94/Azulene_resonance.png 2x" data-file-width="669" data-file-height="156" /></a><figcaption></figcaption></figure> <p>The dipolar nature of the ground state is reflected in its deep colour, which is unusual for small unsaturated aromatic compounds.<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> Another notable feature of azulene is that it violates <a href="/wiki/Kasha%27s_rule" title="Kasha's rule">Kasha's rule</a> by exhibiting fluorescence from an upper-excited state (S<sub>2</sub> → S<sub>0</sub>).<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> </p> <div class="mw-heading mw-heading2"><h2 id="Organic_synthesis">Organic synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azulene&action=edit&section=2" title="Edit section: Organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synthetic routes to azulene have long been of interest because of its unusual structure.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 1939 the first method was reported by St. Pfau and Plattner <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> starting from <a href="/wiki/Indane" title="Indane">indane</a> and <a href="/wiki/Ethyl_diazoacetate" title="Ethyl diazoacetate">ethyl diazoacetate</a>. </p><p>An efficient <a href="/wiki/One-pot_synthesis" title="One-pot synthesis">one-pot</a> route entails <a href="/wiki/Annulation" title="Annulation">annulation</a> of <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> with unsaturated C<sub>5</sub>-<a href="/wiki/Synthon" title="Synthon">synthons</a>.<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> The alternative approach from <a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">cycloheptatriene</a> has long been known, one illustrative method being shown below.<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><sup id="cite_ref-Lemal_13-0" class="reference"><a href="#cite_note-Lemal-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Azulenesynthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Azulenesynthesis.png/720px-Azulenesynthesis.png" decoding="async" width="720" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Azulenesynthesis.png/1080px-Azulenesynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Azulenesynthesis.png/1440px-Azulenesynthesis.png 2x" data-file-width="2720" data-file-height="795" /></a><figcaption></figcaption></figure> <p>Procedure: </p> <ol><li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">cycloheptatriene</a> 2+2 <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> with dichloro <a href="/wiki/Ketene" title="Ketene">ketene</a></li> <li><a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> <a href="/wiki/Insertion_reaction" title="Insertion reaction">insertion reaction</a></li> <li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> reaction with <a href="/wiki/Dimethylformamide" title="Dimethylformamide">DMF</a></li> <li><a href="/wiki/Luche_reduction" title="Luche reduction">Luche reduction</a> to alcohol with <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination reaction</a> with <a href="/wiki/Burgess_reagent" title="Burgess reagent">Burgess reagent</a></li> <li><a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">oxidation</a> with <a href="/wiki/P-chloranil" class="mw-redirect" title="P-chloranil">p-chloranil</a></li> <li><a href="/wiki/Dehalogenation" title="Dehalogenation">dehalogenation</a> with <a href="/wiki/Polymethylhydrosiloxane" title="Polymethylhydrosiloxane">polymethylhydrosiloxane</a>, <a href="/wiki/Palladium(II)_acetate" title="Palladium(II) acetate">palladium(II) acetate</a>, potassium <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> and the <a href="/wiki/DPDB_ligand" class="mw-redirect" title="DPDB ligand">DPDB ligand</a></li></ol> <p>Another synthesis route starts from the of <a href="/wiki/Pyridinium" title="Pyridinium">pyridinium</a> or <a href="/wiki/Pyrylium" title="Pyrylium">pyrylium</a> salts with <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl anion</a>:<sup id="cite_ref-:0_14-0" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Azulene_synthesis_1.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Azulene_synthesis_1.png/220px-Azulene_synthesis_1.png" decoding="async" width="220" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/Azulene_synthesis_1.png/330px-Azulene_synthesis_1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/52/Azulene_synthesis_1.png/440px-Azulene_synthesis_1.png 2x" data-file-width="1840" data-file-height="601" /></a><figcaption></figcaption></figure> <p>Azulene can also be synthesized via a <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels Alder</a> and <a href="/wiki/Retro-Diels%E2%80%93Alder_reaction" title="Retro-Diels–Alder reaction">retro-Diels Alder reaction</a>:<sup id="cite_ref-:0_14-1" class="reference"><a href="#cite_note-:0-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Azulene_synthesis_2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Azulene_synthesis_2.png/220px-Azulene_synthesis_2.png" decoding="async" width="220" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Azulene_synthesis_2.png/330px-Azulene_synthesis_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/Azulene_synthesis_2.png/440px-Azulene_synthesis_2.png 2x" data-file-width="1268" data-file-height="922" /></a><figcaption></figcaption></figure> <p>The starting material of the above reaction can be generated through the <a href="/wiki/Flash_vacuum_pyrolysis" title="Flash vacuum pyrolysis">Flash Vacuum Pyrolysis</a> of phenyl propiolate. </p> <div class="mw-heading mw-heading2"><h2 id="Organometallic_complexes">Organometallic complexes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azulene&action=edit&section=3" title="Edit section: Organometallic complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, azulene serves as a ligand for low-valent metal centers. Illustrative complexes are (azulene)Mo<sub>2</sub>(CO)<sub>6</sub> and (azulene)Fe<sub>2</sub>(CO)<sub>5</sub>.<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="Derivatives">Derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azulene&action=edit&section=4" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1-Hydroxyazulene is an unstable green oil and it does not show <a href="/wiki/Keto%E2%80%93enol_tautomerism" class="mw-redirect" title="Keto–enol tautomerism">keto–enol tautomerism</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> 2-Hydroxyazulene is obtained by hydrolysis of 2-methoxyazulene with hydrobromic acid. It is stable and does show keto–enol tautomerism.<sup id="cite_ref-2-_and_6-_hydroxyazulene_17-0" class="reference"><a href="#cite_note-2-_and_6-_hydroxyazulene-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/PKa" class="mw-redirect" title="PKa">p<i>K</i><sub>a</sub></a> of 2-hydroxyazulene in water is 8.71. It is more acidic than <a href="/wiki/Phenol" title="Phenol">phenol</a> or <a href="/wiki/Naphthol" title="Naphthol">naphthol</a>. The p<i>K</i><sub>a</sub> of 6-hydroxyazulenes in water is 7.38 making it also more acidic than phenol or naphthol.<sup id="cite_ref-2-_and_6-_hydroxyazulene_17-1" class="reference"><a href="#cite_note-2-_and_6-_hydroxyazulene-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>In naphth[<i>a</i>]azulene, a <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a> ring is condensed at the 1,2-positions of azulene. In one such system<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> deviation from planarity is found, similar to that of <a href="/wiki/Helicene" title="Helicene">tetrahelicene</a>. </p><p><a href="/wiki/Guaiazulene" title="Guaiazulene">Guaiazulene</a> (1,4-dimethyl-7-isopropylazulene) is an alkylated derivative of azulene with an almost identical intensely blue colour. It is commercially available to the cosmetics industry where it functions as a skin conditioning agent. </p> <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=Azulene&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry2014" class="citation book cs1"><a 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"1-Hydroxyazulene and 3-hydroxyguaiazulene: Synthesis and their properties". <i><a href="/wiki/Tetrahedron_Letters" title="Tetrahedron Letters">Tetrahedron Letters</a></i>. <b>30</b> (48): 6693–6696. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2800%2970653-8">10.1016/S0040-4039(00)70653-8</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=1-Hydroxyazulene+and+3-hydroxyguaiazulene%3A+Synthesis+and+their+properties&rft.volume=30&rft.issue=48&rft.pages=6693-6696&rft.date=1989&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2800%2970653-8&rft.aulast=Asao&rft.aufirst=Toyonobu&rft.au=Shunji+Ito&rft.au=Noboru+Morita&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAzulene" class="Z3988"></span></span> </li> <li id="cite_note-2-_and_6-_hydroxyazulene-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-2-_and_6-_hydroxyazulene_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-2-_and_6-_hydroxyazulene_17-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakaseToyonobu_AsaoYoshikazu_TakagiTetsuo_Nozoe1968" class="citation journal cs1">Takase, Kahei; Toyonobu Asao; Yoshikazu Takagi; Tetsuo Nozoe (1968). "Syntheses and some properties of 2- and 6-hydroxyazulenes". <i><a href="/wiki/Chemical_Communications" class="mw-redirect" title="Chemical Communications">Chemical Communications</a></i> (7): 368b–370. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC1968000368B">10.1039/C1968000368B</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=Syntheses+and+some+properties+of+2-+and+6-hydroxyazulenes&rft.issue=7&rft.pages=368b-370&rft.date=1968&rft_id=info%3Adoi%2F10.1039%2FC1968000368B&rft.aulast=Takase&rft.aufirst=Kahei&rft.au=Toyonobu+Asao&rft.au=Yoshikazu+Takagi&rft.au=Tetsuo+Nozoe&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAzulene" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYamamuraKawabataKimuraEda2005" class="citation journal cs1">Yamamura, Kimiaki; Kawabata, Shizuka; Kimura, Takatomo; Eda, Kazuo; Hashimoto, Masao (2005). "Novel Synthesis of Benzalacetone Analogues of Naphth[<i>a</i>]azulenes by Intramolecular Tropylium Ion-Mediated Furan Ring-Opening Reaction and X-ray Investigation of a Naphth[1,2-<i>a</i>]azulene Derivative". <i><a href="/wiki/The_Journal_of_Organic_Chemistry" title="The Journal of Organic Chemistry">The Journal of Organic Chemistry</a></i>. <b>70</b> (22): 8902–6. <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%2Fjo051409f">10.1021/jo051409f</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/16238325">16238325</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Novel+Synthesis+of+Benzalacetone+Analogues+of+Naphth%5Ba%5Dazulenes+by+Intramolecular+Tropylium+Ion-Mediated+Furan+Ring-Opening+Reaction+and+X-ray+Investigation+of+a+Naphth%5B1%2C2-a%5Dazulene+Derivative&rft.volume=70&rft.issue=22&rft.pages=8902-6&rft.date=2005&rft_id=info%3Adoi%2F10.1021%2Fjo051409f&rft_id=info%3Apmid%2F16238325&rft.aulast=Yamamura&rft.aufirst=Kimiaki&rft.au=Kawabata%2C+Shizuka&rft.au=Kimura%2C+Takatomo&rft.au=Eda%2C+Kazuo&rft.au=Hashimoto%2C+Masao&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAzulene" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azulene&action=edit&section=6" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/MSDS" class="mw-redirect" title="MSDS">MSDS</a> <a rel="nofollow" class="external text" href="http://physchem.ox.ac.uk/MSDS/AZ/azulene.html">Website</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20071018223113/http://physchem.ox.ac.uk/MSDS/AZ/azulene.html">Archived</a> 18 October 2007 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a href="/wiki/MSDS" class="mw-redirect" title="MSDS">MSDS</a> <a rel="nofollow" class="external text" href="http://www.chemicalland21.com/lifescience/foco/AZULENE.htm">Website</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 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style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Polycyclic_aromatic_hydrocarbons" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align: center;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:PAHs" title="Template:PAHs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PAHs" title="Template talk:PAHs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PAHs" title="Special:EditPage/Template:PAHs"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polycyclic_aromatic_hydrocarbons" style="font-size:114%;margin:0 4em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">2 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a class="mw-selflink selflink">Azulene</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">3 rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acenaphthene" title="Acenaphthene">Acenaphthene</a></li> <li><a href="/wiki/Acenaphthylene" title="Acenaphthylene">Acenaphthylene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Phenalene" title="Phenalene">Phenalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">4 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benz(a)anthracene" title="Benz(a)anthracene">Benz[<i>a</i>]anthracene</a></li> <li><a href="/wiki/Benzo(a)fluorene" title="Benzo(a)fluorene">Benzo[<i>a</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">Benzo[<i>c</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)phenanthrene" title="Benzo(c)phenanthrene">Benzo[<i>c</i>]phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Fluoranthene" title="Fluoranthene">Fluoranthene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Triphenylene" title="Triphenylene">Triphenylene</a></li> <li><a href="/wiki/Tricyclobutabenzene" title="Tricyclobutabenzene">Tricyclobutabenzene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">5 rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benz(e)acephenanthrylene" title="Benz(e)acephenanthrylene">Benz[<i>e</i>]acephenanthrylene</a></li> <li><a href="/wiki/Benzopyrene" title="Benzopyrene">Benzopyrene</a> <ul><li><a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a></li> <li><a href="/wiki/Benzo(e)pyrene" title="Benzo(e)pyrene">Benzo[<i>e</i>]pyrene</a></li> <li><a href="/wiki/Olympicene" title="Olympicene">6<i>H</i>-Benzo[<i>cd</i>]pyrene(Olympicene)</a></li></ul></li> <li><a href="/wiki/Benzo(a)fluoranthene" title="Benzo(a)fluoranthene">Benzo[<i>a</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(b)fluoranthene" class="mw-redirect" title="Benzo(b)fluoranthene">Benzo[<i>b</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(j)fluoranthene" title="Benzo(j)fluoranthene">Benzo[<i>j</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(k)fluoranthene" title="Benzo(k)fluoranthene">Benzo[<i>k</i>]fluoranthene</a></li> <li><a href="/wiki/Bicalicene" title="Bicalicene">trans-Bicalicene</a></li> <li><a href="/wiki/Dibenz(a,h)anthracene" title="Dibenz(a,h)anthracene">Dibenz[<i>a</i>,<i>h</i>]anthracene</a></li> <li><a href="/wiki/Dibenz(a,j)anthracene" title="Dibenz(a,j)anthracene">Dibenz[<i>a</i>,<i>j</i>]anthracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/w/index.php?title=Pentaphene&action=edit&redlink=1" class="new" title="Pentaphene (page does not exist)">Pentaphene</a></li> <li><a href="/wiki/Perylene" title="Perylene">Perylene</a></li> <li><a href="/wiki/Picene" title="Picene">Picene</a></li> <li><a href="/wiki/Tetraphenylene" title="Tetraphenylene">Tetraphenylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">6 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthanthrene" title="Anthanthrene">Anthanthrene</a></li> <li><a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">Benzo[<i>ghi</i>]perylene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">Dibenzopyrenes</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Triangulene" title="Triangulene">Triangulene</a></li> <li><a href="/wiki/Zethrene" title="Zethrene">Zethrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">7+ rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coronene" title="Coronene">Coronene</a></li> <li><a href="/wiki/Dicoronylene" title="Dicoronylene">Dicoronylene</a></li> <li><a href="/wiki/Diindenoperylene" title="Diindenoperylene">Diindenoperylene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li> <li><a href="/wiki/Hexabenzocoronene" title="Hexabenzocoronene">Hexabenzocoronene</a> (<a href="/wiki/Hexa-cata-hexabenzocoronene" title="Hexa-cata-hexabenzocoronene">Hexa-cata-</a>)</li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li> <li><a href="/wiki/Ovalene" title="Ovalene">Ovalene</a></li> <li><a href="/wiki/Rubicene" title="Rubicene">Rubicene</a></li> <li><a href="/wiki/Rubrene" title="Rubrene">Rubrene</a></li> <li><a href="/wiki/Sumanene" title="Sumanene">Sumanene</a></li> <li><a href="/wiki/Superphenalene" title="Superphenalene">Superphenalene</a></li> <li><a href="/wiki/Trinaphthylene" title="Trinaphthylene">Trinaphthylene</a></li> <li><a href="/wiki/Truxene" title="Truxene">Truxene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">General classes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acene" title="Acene">Acene</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulene</a></li> <li><a href="/wiki/Cyclacene" title="Cyclacene">Cyclacene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicene</a></li> <li><a href="/wiki/Phenacene" title="Phenacene">Phenacene</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a 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