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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Vinyl alcohol</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 32 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-32" 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">32 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/%D9%83%D8%AD%D9%88%D9%84_%D8%A7%D9%84%D9%81%D8%A7%D9%8A%D9%86%D9%8A%D9%84" title="كحول الفاينيل – Arabic" lang="ar" hreflang="ar" data-title="كحول الفاينيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%88%DB%8C%D9%86%DB%8C%D9%84_%D8%A7%D9%84%DA%A9%D9%88%D9%84" title="وینیل الکول – South Azerbaijani" lang="azb" hreflang="azb" data-title="وینیل الکول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Etenol" title="Etenol – Bosnian" lang="bs" hreflang="bs" data-title="Etenol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Etenol" title="Etenol – Catalan" lang="ca" hreflang="ca" data-title="Etenol" 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/Vinylalkohol" title="Vinylalkohol – Czech" lang="cs" hreflang="cs" data-title="Vinylalkohol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Vinylalkohol" title="Vinylalkohol – Danish" lang="da" hreflang="da" data-title="Vinylalkohol" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ethenol" title="Ethenol – German" lang="de" hreflang="de" data-title="Ethenol" 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%B9%CE%B8%CE%B5%CE%BD%CF%8C%CE%BB%CE%B7" title="Αιθενόλη – Greek" lang="el" hreflang="el" data-title="Αιθενόλη" 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/Etenol" title="Etenol – Spanish" lang="es" hreflang="es" data-title="Etenol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Vinila_alkoholo" title="Vinila alkoholo – Esperanto" lang="eo" hreflang="eo" data-title="Vinila alkoholo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Binil_alkohol" title="Binil alkohol – Basque" lang="eu" hreflang="eu" data-title="Binil alkohol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%DB%8C%D9%86%DB%8C%D9%84_%D8%A7%D9%84%DA%A9%D9%84" title="وینیل الکل – Persian" lang="fa" hreflang="fa" data-title="وینیل الکل" 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/%C3%89th%C3%A9nol" title="Éthénol – French" lang="fr" hreflang="fr" data-title="Éthénol" 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%B9%84%EB%8B%90_%EC%95%8C%EC%BD%94%EC%98%AC" title="비닐 알코올 – Korean" lang="ko" hreflang="ko" data-title="비닐 알코올" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Vinil_alkohol" title="Vinil alkohol – Indonesian" lang="id" hreflang="id" data-title="Vinil alkohol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Etenolo" title="Etenolo – Italian" lang="it" hreflang="it" data-title="Etenolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%95%D7%99%D7%A0%D7%99%D7%9C_%D7%90%D7%9C%D7%9B%D7%95%D7%94%D7%95%D7%9C" title="ויניל אלכוהול – Hebrew" lang="he" hreflang="he" data-title="ויניל אלכוהול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%92%D0%B8%D0%BD%D0%B8%D0%BB_%D1%81%D0%BF%D0%B8%D1%80%D1%82%D0%B8" title="Винил спирти – Kyrgyz" lang="ky" hreflang="ky" data-title="Винил спирти" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Etenol" title="Etenol – Hungarian" lang="hu" hreflang="hu" data-title="Etenol" 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/Vinylalcohol" title="Vinylalcohol – Dutch" lang="nl" hreflang="nl" data-title="Vinylalcohol" 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%8B%E3%83%AB%E3%82%A2%E3%83%AB%E3%82%B3%E3%83%BC%E3%83%AB" title="ビニルアルコール – Japanese" lang="ja" hreflang="ja" data-title="ビニルアルコール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkohol_winylowy" title="Alkohol winylowy – Polish" lang="pl" hreflang="pl" data-title="Alkohol winylowy" 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/Etenol" title="Etenol – Portuguese" lang="pt" hreflang="pt" data-title="Etenol" 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/Etenol" title="Etenol – Romanian" lang="ro" hreflang="ro" data-title="Etenol" 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%92%D0%B8%D0%BD%D0%B8%D0%BB%D0%BE%D0%B2%D1%8B%D0%B9_%D1%81%D0%BF%D0%B8%D1%80%D1%82" title="Виниловый спирт – Russian" lang="ru" hreflang="ru" data-title="Виниловый спирт" 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/Vinil_alkohol" title="Vinil alkohol – Serbian" lang="sr" hreflang="sr" data-title="Vinil alkohol" 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/Vinil_alkohol" title="Vinil alkohol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vinil alkohol" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Etenol" title="Etenol – Swedish" lang="sv" hreflang="sv" data-title="Etenol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B5%E0%AE%BF%E0%AE%A9%E0%AF%88%E0%AE%B2%E0%AF%8D_%E0%AE%86%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AE%95%E0%AE%BE%E0%AE%B2%E0%AF%8D" title="வினைல் ஆல்ககால் – Tamil" lang="ta" hreflang="ta" data-title="வினைல் ஆல்ககால்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Vinil_alkol" title="Vinil alkol – Turkish" lang="tr" hreflang="tr" data-title="Vinil alkol" 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%92%D1%96%D0%BD%D1%96%D0%BB%D0%BE%D0%B2%D0%B8%D0%B9_%D1%81%D0%BF%D0%B8%D1%80%D1%82" title="Вініловий спирт – Ukrainian" lang="uk" hreflang="uk" data-title="Вініловий спирт" 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/%E4%B9%99%E7%83%AF%E9%86%87" title="乙烯醇 – Chinese" lang="zh" hreflang="zh" data-title="乙烯醇" 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/Q409591#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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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">Not to be confused with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> or <a href="/wiki/Ethynol" title="Ethynol">ethynol</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Vinyl alcohol </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:Ethenol-2D.png" class="mw-file-description" title="Structural formula of ethenol"><img alt="Structural formula of ethenol" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Ethenol-2D.png/120px-Ethenol-2D.png" decoding="async" width="120" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Ethenol-2D.png/180px-Ethenol-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Ethenol-2D.png/240px-Ethenol-2D.png 2x" data-file-width="956" data-file-height="1100" /></a><figcaption>Structural formula of ethenol</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethenol-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of ethenol"><img alt="Ball-and-stick model of ethenol" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Ethenol-3D-balls.png/130px-Ethenol-3D-balls.png" decoding="async" width="130" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Ethenol-3D-balls.png/195px-Ethenol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Ethenol-3D-balls.png/260px-Ethenol-3D-balls.png 2x" data-file-width="1037" data-file-height="1100" /></a><figcaption>Ball-and-stick model of ethenol</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Ethenol</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;">Hydroxyethene<br />Hydroxyethylene<br />Ethylenol</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=557-75-5">557-75-5</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=OC%3DC">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL76101">ChEMBL76101</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.10726.html">10726</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/100.008.350">100.008.350</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409591#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><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/11199">11199</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/GO1N1ZPR3B">GO1N1ZPR3B</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/DTXSID8051467">DTXSID8051467</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409591#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C2H4O/c1-2-3/h2-3H,1H2<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: IMROMDMJAWUWLK-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=1S/C2H4O/c1-2-3/h2-3H,1H2</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=1S/C2H4O/c1-2-3/h2-3H,1H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IMROMDMJAWUWLK-UHFFFAOYSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">OC=C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>2</sub>H<sub>4</sub>O  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>44.053 g/mol    </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=470630576&page2=Vinyl+alcohol">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>Vinyl alcohol</b>, also called <b>ethenol</b> (IUPAC name; not ethanol) or <b>ethylenol</b>, is the simplest <a href="/wiki/Enol" title="Enol">enol</a>. With the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">2</sub>CH<a href="/wiki/Oxygen" title="Oxygen">O</a>H</span>, it is a labile compound that converts to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> immediately upon isolation near room temperature.<sup id="cite_ref-March_1-0" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is not a practical precursor to any compound. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinyl_alcohol&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vinyl alcohol can be formed by the pyrolytic <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination</a> of water from <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a> at a temperature of 900 °C and low pressure. Such processes are of no practical importance.<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> <div class="mw-heading mw-heading2"><h2 id="Tautomerization_of_vinyl_alcohol_to_acetaldehyde">Tautomerization of vinyl alcohol to acetaldehyde</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinyl_alcohol&action=edit&section=2" title="Edit section: Tautomerization of vinyl alcohol to acetaldehyde"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Under normal conditions, vinyl alcohol converts (<a href="/wiki/Tautomer" title="Tautomer">tautomerizes</a>) to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg/250px-Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg.png" decoding="async" width="250" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg/375px-Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg/500px-Ethenol%E2%80%93ethanal_tautom%C3%A9risation.svg.png 2x" data-file-width="393" data-file-height="146" /></a></span><div style="clear:left;" class=""></div></dd></dl> <p>At room temperature, acetaldehyde (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>CC(O)H</span>) is more stable than vinyl alcohol (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=CHOH</span>) by 42.7 kJ/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> Vinyl alcohol gas isomerizes to the aldehyde with a half-life of 30 min at room temperature.<sup id="cite_ref-March_1-1" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=CHOH → H<sub class="template-chem2-sub">3</sub>CC(O)H</span></dd></dl> <figure typeof="mw:File/Thumb"><a href="/wiki/File:WackerCycleKeith%26HenryImp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/WackerCycleKeith%26HenryImp.png/250px-WackerCycleKeith%26HenryImp.png" decoding="async" width="232" height="205" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/WackerCycleKeith%26HenryImp.png/500px-WackerCycleKeith%26HenryImp.png 1.5x" data-file-width="1157" data-file-height="1024" /></a><figcaption>The industrial synthesis of <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> (<a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a>) proceeds via the intermediacy of a vinyl alcohol complex.<sup id="cite_ref-K&H_4-0" class="reference"><a href="#cite_note-K&H-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The uncatalyzed <a href="/wiki/Keto%E2%80%93enol_tautomerism" class="mw-redirect" title="Keto–enol tautomerism">keto–enol tautomerism</a> by a 1,3-hydrogen migration is forbidden by the <a href="/wiki/Woodward%E2%80%93Hoffmann_rules" title="Woodward–Hoffmann rules">Woodward–Hoffmann rules</a> and therefore has a high activation barrier and is not a significant pathway at or near room temperature. However, even trace amounts of acids or bases (including water) can catalyze the reaction. Even with rigorous precautions to minimize adventitious moisture or proton sources, vinyl alcohol can only be stored for minutes to hours before it isomerizes to acetaldehyde. (<a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a> is another example of a substance that is stable when rigorously pure, but decomposes rapidly due to catalysis by trace moisture.) </p><p>The tautomerization can also be catalyzed via photochemical process. These findings suggest that the keto–enol tautomerization is a viable route under atmospheric and stratospheric conditions, relevant to a role for vinyl alcohol in the production of organic acids in the atmosphere.<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><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> </p><p>Vinyl alcohol can be stabilized by controlling the water concentration in the system and utilizing the kinetic favorability of the <a href="/wiki/Deuterium" title="Deuterium">deuterium</a>-produced <a href="/wiki/Kinetic_isotope_effect" title="Kinetic isotope effect">kinetic isotope effect</a> (<i>k</i><sub>H<sup>+</sup></sub>/<i>k</i><sub>D<sup>+</sup></sub> = 4.75, <i>k</i><sub>H<sub>2</sub>O</sub>/<i>k</i><sub>D<sub>2</sub>O</sub> = 12). Deuterium stabilization can be accomplished through hydrolysis of a <a href="/wiki/Ketene" title="Ketene">ketene</a> precursor in the presence of a slight stoichiometric excess of <a href="/wiki/Heavy_water" title="Heavy water">heavy water</a> (D<sub>2</sub>O). Studies show that the tautomerization process is significantly inhibited at ambient temperatures ( <i>k</i><sub>t</sub> ≈ 10<sup>−6</sup> M/s), and the <a href="/wiki/Half-life" title="Half-life">half-life</a> of the enol form can easily be increased to <i>t</i><sub>1/2</sub> = 42 minutes for first-order hydrolysis kinetics.<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> <div class="mw-heading mw-heading2"><h2 id="Relationship_to_poly(vinyl_alcohol)"><span id="Relationship_to_poly.28vinyl_alcohol.29"></span>Relationship to poly(vinyl alcohol)</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinyl_alcohol&action=edit&section=3" title="Edit section: Relationship to poly(vinyl alcohol)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of the instability of vinyl alcohol, the <a href="/wiki/Thermoplastic" title="Thermoplastic">thermoplastic</a> <a href="/wiki/Polyvinyl_alcohol" title="Polyvinyl alcohol">polyvinyl alcohol</a> (PVA or PVOH) is made indirectly by polymerization of <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a> followed by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of the <a href="/wiki/Ester" title="Ester">ester</a> bonds (Ac = acetyl; HOAc = acetic acid):<sup id="cite_ref-Ullmann_8-0" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap"><i>n</i> CH<sub class="template-chem2-sub">2</sub>=CHOAc → (CH<sub class="template-chem2-sub">2</sub>−CHOAc)<sub class="template-chem2-sub"><i>n</i></sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>−CHOAc)<sub class="template-chem2-sub"><i>n</i></sub> + <i>n</i> H<sub class="template-chem2-sub">2</sub>O → (CH<sub class="template-chem2-sub">2</sub>−CHOH)<sub class="template-chem2-sub"><i>n</i></sub> + <i>n</i> HOAc</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="As_a_ligand">As a ligand</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinyl_alcohol&action=edit&section=4" title="Edit section: As a ligand"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several <a href="/wiki/Coordination_complex" title="Coordination complex">metal complexes</a> are known that contain vinyl alcohol as a <a href="/wiki/Ligand" title="Ligand">ligand</a>. One example is Pt(acac)(η<sup>2</sup>-C<sub>2</sub>H<sub>3</sub>OH)Cl.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence_in_interstellar_medium">Occurrence in interstellar medium</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vinyl_alcohol&action=edit&section=5" title="Edit section: Occurrence in interstellar medium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vinyl alcohol was detected in the <a href="/wiki/Molecular_cloud" title="Molecular cloud">molecular cloud</a> <a href="/wiki/Sagittarius_B2" title="Sagittarius B2">Sagittarius B</a> in 2001, the last of the three stable <a href="/wiki/Isomer" title="Isomer">isomers</a> of <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>O</span> (after acetaldehyde and <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>) to be detected in space.<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><sup id="cite_ref-SpaceVA_11-0" class="reference"><a href="#cite_note-SpaceVA-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Its stability in the (dilute) <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar medium</a> shows that its tautomerization does not happen <a href="/wiki/Molecularity" title="Molecularity">unimolecularly</a>,<sup id="cite_ref-SpaceVA_11-1" class="reference"><a href="#cite_note-SpaceVA-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> a fact attributed to the size of the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> barrier to the rearrangement being insurmountable at temperatures present in interstellar space.<sup id="cite_ref-ChemPhysChem2021_12-0" class="reference"><a href="#cite_note-ChemPhysChem2021-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The vinyl alcohol to acetaldehyde rearrangement is the only keto-enol tautomerisation to have been detected in deep space, induced by the provision of secondary electrons from <a href="/wiki/Galactic_cosmic_rays" class="mw-redirect" title="Galactic cosmic rays">galactic cosmic rays</a>.<sup id="cite_ref-ChemPhysChem2021_12-1" class="reference"><a href="#cite_note-ChemPhysChem2021-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </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=Vinyl_alcohol&action=edit&section=6" 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"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-March-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFSmithMarch2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, p. 101, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span 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.navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space800" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 1.5x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a class="mw-selflink selflink">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><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> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/17px-Earth-moon.jpg" decoding="async" width="17" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/26px-Earth-moon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/34px-Earth-moon.jpg 2x" data-file-width="3000" data-file-height="2400" /></span></span> </span><a href="/wiki/Portal:Outer_space" title="Portal:Outer space">Outer space portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/15px-Crab_Nebula.jpg" decoding="async" width="15" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/23px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/30px-Crab_Nebula.jpg 2x" 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rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Alcohols540" 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:Alcohols" title="Template:Alcohols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alcohols" title="Template talk:Alcohols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alcohols" title="Special:EditPage/Template:Alcohols"><abbr title="Edit 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<li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-Butyl alcohol</a></li> <li><a href="/wiki/Tryptophol" title="Tryptophol">Tryptophol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohols_(medicine)" title="Alcohols (medicine)">Medical alcohol</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/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li>Methanol poisoning <ul><li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxic_alcohol" class="mw-redirect" title="Toxic alcohol">Toxic alcohols</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/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</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/Primary_alcohol" title="Primary alcohol">Primary<br />alcohols</a> (1°)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methanol" title="Methanol">Methanol</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/4-Methylcyclohexanemethanol" title="4-Methylcyclohexanemethanol">4-Methylcyclohexanemethanol</a></li> <li><a href="/wiki/Aminomethanol" title="Aminomethanol">Aminomethanol</a></li> <li><a href="/wiki/Cyclohexylmethanol" title="Cyclohexylmethanol">Cyclohexylmethanol</a></li> <li><a href="/wiki/Methoxymethanol" title="Methoxymethanol">Methoxymethanol</a></li> <li><a href="/wiki/Methylazoxymethanol" title="Methylazoxymethanol">Methylazoxymethanol</a></li> <li><a href="/wiki/Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ethanol" title="Ethanol">Ethanol</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/1-Aminoethanol" title="1-Aminoethanol">1-Aminoethanol</a></li> <li><a href="/wiki/2,2,2-Trichloroethanol" title="2,2,2-Trichloroethanol">2,2,2-Trichloroethanol</a></li> <li><a href="/wiki/2,2,2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li> <li><a href="/wiki/2-(2-Ethoxyethoxy)ethanol" title="2-(2-Ethoxyethoxy)ethanol">2-(2-Ethoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-(2-Methoxyethoxy)ethanol" title="2-(2-Methoxyethoxy)ethanol">2-(2-Methoxyethoxy)ethanol</a></li> <li><a href="/wiki/2-Butoxyethanol" title="2-Butoxyethanol">2-Butoxyethanol</a></li> <li><a href="/wiki/2-Chloroethanol" title="2-Chloroethanol">2-Chloroethanol</a></li> <li><a href="/wiki/2-Ethoxyethanol" title="2-Ethoxyethanol">2-Ethoxyethanol</a></li> <li><a href="/wiki/2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li> <li><a href="/wiki/2-Mercaptoethanol" title="2-Mercaptoethanol">2-Mercaptoethanol</a></li> <li><a href="/wiki/2-Methoxyethanol" title="2-Methoxyethanol">2-Methoxyethanol</a></li> <li><a href="/wiki/Aminoethylethanolamine" title="Aminoethylethanolamine">Aminoethylethanolamine</a></li> <li><a href="/wiki/Diethylethanolamine" title="Diethylethanolamine">Diethylethanolamine</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Ethanolamine" title="Ethanolamine">Ethanolamine</a></li> <li><a href="/wiki/N,N-Diisopropylaminoethanol" title="N,N-Diisopropylaminoethanol"><i>N</i>,<i>N</i>-Diisopropylaminoethanol</a></li> <li><a href="/wiki/N-Methylethanolamine" title="N-Methylethanolamine"><i>N</i>-Methylethanolamine</a></li> <li><a href="/wiki/Phenoxyethanol" title="Phenoxyethanol">Phenoxyethanol</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Butanol" title="Butanol">Butanol</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/2-Methyl-1-butanol" title="2-Methyl-1-butanol">2-Methyl-1-butanol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol"><i>n</i>-Butanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>1</sub> — C<sub>9</sub></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/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">1-Propanol</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a></li> <li><a href="/wiki/1-Hexanol" title="1-Hexanol">1-Hexanol</a></li> <li><a href="/wiki/1-Heptanol" title="1-Heptanol">1-Heptanol</a></li> <li><a href="/wiki/1-Octanol" title="1-Octanol">1-Octanol</a> (capryl)</li> <li><a href="/wiki/1-Nonanol" title="1-Nonanol">1-Nonanol</a> (pelargonic)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>10</sub> — C<sub>19</sub></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/1-Decanol" title="1-Decanol">1-Decanol</a> (capric)</li> <li><a href="/wiki/1-Undecanol" class="mw-redirect" title="1-Undecanol">1-Undecanol</a> (hendecyl)</li> <li><a href="/wiki/1-Dodecanol" class="mw-redirect" title="1-Dodecanol">1-Dodecanol</a> (lauryl)</li> <li><a href="/wiki/1-Tridecanol" title="1-Tridecanol">1-Tridecanol</a></li> <li><a href="/wiki/1-Tetradecanol" title="1-Tetradecanol">1-Tetradecanol</a> (myristyl)</li> <li><a href="/wiki/1-Pentadecanol" title="1-Pentadecanol">1-Pentadecanol</a></li> <li><a href="/wiki/1-Hexadecanol" class="mw-redirect" title="1-Hexadecanol">1-Hexadecanol</a> (cetyl / palmityl)</li> <li><a href="/wiki/1-Heptadecanol" class="mw-redirect" title="1-Heptadecanol">1-Heptadecanol</a></li> <li><a href="/wiki/1-Octadecanol" class="mw-redirect" title="1-Octadecanol">1-Octadecanol</a> (stearyl)</li> <li><a href="/wiki/1-Nonadecanol" class="mw-redirect" title="1-Nonadecanol">1-Nonadecanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>20</sub> — C<sub>29</sub></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/1-Icosanol" class="mw-redirect" title="1-Icosanol">1-Icosanol</a> (arachidyl)</li> <li><a href="/wiki/1-Heneicosanol" title="1-Heneicosanol">1-Heneicosanol</a></li> <li><a href="/wiki/1-Docosanol" title="1-Docosanol">1-Docosanol</a> (behenyl)</li> <li><a href="/w/index.php?title=1-Tricosanol&action=edit&redlink=1" class="new" title="1-Tricosanol (page does not exist)">1-Tricosanol</a></li> <li><a href="/wiki/1-Tetracosanol" title="1-Tetracosanol">1-Tetracosanol</a> (lignoceryl)</li> <li><a href="/w/index.php?title=1-Pentacosanol&action=edit&redlink=1" class="new" title="1-Pentacosanol (page does not exist)">1-Pentacosanol</a></li> <li><a href="/wiki/1-Hexacosanol" title="1-Hexacosanol">1-Hexacosanol</a> (ceryl)</li> <li><a href="/wiki/1-Heptacosanol" title="1-Heptacosanol">1-Heptacosanol</a></li> <li><a href="/wiki/1-Octacosanol" title="1-Octacosanol">1-Octacosanol</a> (cluytyl / montanyl)</li> <li><a href="/wiki/1-Nonacosanol" title="1-Nonacosanol">1-Nonacosanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>30</sub> — C<sub>39</sub></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/1-Triacontanol" title="1-Triacontanol">1-Triacontanol</a> (melissyl / myricyl)</li> <li><a href="/w/index.php?title=1-Hentriacontanol&action=edit&redlink=1" class="new" title="1-Hentriacontanol (page does not exist)">1-Hentriacontanol</a></li> <li><a href="/wiki/1-Dotriacontanol" title="1-Dotriacontanol">1-Dotriacontanol</a> (lacceryl)</li> <li><a href="/w/index.php?title=1-Tritriacontanol&action=edit&redlink=1" class="new" title="1-Tritriacontanol (page does not exist)">1-Tritriacontanol</a></li> <li><a href="/w/index.php?title=1-Tetratriacontanol&action=edit&redlink=1" class="new" title="1-Tetratriacontanol (page does not exist)">1-Tetratriacontanol</a> (geddyl)</li> <li><a href="/w/index.php?title=1-Pentatriacontanol&action=edit&redlink=1" class="new" title="1-Pentatriacontanol (page does not exist)">1-Pentatriacontanol</a></li> <li><a href="/w/index.php?title=1-Hexatriacontanol&action=edit&redlink=1" class="new" title="1-Hexatriacontanol (page does not exist)">1-Hexatriacontanol</a></li> <li><a href="/w/index.php?title=1-Heptatriacontanol&action=edit&redlink=1" class="new" title="1-Heptatriacontanol (page does not exist)">1-Heptatriacontanol</a></li> <li><a href="/w/index.php?title=1-Octatriacontanol&action=edit&redlink=1" class="new" title="1-Octatriacontanol (page does not exist)">1-Octatriacontanol</a></li> <li><a href="/w/index.php?title=1-Nonatriacontanol&action=edit&redlink=1" class="new" title="1-Nonatriacontanol (page does not exist)">1-Nonatriacontanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Straight-chain<br />saturated<br />C<sub>40</sub> — C<sub>49</sub></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="/w/index.php?title=1-Tetracontanol&action=edit&redlink=1" class="new" title="1-Tetracontanol (page does not exist)">1-Tetracontanol</a></li> <li><a href="/w/index.php?title=1-Hentetracontanol&action=edit&redlink=1" class="new" title="1-Hentetracontanol (page does not exist)">1-Hentetracontanol</a></li> <li><a href="/w/index.php?title=1-Dotetracontanol&action=edit&redlink=1" class="new" title="1-Dotetracontanol (page does not exist)">1-Dotetracontanol</a></li> <li><a href="/w/index.php?title=1-Tritetracontanol&action=edit&redlink=1" class="new" title="1-Tritetracontanol (page does not exist)">1-Tritetracontanol</a></li> <li><a href="/w/index.php?title=1-Tetratetracontanol&action=edit&redlink=1" class="new" title="1-Tetratetracontanol (page does not exist)">1-Tetratetracontanol</a></li> <li><a href="/w/index.php?title=1-Pentatetracontanol&action=edit&redlink=1" class="new" title="1-Pentatetracontanol (page does not exist)">1-Pentatetracontanol</a></li> <li><a href="/w/index.php?title=1-Hexatetracontanol&action=edit&redlink=1" class="new" title="1-Hexatetracontanol (page does not exist)">1-Hexatetracontanol</a></li> <li><a href="/w/index.php?title=1-Heptatetracontanol&action=edit&redlink=1" class="new" title="1-Heptatetracontanol (page does not exist)">1-Heptatetracontanol</a></li> <li><a href="/w/index.php?title=1-Octatetracontanol&action=edit&redlink=1" class="new" title="1-Octatetracontanol (page does not exist)">1-Octatetracontanol</a></li> <li><a href="/w/index.php?title=1-Nonatetracontanol&action=edit&redlink=1" class="new" title="1-Nonatetracontanol (page does not exist)">1-Nonatetracontanol</a></li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/2-Ethylhexanol" title="2-Ethylhexanol">2-Ethylhexanol</a></li> <li><a href="/wiki/Allyl_alcohol" title="Allyl alcohol">Allyl alcohol</a></li> <li><a href="/wiki/Anisyl_alcohol" title="Anisyl alcohol">Anisyl alcohol</a></li> <li><a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li> <li><a href="/wiki/Cinnamyl_alcohol" title="Cinnamyl alcohol">Cinnamyl alcohol</a></li> <li><a href="/wiki/Crotyl_alcohol" title="Crotyl alcohol">Crotyl alcohol</a></li> <li><a href="/wiki/Furfuryl_alcohol" title="Furfuryl alcohol">Furfuryl alcohol</a></li> <li><a href="/wiki/Isoamyl_alcohol" title="Isoamyl alcohol">Isoamyl alcohol</a></li> <li><a href="/wiki/Neopentyl_alcohol" title="Neopentyl alcohol">Neopentyl alcohol</a></li> <li><a href="/wiki/Nicotinyl_alcohol" title="Nicotinyl alcohol">Nicotinyl alcohol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">Phenethyl alcohol</a></li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Propargyl_alcohol" title="Propargyl alcohol">Propargyl alcohol</a></li> <li><a href="/wiki/Salicyl_alcohol" title="Salicyl alcohol">Salicyl alcohol</a></li> <li><a href="/wiki/Tryptophol" title="Tryptophol">Tryptophol</a></li> <li><a href="/wiki/Vanillyl_alcohol" title="Vanillyl alcohol">Vanillyl alcohol</a></li> <li><a href="/wiki/Veratrole_alcohol" title="Veratrole alcohol">Veratrole alcohol</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Secondary<br /> alcohols (2°)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/1-Phenylethanol" title="1-Phenylethanol">1-Phenylethanol</a></li> <li><a href="/wiki/2-Butanol" title="2-Butanol">2-Butanol</a></li> <li><a href="/w/index.php?title=2-Deoxyerythritol&action=edit&redlink=1" class="new" title="2-Deoxyerythritol (page does not exist)">2-Deoxyerythritol</a></li> <li><a href="/wiki/2-Heptanol" title="2-Heptanol">2-Heptanol</a></li> <li><a href="/wiki/3-Heptanol" title="3-Heptanol">3-Heptanol</a></li> <li><a href="/wiki/2-Hexanol" title="2-Hexanol">2-Hexanol</a></li> <li><a href="/wiki/3-Hexanol" title="3-Hexanol">3-Hexanol</a></li> <li><a href="/wiki/3-Methyl-2-butanol" title="3-Methyl-2-butanol">3-Methyl-2-butanol</a></li> <li><a href="/wiki/2-Nonanol" title="2-Nonanol">2-Nonanol</a></li> <li><a href="/wiki/2-Octanol" title="2-Octanol">2-Octanol</a></li> <li><a href="/wiki/2-Pentanol" title="2-Pentanol">2-Pentanol</a></li> <li><a href="/wiki/3-Pentanol" title="3-Pentanol">3-Pentanol</a></li> <li><a href="/wiki/Cyclohexanol" title="Cyclohexanol">Cyclohexanol</a></li> <li><a href="/wiki/Cyclopentanol" title="Cyclopentanol">Cyclopentanol</a></li> <li><a href="/wiki/Cyclopropanol" title="Cyclopropanol">Cyclopropanol</a></li> <li><a href="/wiki/Diphenylmethanol" title="Diphenylmethanol">Diphenylmethanol</a></li> <li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropanol</a></li> <li><a href="/wiki/Pinacolyl_alcohol" title="Pinacolyl alcohol">Pinacolyl alcohol</a></li> <li><a href="/wiki/Pirkle%27s_alcohol" title="Pirkle's alcohol">Pirkle's alcohol</a></li> <li><a href="/wiki/Propylene_glycol_methyl_ether" title="Propylene glycol methyl ether">Propylene glycol methyl ether</a></li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tertiary<br /> alcohols (3°)</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/2-Methyl-2-pentanol" title="2-Methyl-2-pentanol">2-Methyl-2-pentanol</a></li> <li><a href="/w/index.php?title=2-Methylheptan-2-ol&action=edit&redlink=1" class="new" title="2-Methylheptan-2-ol (page does not exist)">2-Methylheptan-2-ol</a></li> <li><a href="/w/index.php?title=2-Methylhexan-2-ol&action=edit&redlink=1" class="new" title="2-Methylhexan-2-ol (page does not exist)">2-Methylhexan-2-ol</a></li> <li><a href="/wiki/3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li> <li><a href="/w/index.php?title=3-Methyloctan-3-ol&action=edit&redlink=1" class="new" title="3-Methyloctan-3-ol (page does not exist)">3-Methyloctan-3-ol</a></li> <li><a href="/wiki/Diacetone_alcohol" title="Diacetone alcohol">Diacetone alcohol</a></li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-<i>tert</i>-butyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol"><i>tert</i>-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-Butyl alcohol</a></li> <li><a href="/wiki/Triphenylethanol" title="Triphenylethanol">Triphenylethanol</a></li> <li><a href="/wiki/Triphenylmethanol" title="Triphenylmethanol">Triphenylmethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydric alcohols</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%">Monohydric alcohols</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/Methanol" title="Methanol">Methanol</a> (C<sub>1</sub>)</li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/1-Butanol" title="1-Butanol">1-Butanol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">1-Pentanol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Cetyl_alcohol" title="Cetyl alcohol">Cetyl alcohol</a> (C<sub>16</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dihydric alcohols</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/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trihydric alcohols</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/Glycerol" title="Glycerol">Glycerol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Polyhydric alcohols (sugar alcohols)</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/Pentaerythritol" title="Pentaerythritol">Pentaerythritol</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a>, <a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a>, <a href="/wiki/Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a>, <a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amyl_alcohol" title="Amyl alcohol">Amyl alcohols</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/2,2-Dimethylpropan-1-ol" class="mw-redirect" title="2,2-Dimethylpropan-1-ol">2,2-Dimethylpropan-1-ol </a></li> <li><a href="/wiki/2-Methylbutan-1-ol" class="mw-redirect" title="2-Methylbutan-1-ol">2-Methylbutan-1-ol </a></li> <li><a href="/wiki/2-Methylbutan-2-ol" class="mw-redirect" title="2-Methylbutan-2-ol">2-Methylbutan-2-ol </a></li> <li><a href="/wiki/3-Methylbutan-1-ol" class="mw-redirect" title="3-Methylbutan-1-ol">3-Methylbutan-1-ol </a></li> <li><a href="/wiki/3-Methylbutan-2-ol" class="mw-redirect" title="3-Methylbutan-2-ol">3-Methylbutan-2-ol </a></li> <li><a href="/wiki/Pentan-1-ol" class="mw-redirect" title="Pentan-1-ol">Pentan-1-ol </a></li> <li><a href="/wiki/Pentan-2-ol" class="mw-redirect" title="Pentan-2-ol">Pentan-2-ol </a></li> <li><a href="/wiki/Pentan-3-ol" class="mw-redirect" title="Pentan-3-ol">Pentan-3-ol </a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Aromatic alcohols</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/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a></li> <li><a href="/wiki/2,4-Dichlorobenzyl_alcohol" title="2,4-Dichlorobenzyl alcohol">2,4-Dichlorobenzyl alcohol</a></li> <li><a href="/wiki/3-Nitrobenzyl_alcohol" title="3-Nitrobenzyl alcohol">3-Nitrobenzyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Saturated<br /><a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</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/Cetostearyl_alcohol" title="Cetostearyl alcohol">Cetostearyl alcohol</a></li> <li><a href="/wiki/Decanol" class="mw-redirect" title="Decanol">Decanol</a></li> <li><a href="/wiki/Lauryl_alcohol" class="mw-redirect" title="Lauryl alcohol">Lauryl alcohol</a></li> <li><a href="/wiki/Myristyl_alcohol" class="mw-redirect" title="Myristyl alcohol">Myristyl alcohol</a></li> <li><a href="/wiki/Nonanol_(disambiguation)" class="mw-redirect mw-disambig" title="Nonanol (disambiguation)">Nonanol</a></li> <li><a href="/wiki/Octanol" title="Octanol">Octanol</a></li> <li><a href="/wiki/Tridecanol" class="mw-redirect" title="Tridecanol">Tridecanol</a></li> <li><a href="/wiki/Undecanol" title="Undecanol">Undecanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Branched and<br />unsaturated<br /><a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</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/3-Methyl-3-pentanol" title="3-Methyl-3-pentanol">3-Methyl-3-pentanol</a></li> <li><a href="/w/index.php?title=Erucyl_alcohol&action=edit&redlink=1" class="new" title="Erucyl alcohol (page does not exist)">Erucyl alcohol</a></li> <li><a href="/w/index.php?title=Linolenyl_alcohol&action=edit&redlink=1" class="new" title="Linolenyl alcohol (page does not exist)">Linolenyl alcohol</a></li> <li><a href="/wiki/Linoleyl_alcohol" title="Linoleyl alcohol">Linoleyl alcohol</a></li> <li><a href="/wiki/Oleyl_alcohol" title="Oleyl alcohol">Oleyl alcohol</a></li> <li><a href="/w/index.php?title=Palmitoleyl_alcohol&action=edit&redlink=1" class="new" title="Palmitoleyl alcohol (page does not exist)">Palmitoleyl alcohol</a></li> <li><a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">tert-Amyl alcohol</a></li> <li><a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol">tert-Butyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohols</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%">C<sub>1</sub> — C<sub>7</sub></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/Methylene_glycol" class="mw-redirect" title="Methylene glycol">Methylene glycol</a> (C<sub>1</sub>)</li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> (C<sub>2</sub>)</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> (C<sub>3</sub>)</li> <li><a href="/wiki/Erythritol" title="Erythritol">Erythritol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Threitol" title="Threitol">Threitol</a> (C<sub>4</sub>)</li> <li><a href="/wiki/Arabitol" title="Arabitol">Arabitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Ribitol" title="Ribitol">Ribitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Xylitol" title="Xylitol">Xylitol</a> (C<sub>5</sub>)</li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Galactitol" title="Galactitol">Galactitol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Iditol" title="Iditol">Iditol</a> (C<sub>6</sub>)</li> <li><a href="/wiki/Volemitol" title="Volemitol">Volemitol</a> (C<sub>7</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Deoxy sugar<br /> alcohols</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/Fucitol" title="Fucitol">Fucitol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cyclic sugar<br /> alcohols</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/Inositol" title="Inositol">Inositol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycylglycitols</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/Maltitol" title="Maltitol">Maltitol</a></li> <li><a href="/wiki/Lactitol" title="Lactitol">Lactitol</a></li> <li><a href="/wiki/Isomalt" title="Isomalt">Isomalt</a></li> <li><a href="/w/index.php?title=Maltotriitol&action=edit&redlink=1" class="new" title="Maltotriitol (page does not exist)">Maltotriitol</a></li> <li><a href="/w/index.php?title=Maltotetraitol&action=edit&redlink=1" class="new" title="Maltotetraitol (page does not exist)">Maltotetraitol</a></li> <li><a href="/w/index.php?title=Polyglycitol&action=edit&redlink=1" class="new" title="Polyglycitol (page does not exist)">Polyglycitol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Terpene alcohols</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%">Monoterpene<br /> alcohols</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/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Nerol" title="Nerol">Nerol</a></li> <li><a href="/wiki/Rhodinol" title="Rhodinol">Rhodinol</a></li> <li><a href="/wiki/Terpineol" title="Terpineol">Terpineol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquiterpene<br /> alcohols</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/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Farnesol" title="Farnesol">Farnesol</a></li> <li><a href="/wiki/Nerolidol" title="Nerolidol">Nerolidol</a></li> <li><a href="/wiki/Patchoulol" title="Patchoulol">Patchoulol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Diterpene<br /> alcohols</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/Phytol" title="Phytol">Phytol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Dialcohols</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/1,4-Butanediol" title="1,4-Butanediol">1,4-Butanediol</a></li> <li><a href="/wiki/1,5-Pentanediol" title="1,5-Pentanediol">1,5-Pentanediol</a></li> <li><a href="/wiki/2-Methyl-2-propyl-1,3-propanediol" title="2-Methyl-2-propyl-1,3-propanediol">2-Methyl-2-propyl-1,3-propanediol</a></li> <li><a href="/wiki/Diethylpropanediol" class="mw-redirect" title="Diethylpropanediol">Diethylpropanediol</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Trialcohols</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/Glycerol" title="Glycerol">Glycerol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sterols</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/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fluoroalcohol" title="Fluoroalcohol">Fluoroalcohols</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/1,3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol</a></li> <li><a href="/wiki/2,2,2-Trifluoroethanol" title="2,2,2-Trifluoroethanol">2,2,2-Trifluoroethanol</a></li> <li><a href="/wiki/2-Fluoroethanol" title="2-Fluoroethanol">2-Fluoroethanol</a></li> <li><a href="/wiki/Nonafluoro-tert-butyl_alcohol" title="Nonafluoro-tert-butyl alcohol">Nonafluoro-<i>tert</i>-butyl alcohol</a></li> <li><a href="/wiki/Trifluoromethanol" title="Trifluoromethanol">Trifluoromethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</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/Substitution_reaction" title="Substitution reaction">Substitution</a> of <a href="/wiki/Haloalkane#Substitution" title="Haloalkane">haloalkane</a></li> <li><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li> <li><a href="/wiki/Ether_cleavage" title="Ether cleavage">Ether cleavage</a></li> <li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of <a href="/wiki/Epoxide#Hydrolysis_and_addition_of_nucleophiles" title="Epoxide">epoxide</a></li> <li><a href="/wiki/Hydration_reaction" title="Hydration reaction">Hydration</a> of <a href="/wiki/Alkene#Hydration" title="Alkene">alkene</a></li> <li><a href="/wiki/Ziegler_process" title="Ziegler process">Ziegler process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</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/Deprotonation" title="Deprotonation">Deprotonation</a></li> <li><a href="/wiki/Protonation" title="Protonation">Protonation</a></li> <li><a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a> <ul><li><a href="/wiki/Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li></ul></li> <li><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a></li> <li><a href="/wiki/Fischer%E2%80%93Speier_esterification" title="Fischer–Speier esterification">Fischer–Speier esterification</a></li> <li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitution</a> of <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a></li> <li><a href="/wiki/Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a></li> <li><a href="/wiki/Nucleophilic_conjugate_addition" title="Nucleophilic conjugate addition">Nucleophilic conjugate addition</a></li> <li><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" 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> <a href="/wiki/Category:Alcohols" title="Category:Alcohols">Category</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" 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