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<li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Condensations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Condensations"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Condensations</span> </div> </a> <ul id="toc-Condensations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Coordination_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Coordination_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Coordination chemistry</span> </div> </a> <ul id="toc-Coordination_chemistry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biodegradation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biodegradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biodegradation</span> </div> </a> <ul id="toc-Biodegradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button 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Available in 29 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-29" 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">29 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B3%D9%8A%D8%AA%D9%8A%D9%84_%D8%A7%D9%84%D8%A3%D8%B3%D9%8A%D8%AA%D9%88%D9%86" title="أسيتيل الأسيتون – Arabic" lang="ar" hreflang="ar" data-title="أسيتيل الأسيتون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Asetilaseton" title="Asetilaseton – Azerbaijani" lang="az" hreflang="az" data-title="Asetilaseton" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%DB%8C%D9%84_%D8%A7%D8%B3%D8%AA%D9%88%D9%86" title="استیل استون – South Azerbaijani" lang="azb" hreflang="azb" data-title="استیل استون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Acetylaceton" title="Acetylaceton – Czech" lang="cs" hreflang="cs" data-title="Acetylaceton" 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/Acetylacetone" title="Acetylacetone – Danish" lang="da" hreflang="da" data-title="Acetylacetone" 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/Acetylaceton" title="Acetylaceton – German" lang="de" hreflang="de" data-title="Acetylaceton" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Acetilacetona" title="Acetilacetona – Spanish" lang="es" hreflang="es" data-title="Acetilacetona" 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/Acetilacetono" title="Acetilacetono – Esperanto" lang="eo" hreflang="eo" data-title="Acetilacetono" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%DB%8C%D9%84_%D8%A7%D8%B3%D8%AA%D9%88%D9%86" title="استیل استون – Persian" lang="fa" hreflang="fa" data-title="استیل استون" 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/Ac%C3%A9tylac%C3%A9tone" title="Acétylacétone – French" lang="fr" hreflang="fr" data-title="Acétylacétone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%8B%B8%EC%95%84%EC%84%B8%ED%86%A4" title="아세틸아세톤 – Korean" lang="ko" hreflang="ko" data-title="아세틸아세톤" 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/Asetilaseton" title="Asetilaseton – Indonesian" lang="id" hreflang="id" data-title="Asetilaseton" 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/Acetilacetone" title="Acetilacetone – Italian" lang="it" hreflang="it" data-title="Acetilacetone" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Acetilacetons" title="Acetilacetons – Latvian" lang="lv" hreflang="lv" data-title="Acetilacetons" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Acetilacetonas" title="Acetilacetonas – Lithuanian" lang="lt" hreflang="lt" data-title="Acetilacetonas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Acetylaceton" title="Acetylaceton – Dutch" lang="nl" hreflang="nl" data-title="Acetylaceton" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%BB%E3%83%81%E3%83%AB%E3%82%A2%E3%82%BB%E3%83%88%E3%83%B3" title="アセチルアセトン – Japanese" lang="ja" hreflang="ja" data-title="アセチルアセトン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Acetyloaceton" title="Acetyloaceton – Polish" lang="pl" hreflang="pl" data-title="Acetyloaceton" 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/Acetilacetona" title="Acetilacetona – Portuguese" lang="pt" hreflang="pt" data-title="Acetilacetona" 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/Acetilaceton%C4%83" title="Acetilacetonă – Romanian" lang="ro" hreflang="ro" data-title="Acetilacetonă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B0%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетилацетон – Russian" lang="ru" hreflang="ru" data-title="Ацетилацетон" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acetylacet%C3%B3n" title="Acetylacetón – Slovak" lang="sk" hreflang="sk" data-title="Acetylacetón" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Acetilaceton" title="Acetilaceton – Serbian" lang="sr" hreflang="sr" data-title="Acetilaceton" 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/Acetilaceton" title="Acetilaceton – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Acetilaceton" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Asetyyliasetoni" title="Asetyyliasetoni – Finnish" lang="fi" hreflang="fi" data-title="Asetyyliasetoni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Acetylaceton" title="Acetylaceton – Swedish" lang="sv" hreflang="sv" data-title="Acetylaceton" 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%85%E0%AE%9A%E0%AF%86%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%88%E0%AE%B2%E0%AF%8D_%E0%AE%85%E0%AE%9A%E0%AF%86%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="அசெட்டைல் அசெட்டோன் – Tamil" lang="ta" hreflang="ta" data-title="அசெட்டைல் அசெட்டோன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B0%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетилацетон – Ukrainian" lang="uk" hreflang="uk" data-title="Ацетилацетон" 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%E9%85%B0%E4%B8%99%E9%85%AE" title="乙酰丙酮 – Chinese" lang="zh" hreflang="zh" data-title="乙酰丙酮" 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/Q413447#sitelinks-wikipedia" 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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">"Acac" redirects here. For other uses, see <a href="/wiki/ACAC_(disambiguation)" class="mw-redirect mw-disambig" title="ACAC (disambiguation)">ACAC (disambiguation)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Acetylacetone </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetyloaceton.svg" class="mw-file-description" title="Skeletal structures of both tautomers"><img alt="Skeletal structures of both tautomers" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acetyloaceton.svg/150px-Acetyloaceton.svg.png" decoding="async" width="150" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acetyloaceton.svg/225px-Acetyloaceton.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acetyloaceton.svg/300px-Acetyloaceton.svg.png 2x" data-file-width="180" data-file-height="91" /></a></span> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of the enol tautomer"><img alt="Ball-and-stick model of the enol tautomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png/110px-Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png" decoding="async" width="110" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png/165px-Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png/220px-Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-balls.png 2x" data-file-width="2000" data-file-height="1223" /></a><figcaption>Ball-and-stick model of the enol tautomer</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of the keto tautomer"><img alt="Ball-and-stick model of the keto tautomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png/110px-Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png" decoding="async" width="110" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png/165px-Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png/220px-Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-balls.png 2x" data-file-width="2000" data-file-height="1188" /></a><figcaption>Ball-and-stick model of the keto tautomer</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png" class="mw-file-description" title="Space-filling model of the enol tautomer"><img alt="Space-filling model of the enol tautomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png/110px-Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png" decoding="async" width="110" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png/165px-Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png/220px-Acetylacetone-enol-tautomer-from-xtal-Mercury-3D-sf.png 2x" data-file-width="2000" data-file-height="1387" /></a><figcaption>Space-filling model of the enol tautomer</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png" class="mw-file-description" title="Space-filling model of the keto tautomer"><img alt="Space-filling model of the keto tautomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png/110px-Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png" decoding="async" width="110" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png/165px-Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/08/Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png/220px-Acetylacetone-keto-tautomer-from-xtal-Mercury-3D-sf.png 2x" data-file-width="2000" data-file-height="1378" /></a><figcaption>Space-filling model of the keto tautomer</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC names</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(3Z)-4-Hydroxy-3-penten-2-one <i>(enol form)</i><br />Pentane-2,4-dione <i>(keto form)</i></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Hacac</li><li>2,4-Pentanedione</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=123-54-6">123-54-6</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=O%3DC%28C%29CC%28%3DO%29C">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29CC%28%3DO%29C">Interactive image</a></span></li><li><a href="/wiki/File:Acetylacetone_keto-enol_tautomerism.svg" title="File:Acetylacetone keto-enol tautomerism.svg">Enol form</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28O%29%3DCC%28%3DO%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>741937 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=14750">CHEBI:14750</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL191625">ChEMBL191625</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.29001.html">29001</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/100.004.214">100.004.214</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q413447#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>204-634-0</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>2537 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C15499">C15499</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/31261">31261</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>SA1925000</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/46R950BP4J">46R950BP4J</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>2310 </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/DTXSID4021979">DTXSID4021979</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q413447#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3<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: YRKCREAYFQTBPV-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YRKCREAYFQTBPV-UHFFFAOYAO</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(C)CC(=O)C</div></li><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%;">CC(=O)CC(=O)C</div></li><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%;"><a href="/wiki/File:Acetylacetone_keto-enol_tautomerism.svg" title="File:Acetylacetone keto-enol tautomerism.svg">Enol form</a>: CC(O)=CC(=O)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>5</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002100117000000000♠"></span>100.117</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless liquid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.975 g/mL<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−23 °C (−9 °F; 250 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>140 °C (284 °F; 413 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>16 g/(100 mL) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−54.88·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H226: Flammable liquid and vapour">H226</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H311: Toxic in contact with skin">H311</abbr>, <abbr class="abbr" title="H320: Causes eye irritation">H320</abbr>, <abbr class="abbr" title="H331: Toxic if inhaled">H331</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H341: Suspected of causing genetic defects">H341</abbr>, <abbr class="abbr" title="H370: Causes damage to organs">H370</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P202: Do not handle until all safety precautions have been read and understood.">P202</abbr>, <abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P307+P311: IF exposed: Call a POISON CENTER or doctor/physician.">P307+P311</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P311: Call a POISON CENTER or doctor/physician.">P311</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P322: Specific measures (see ... on this label).">P322</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P361: Remove/Take off immediately all contaminated clothing.">P361</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_f39ae6e266e5d33a" /></span><map name="ImageMap_f39ae6e266e5d33a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>34 °C (93 °F; 307 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>340 °C (644 °F; 613 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>2.4–11.6% </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477240155&page2=Acetylacetone">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>Acetylacetone</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the chemical formula <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">CH<sub class="template-chem2-sub">3</sub>−C(=O)−CH<sub class="template-chem2-sub">2</sub>−C(=O)−CH<sub class="template-chem2-sub">3</sub></span>. It is classified as a 1,3-<a href="/wiki/Diketone" class="mw-redirect" title="Diketone">diketone</a>. It exists in equilibrium with a <a href="/wiki/Tautomer" title="Tautomer">tautomer</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C(=O)−CH=C(−OH)−CH<sub class="template-chem2-sub">3</sub></span>. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications.<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> Acetylacetone is a building block for the synthesis of many <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a> as well as <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic compounds</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Tautomerism">Tautomerism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=2" title="Edit section: Tautomerism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" style="float: left; margin: 1em;"> <tbody><tr> <th>Solvent</th> <th><i>K</i><sub>keto→enol</sub> </th></tr> <tr> <td><a href="/wiki/Gas" title="Gas">Gas phase</a></td> <td>11.7 </td></tr> <tr> <td><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></td> <td>42 </td></tr> <tr> <td><a href="/wiki/Toluene" title="Toluene">Toluene</a></td> <td>10 </td></tr> <tr> <td><a href="/wiki/THF" class="mw-redirect" title="THF">THF</a></td> <td>7.2 </td></tr> <tr> <td><a href="/wiki/Deuterated_chloroform" title="Deuterated chloroform"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CDCl<sub class="template-chem2-sub">3</sub></span></a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td> <td>5.7 </td></tr> <tr> <td><a href="/wiki/DMSO" class="mw-redirect" title="DMSO">DMSO</a></td> <td>2 </td></tr> <tr> <td><a href="/wiki/Water" title="Water">Water</a></td> <td>0.23 </td></tr></tbody></table> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetylaceton-Tautomerie.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Acetylaceton-Tautomerie.svg/347px-Acetylaceton-Tautomerie.svg.png" decoding="async" width="347" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Acetylaceton-Tautomerie.svg/521px-Acetylaceton-Tautomerie.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Acetylaceton-Tautomerie.svg/694px-Acetylaceton-Tautomerie.svg.png 2x" data-file-width="520" data-file-height="121" /></a><figcaption></figcaption></figure> <p>The <a href="/wiki/Keto%E2%80%93enol_tautomerism" class="mw-redirect" title="Keto–enol tautomerism">keto and enol</a> <a href="/wiki/Tautomers" class="mw-redirect" title="Tautomers">tautomers</a> of acetylacetone coexist in solution. The enol form has C<sub>2v</sub> <a href="/wiki/Molecular_symmetry" title="Molecular symmetry">symmetry</a>, meaning the hydrogen atom is shared equally between the two oxygen atoms.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In the gas phase, the <a href="/wiki/Equilibrium_constant" title="Equilibrium constant">equilibrium constant</a>, <i>K</i><sub>keto→enol</sub>, is 11.7, favoring the enol form. The two tautomeric forms can be distinguished by <a href="/wiki/NMR_spectroscopy" class="mw-redirect" title="NMR spectroscopy">NMR spectroscopy</a>, <a href="/wiki/IR_spectroscopy" class="mw-redirect" title="IR spectroscopy">IR spectroscopy</a> and other methods.<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> The equilibrium constant tends to be high in nonpolar solvents; when <i>K</i><sub>keto→enol</sub> is equal or greater than 1, the enol form is favoured. The keto form becomes more favourable in polar, hydrogen-bonding solvents, such as water.<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> The enol form is a <a href="/wiki/Vinylogous" class="mw-redirect" title="Vinylogous">vinylogous</a> analogue of a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (May 2024)">citation needed</span></a></i>]</sup></p><div style="clear:left;" class=""></div> <div class="mw-heading mw-heading3"><h3 id="Acid–base_properties"><span id="Acid.E2.80.93base_properties"></span>Acid–base properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=3" title="Edit section: Acid–base properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" style="float: left; margin: 1em;"> <tbody><tr> <th>Solvent</th> <th>T/°C</th> <th>p<i>K</i><sub>a</sub><sup id="cite_ref-scdb_8-0" class="reference"><a href="#cite_note-scdb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td>40% <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>/water</td> <td>30</td> <td>9.8 </td></tr> <tr> <td>70% <a href="/wiki/Dioxane" class="mw-redirect" title="Dioxane">dioxane</a>/water</td> <td>28</td> <td>12.5 </td></tr> <tr> <td>80% <a href="/wiki/DMSO" class="mw-redirect" title="DMSO">DMSO</a>/water</td> <td>25</td> <td>10.16 </td></tr> <tr> <td>DMSO</td> <td>25</td> <td>13.41 </td></tr></tbody></table> <p>Acetylacetone is a <a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">weak acid</a>. It forms the acetylacetonate <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">7</sub>O<span class="template-chem2-su"><span>−</span><span>2</span></span></span> (commonly abbreviated <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">acac<sup class="template-chem2-sup">−</sup></span></b>): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">8</sub>O<sub class="template-chem2-sub">2</sub> ⇌ C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">7</sub>O<span class="template-chem2-su"><span>−</span><span>2</span></span> + H<sup class="template-chem2-sup">+</sup></span></dd></dl> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Acetylacetonate_anion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Acetylacetonate_anion.png/200px-Acetylacetonate_anion.png" decoding="async" width="200" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Acetylacetonate_anion.png/300px-Acetylacetonate_anion.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Acetylacetonate_anion.png/400px-Acetylacetonate_anion.png 2x" data-file-width="1200" data-file-height="643" /></a><figcaption>The structure of the acetylacetonate anion (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">acac<sup class="template-chem2-sup">−</sup></span>)</figcaption></figure> <p>In the acetylacetonate anion, both <a href="/wiki/Carbon" title="Carbon">C</a>-<a href="/wiki/Oxygen" title="Oxygen">O</a> bonds are equivalent. Both C-C central bonds are equivalent as well, with one <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom bonded to the central carbon atom (the <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">C3 atom</a>). Those two equivalencies are because there is a <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a> between the four bonds in the <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">O-C2-C3-C4-O linkage</a> in the acetylacetonate anion, where the <a href="/wiki/Bond_order" title="Bond order">bond order</a> of those four bonds is about 1.5. Both <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atoms equally share the <a href="/wiki/Negative_charge" class="mw-redirect" title="Negative charge">negative charge</a>. The acetylacetonate anion is a <a href="/wiki/Bidentate" class="mw-redirect" title="Bidentate">bidentate</a> <a href="/wiki/Ligand" title="Ligand">ligand</a>. </p> <p><a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> recommended <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> values for this equilibrium in aqueous solution at 25 °C are 8.99 ± 0.04 (<i>I</i> = 0), 8.83 ± 0.02 (<i>I</i> = 0.1 <a href="/wiki/Molar_concentration" title="Molar concentration">M</a> <a href="/wiki/Sodium_perchlorate" title="Sodium perchlorate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaClO<sub class="template-chem2-sub">4</sub></span></a>) and 9.00 ± 0.03 (<i>I</i> = 1.0 M <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaClO<sub class="template-chem2-sub">4</sub></span>; <i>I</i> = <a href="/wiki/Ionic_strength" title="Ionic strength">Ionic strength</a>).<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Values for mixed solvents are available. Very strong <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a>, such as <a href="/wiki/Organolithium" class="mw-redirect" title="Organolithium">organolithium</a> compounds, will <a href="/wiki/Deprotonate" class="mw-redirect" title="Deprotonate">deprotonate</a> acetylacetone twice. The resulting dilithium species can then be <a href="/wiki/Alkylated" class="mw-redirect" title="Alkylated">alkylated</a> at the <a href="/wiki/Carbon" title="Carbon">carbon</a> atom at the <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">position 1</a>.</p><div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=4" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylacetone is prepared industrially by the thermal rearrangement of <a href="/wiki/Isopropenyl_acetate" title="Isopropenyl acetate">isopropenyl acetate</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Acetylacetone_synthesis01.svg" class="mw-file-description" title="Synthese von Acetylaceton"><img alt="Synthese von Acetylaceton" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Acetylacetone_synthesis01.svg/455px-Acetylacetone_synthesis01.svg.png" decoding="async" width="455" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Acetylacetone_synthesis01.svg/683px-Acetylacetone_synthesis01.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Acetylacetone_synthesis01.svg/910px-Acetylacetone_synthesis01.svg.png 2x" data-file-width="534" data-file-height="96" /></a></span> </p><p>Laboratory routes to acetylacetone also begin with <a href="/wiki/Acetone" title="Acetone">acetone</a>. Acetone and <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>C(O))<sub class="template-chem2-sub">2</sub>O</span>) upon the addition of <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BF<sub class="template-chem2-sub">3</sub></span>) catalyst:<sup id="cite_ref-denoon_11-0" class="reference"><a href="#cite_note-denoon-11"><span class="cite-bracket">[</span>11<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">(CH<sub class="template-chem2-sub">3</sub>C(O))<sub class="template-chem2-sub">2</sub>O + CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">3</sub> → CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>C(O)CH<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>A second synthesis involves the base-catalyzed condensation (e.g., by <a href="/wiki/Sodium_ethoxide" title="Sodium ethoxide">sodium ethoxide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>O<sup class="template-chem2-sup">−</sup>Na<sup class="template-chem2-sup">+</sup></span>) of acetone and <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a>, followed by acidification of the <a href="/wiki/Sodium_acetylacetonate" title="Sodium acetylacetonate">sodium acetylacetonate</a> (e.g., by <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> HCl):<sup id="cite_ref-denoon_11-1" class="reference"><a href="#cite_note-denoon-11"><span class="cite-bracket">[</span>11<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">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>O<sup class="template-chem2-sup">−</sup>Na<sup class="template-chem2-sup">+</sup> + CH<sub class="template-chem2-sub">3</sub>C(O)OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> + CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">3</sub> → Na<sup class="template-chem2-sup">+</sup>[CH<sub class="template-chem2-sub">3</sub>C(O)CHC(O<sup class="template-chem2-sup">−</sup>)CH<sub class="template-chem2-sub">3</sub>] + 2 CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sup class="template-chem2-sup">+</sup>[CH<sub class="template-chem2-sub">3</sub>C(O)CHC(O<sup class="template-chem2-sup">−</sup>)CH<sub class="template-chem2-sub">3</sub>] + HCl → CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>C(O)CH<sub class="template-chem2-sub">3</sub> + NaCl</span></dd></dl> <p>Because of the ease of these syntheses, many analogues of acetylacetonates are known. Some examples are <a href="/wiki/Benzoylacetone" title="Benzoylacetone">benzoylacetone</a>, <a href="/wiki/Dibenzoylmethane" title="Dibenzoylmethane">dibenzoylmethane</a> (dbaH)<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The abbreviation for dibenzoylmethane is "DBM", not "dbaH". Am I missing something? (November 2023)">clarification needed</span></a></i>]</sup> and <a href="/wiki/Butyl_group" title="Butyl group"><i>tert</i>-butyl</a> analogue <a href="/w/index.php?title=2,2,6,6-tetramethyl-3,5-heptanedione&action=edit&redlink=1" class="new" title="2,2,6,6-tetramethyl-3,5-heptanedione (page does not exist)">2,2,6,6-tetramethyl-3,5-heptanedione</a>. <a href="/wiki/Trifluoroacetylacetone" class="mw-redirect" title="Trifluoroacetylacetone">Trifluoroacetylacetone</a> and <a href="/wiki/Hexafluoroacetylacetonate" class="mw-redirect" title="Hexafluoroacetylacetonate">hexafluoroacetylacetonate</a> are also used to generate volatile <a href="/wiki/Metal_complex" class="mw-redirect" title="Metal complex">metal complexes</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=5" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Condensations">Condensations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=6" title="Edit section: Condensations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylacetone is a versatile bifunctional precursor to heterocycles because both keto groups may undergo <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation</a>. For example, condensation with <a href="/wiki/Hydrazine" title="Hydrazine">Hydrazine</a> produces <a href="/wiki/Pyrazole" title="Pyrazole">pyrazoles</a> while condensation with <a href="/wiki/Urea" title="Urea">Urea</a> provides <a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidines</a>. Condensation with two aryl- or alkylamines gives <a href="/wiki/NacNac" title="NacNac">NacNacs</a>, wherein the oxygen atoms in acetylacetone are replaced by NR (R = aryl, alkyl). </p> <div class="mw-heading mw-heading3"><h3 id="Coordination_chemistry">Coordination chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=7" title="Edit section: Coordination chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Metal_acetylacetonates" title="Metal acetylacetonates">Metal acetylacetonates</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Vanadyl-acetylacetonate-from-xtal-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Vanadyl-acetylacetonate-from-xtal-3D-balls.png/200px-Vanadyl-acetylacetonate-from-xtal-3D-balls.png" decoding="async" width="200" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Vanadyl-acetylacetonate-from-xtal-3D-balls.png/300px-Vanadyl-acetylacetonate-from-xtal-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Vanadyl-acetylacetonate-from-xtal-3D-balls.png/400px-Vanadyl-acetylacetonate-from-xtal-3D-balls.png 2x" data-file-width="1100" data-file-height="723" /></a><figcaption>A <a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">ball-and-stick model</a> of VO(acac)<sub>2</sub></figcaption></figure> <p><a href="/wiki/Sodium_acetylacetonate" title="Sodium acetylacetonate">Sodium acetylacetonate</a>, Na(acac), is the precursor to many <a href="/wiki/Acetylacetonate_complex" class="mw-redirect" title="Acetylacetonate complex">acetylacetonate complexes</a>. A general method of synthesis is to treat a metal salt with acetylacetone in the presence of a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>:<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MB<sub class="template-chem2-sub"><i>z</i></sub> + <i>z</i> Hacac ⇌ M(acac)<sub class="template-chem2-sub"><i>z</i></sub> + <i>z</i> BH</span></dd></dl> <p>Both oxygen atoms bind to the metal to form a six-membered chelate ring. In some cases the <a href="/wiki/Chelate_effect" class="mw-redirect" title="Chelate effect">chelate effect</a> is so strong that no added base is needed to form the complex. </p> <div class="mw-heading mw-heading2"><h2 id="Biodegradation">Biodegradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=8" title="Edit section: Biodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The enzyme <a href="/wiki/Acetylacetone-cleaving_enzyme" title="Acetylacetone-cleaving enzyme">acetylacetone dioxygenase</a> cleaves the carbon-carbon bond of acetylacetone, producing acetate and <a href="/wiki/Methylglyoxal" title="Methylglyoxal">2-oxopropanal</a>. The enzyme is <a href="/wiki/Iron(II)" class="mw-redirect" title="Iron(II)">iron(II)</a>-dependent, but it has been proven to bind to <a href="/wiki/Zinc" title="Zinc">zinc</a> as well. Acetylacetone degradation has been characterized in the bacterium <i><a href="/wiki/Acinetobacter_johnsonii" class="mw-redirect" title="Acinetobacter johnsonii">Acinetobacter johnsonii</a></i>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">8</sub>O<sub class="template-chem2-sub">2</sub> + <a href="/wiki/Oxygen" title="Oxygen">O<sub class="template-chem2-sub">2</sub></a> → <a href="/wiki/Acetic_acid" title="Acetic acid">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">2</sub></a> + <a href="/wiki/Methylglyoxal" title="Methylglyoxal">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">2</sub></a></span></dd></dl> <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=Acetylacetone&action=edit&section=9" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/sial/05581?lang=en&region=GB">"05581: Acetylacetone"</a>. <i>Sigma-Aldrich</i>.</cite><span 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O.</a> (1982). <a rel="nofollow" class="external text" href="http://www.iupac.org/publications/pac/pdf/1982/pdf/5412x2557.pdf">"Critical evaluation of equilibrium constants involving acetylacetone and its metal chelates"</a> <span class="cs1-format">(PDF)</span>. <i>Pure and Applied Chemistry</i>. <b>54</b> (12): 2557–2592. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac198254122557">10.1351/pac198254122557</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:96848983">96848983</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+and+Applied+Chemistry&rft.atitle=Critical+evaluation+of+equilibrium+constants+involving+acetylacetone+and+its+metal+chelates&rft.volume=54&rft.issue=12&rft.pages=2557-2592&rft.date=1982&rft_id=info%3Adoi%2F10.1351%2Fpac198254122557&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A96848983%23id-name%3DS2CID&rft.aulast=Stary&rft.aufirst=J.&rft.au=Liljenzin%2C+J.+O.&rft_id=http%3A%2F%2Fwww.iupac.org%2Fpublications%2Fpac%2Fpdf%2F1982%2Fpdf%2F5412x2557.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylacetone" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSiegelEggersdorfer2002" class="citation encyclopaedia cs1">Siegel, Hardo; Eggersdorfer, Manfred (2002). 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Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a15_077">10.1002/14356007.a15_077</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527306732" title="Special:BookSources/9783527306732"><bdi>9783527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ketones&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2002&rft_id=info%3Adoi%2F10.1002%2F14356007.a15_077&rft.isbn=9783527306732&rft.aulast=Siegel&rft.aufirst=Hardo&rft.au=Eggersdorfer%2C+Manfred&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylacetone" class="Z3988"></span></span> </li> <li id="cite_note-denoon-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-denoon_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-denoon_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDenoonAdkinsRainey1940" class="citation journal cs1">Denoon, C. E. Jr.; Adkins, Homer; Rainey, James L. (1940). "Acetylacetone". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>20</b>: 6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.020.0006">10.15227/orgsyn.020.0006</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Acetylacetone&rft.volume=20&rft.pages=6&rft.date=1940&rft_id=info%3Adoi%2F10.15227%2Forgsyn.020.0006&rft.aulast=Denoon&rft.aufirst=C.+E.+Jr.&rft.au=Adkins%2C+Homer&rft.au=Rainey%2C+James+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylacetone" class="Z3988"></span>.</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFO'Brien" class="citation web cs1">O'Brien, Brian. <a rel="nofollow" class="external text" href="http://homepages.gac.edu/~bobrien/Inorganic_Lab/acac/Co.tfa.3.&.Co.acac.3.handout.S01.pdf">"Co(tfa)<sub>3</sub> & Co(acac)<sub>3</sub> handout"</a> <span class="cs1-format">(PDF)</span>. Gustavus Adolphus College.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Co%28tfa%29%3Csub%3E3%3C%2Fsub%3E+%26+Co%28acac%29%3Csub%3E3%3C%2Fsub%3E+handout&rft.pub=Gustavus+Adolphus+College&rft.aulast=O%27Brien&rft.aufirst=Brian&rft_id=http%3A%2F%2Fhomepages.gac.edu%2F~bobrien%2FInorganic_Lab%2Facac%2FCo.tfa.3.%26.Co.acac.3.handout.S01.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylacetone" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStraganzGliederBreckerRibbons2003" class="citation journal cs1">Straganz, G.D.; Glieder, A.; Brecker, L.; Ribbons, D.W.; Steiner, W. (2003). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1223103">"Acetylacetone-cleaving enzyme Dke1: a novel C–C-bond-cleaving enzyme from<i> Acinetobacter johnsonii</i>"</a>. <i>Biochemical Journal</i>. <b>369</b> (3): 573–581. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1042%2FBJ20021047">10.1042/BJ20021047</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1223103">1223103</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12379146">12379146</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+Journal&rft.atitle=Acetylacetone-cleaving+enzyme+Dke1%3A+a+novel+C%E2%80%93C-bond-cleaving+enzyme+from+Acinetobacter+johnsonii&rft.volume=369&rft.issue=3&rft.pages=573-581&rft.date=2003&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1223103%23id-name%3DPMC&rft_id=info%3Apmid%2F12379146&rft_id=info%3Adoi%2F10.1042%2FBJ20021047&rft.aulast=Straganz&rft.aufirst=G.D.&rft.au=Glieder%2C+A.&rft.au=Brecker%2C+L.&rft.au=Ribbons%2C+D.W.&rft.au=Steiner%2C+W.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1223103&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylacetone" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylacetone&action=edit&section=10" title="Edit 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title="Special:EditPage/Template:Acetylacetonate complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Metal_acetylacetonate_complexes" style="font-size:114%;margin:0 4em"><a href="/wiki/Metal_acetylacetonate" class="mw-redirect" title="Metal acetylacetonate">Metal acetylacetonate</a> complexes</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a class="mw-selflink selflink">H(acac)</a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td>Li </td> <td>Be </td> <td>B </td> <td>C </td> <td>N </td> <td>O </td> <td>F </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_acetylacetonate" title="Sodium acetylacetonate">Na(acac)</a> </td> <td>Mg </td> <td><a href="/wiki/Aluminium_acetylacetonate" title="Aluminium acetylacetonate">Al(acac)<sub>3</sub></a> </td> <td>Si </td> <td>P </td> <td>S </td> <td>Cl </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td>K </td> <td>Ca </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Scandium_acetylacetonate" title="Scandium acetylacetonate">Sc(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Titanium_bis(acetylacetonate)dichloride" title="Titanium bis(acetylacetonate)dichloride">Ti(acac)<sub>2</sub>Cl<sub>2</sub></a><br /> <a href="/wiki/Tris(acetylacetonato)titanium(III)" title="Tris(acetylacetonato)titanium(III)">Ti(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Vanadium(III)_acetylacetonate" title="Vanadium(III) acetylacetonate">V(acac)<sub>3</sub></a><br /> <a href="/wiki/Vanadyl_acetylacetonate" title="Vanadyl acetylacetonate">VO(acac)<sub>2</sub></a> </td> <td><a href="/wiki/Chromium(II)_acetylacetonate" title="Chromium(II) acetylacetonate">Cr(acac)<sub>2</sub></a><br /> <a href="/wiki/Chromium(III)_acetylacetonate" title="Chromium(III) acetylacetonate">Cr(acac)<sub>3</sub></a> </td> <td>Mn </td> <td><a href="/wiki/Bis(acetylacetonato)iron(II)" title="Bis(acetylacetonato)iron(II)">Fe(acac)<sub>2</sub></a><br /><a href="/wiki/Tris(acetylacetonato)iron(III)" title="Tris(acetylacetonato)iron(III)">Fe(acac)<sub>3</sub></a> </td> <td><a href="/w/index.php?title=Bis(acetylacetonato)cobalt(II)&action=edit&redlink=1" class="new" title="Bis(acetylacetonato)cobalt(II) (page does not exist)">Co(acac)<sub>2</sub></a><br /><a href="/wiki/Tris(acetylacetonato)cobalt(III)" title="Tris(acetylacetonato)cobalt(III)">Co(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Nickel(II)_bis(acetylacetonate)" title="Nickel(II) bis(acetylacetonate)">[Ni(acac)<sub>2</sub>]<sub>3</sub></a> </td> <td><a href="/wiki/Copper(II)_acetylacetonate" title="Copper(II) acetylacetonate">Cu(acac)<sub>2</sub></a> </td> <td><a href="/wiki/Zinc_acetylacetonate" title="Zinc acetylacetonate">Zn(acac)<sub>2</sub></a> </td> <td><a href="/wiki/Gallium_acetylacetonate" title="Gallium acetylacetonate">Ga(acac)<sub>3</sub></a> </td> <td>Ge </td> <td>As </td> <td>Se </td> <td>Br </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td>Rb </td> <td>Sr </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Yttrium_acetylacetonate" title="Yttrium acetylacetonate">Y(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Zirconium_acetylacetonate" title="Zirconium acetylacetonate">Zr(acac)<sub>4</sub></a> </td> <td>Nb </td> <td><a href="/w/index.php?title=Dioxymolybdenum_acetate&action=edit&redlink=1" class="new" title="Dioxymolybdenum acetate (page does not exist)">MoO<sub>2</sub>(acac)<sub>2</sub></a> </td> <td>Tc </td> <td><a href="/wiki/Ruthenium(III)_acetylacetonate" title="Ruthenium(III) acetylacetonate">Ru(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Dicarbonyl(acetylacetonato)rhodium(I)" title="Dicarbonyl(acetylacetonato)rhodium(I)">Rh(acac)(CO)<sub>2</sub></a><br /> <a href="/wiki/Rhodium_acetylacetonate" title="Rhodium acetylacetonate">Rh(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Palladium(II)_bis(acetylacetonate)" title="Palladium(II) bis(acetylacetonate)">Pd(acac)<sub>2</sub></a> </td> <td>Ag </td> <td>Cd </td> <td><a href="/wiki/Indium_acetylacetonate" title="Indium acetylacetonate">In(acac)<sub>3</sub></a> </td> <td>Sn </td> <td>Sb </td> <td>Te </td> <td>I </td> <td>Xe </td></tr> <tr style="background-color:mistyrose"> <td>Cs </td> <td><a href="/wiki/Barium_acetylacetonate" title="Barium acetylacetonate">Ba(acac)<sub>2</sub></a> </td> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lutetium_acetylacetonate" title="Lutetium acetylacetonate">Lu(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Hafnium_acetylacetonate" title="Hafnium acetylacetonate">Hf(acac)<sub>4</sub></a> </td> <td>Ta </td> <td>W </td> <td>Re </td> <td>Os </td> <td><a href="/wiki/Iridium_acetylacetonate" title="Iridium acetylacetonate">Ir(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Platinum(II)_bis(acetylacetonate)" title="Platinum(II) bis(acetylacetonate)">Pt(acac)<sub>2</sub></a> </td> <td>Au </td> <td>Hg </td> <td><a href="/w/index.php?title=Thallium(I)_acetylacetonate&action=edit&redlink=1" class="new" title="Thallium(I) acetylacetonate (page does not exist)">Tl(acac)</a> </td> <td>Pb </td> <td>Bi </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanum_acetylacetonate" title="Lanthanum acetylacetonate">La(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Cerium(III)_acetylacetonate" title="Cerium(III) acetylacetonate">Ce(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Praseodymium_acetylacetonate" title="Praseodymium acetylacetonate">Pr(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Neodymium_acetylacetonate" class="mw-redirect" title="Neodymium acetylacetonate">Nd(acac)<sub>3</sub></a> </td> <td>Pm </td> <td><a href="/wiki/Samarium(III)_acetylacetonate" title="Samarium(III) acetylacetonate">Sm(acac)<sub>3</sub></a> </td> <td><a href="/wiki/EuFOD" title="EuFOD">Eu(fod)<sub>3</sub></a><br /> <a href="/wiki/Europium_acetylacetonate" title="Europium acetylacetonate">Eu(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Gadolinium_acetylacetonate" title="Gadolinium acetylacetonate">Gd(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Terbium_acetylacetonate" title="Terbium acetylacetonate">Tb(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Dysprosium_acetylacetonate" title="Dysprosium acetylacetonate">Dy(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Holmium_acetylacetonate" title="Holmium acetylacetonate">Ho(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Erbium_acetylacetonate" title="Erbium acetylacetonate">Er(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Thulium_acetylacetonate" title="Thulium acetylacetonate">Tm(acac)<sub>3</sub></a> </td> <td><a href="/wiki/Ytterbium(III)_acetylacetonate" title="Ytterbium(III) acetylacetonate">Yb(acac)<sub>3</sub></a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td>Ac </td> <td>Th </td> <td>Pa </td> <td>U </td> <td>Np </td> <td>Pu </td> <td>Am </td> <td>Cm </td> <td>Bk </td> <td>Cf </td> <td>Es </td> <td>Fm </td> <td>Md </td> <td>No </td></tr></tbody></table></div> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Acetylacetone&oldid=1252829580">https://en.wikipedia.org/w/index.php?title=Acetylacetone&oldid=1252829580</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Diketones" title="Category:Diketones">Diketones</a></li><li><a href="/wiki/Category:Chelating_agents" title="Category:Chelating agents">Chelating agents</a></li><li><a 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