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class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Sodium ethoxide</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 24 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-24" 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">24 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%A5%D9%8A%D8%AB%D9%88%D9%83%D8%B3%D9%8A%D8%AF_%D8%A7%D9%84%D8%B5%D9%88%D8%AF%D9%8A%D9%88%D9%85" title="إيثوكسيد الصوديوم – Arabic" lang="ar" hreflang="ar" data-title="إيثوكسيد الصوديوم" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%D9%88%D8%AF%DB%8C%D9%88%D9%85_%D8%A7%D8%AA%D9%88%DA%A9%D8%B3%DB%8C%D8%AF" title="سودیوم اتوکسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="سودیوم اتوکسید" 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/Ethoxid_sodn%C3%BD" title="Ethoxid sodný – Czech" lang="cs" hreflang="cs" data-title="Ethoxid sodný" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Natriumethanolat" title="Natriumethanolat – German" lang="de" hreflang="de" data-title="Natriumethanolat" 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/Et%C3%B3xido_de_sodio" title="Etóxido de sodio – Spanish" lang="es" hreflang="es" data-title="Etóxido de sodio" 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/Natria_etoksido" title="Natria etoksido – Esperanto" lang="eo" hreflang="eo" data-title="Natria etoksido" 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%B3%D8%AF%DB%8C%D9%85_%D8%A7%D8%AA%D9%88%DA%A9%D8%B3%DB%8C%D8%AF" title="سدیم اتوکسید – Persian" lang="fa" hreflang="fa" data-title="سدیم اتوکسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89thanolate_de_sodium" title="Éthanolate de sodium – French" lang="fr" hreflang="fr" data-title="Éthanolate de sodium" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Natrium_etoksida" title="Natrium etoksida – Indonesian" lang="id" hreflang="id" data-title="Natrium etoksida" 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/Etossido_di_sodio" title="Etossido di sodio – Italian" lang="it" hreflang="it" data-title="Etossido di sodio" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9C%E1%83%90%E1%83%A2%E1%83%A0%E1%83%98%E1%83%A3%E1%83%9B%E1%83%98%E1%83%A1_%E1%83%94%E1%83%97%E1%83%9D%E1%83%A5%E1%83%A1%E1%83%98%E1%83%93%E1%83%98" title="ნატრიუმის ეთოქსიდი – Georgian" lang="ka" hreflang="ka" data-title="ნატრიუმის ეთოქსიდი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Natriumethoxide" title="Natriumethoxide – Dutch" lang="nl" hreflang="nl" data-title="Natriumethoxide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8A%E3%83%88%E3%83%AA%E3%82%A6%E3%83%A0%E3%82%A8%E3%83%88%E3%82%AD%E3%82%B7%E3%83%89" title="ナトリウムエトキシド – Japanese" lang="ja" hreflang="ja" data-title="ナトリウムエトキシド" 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/Etanolan_sodu" title="Etanolan sodu – Polish" lang="pl" hreflang="pl" data-title="Etanolan sodu" 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/Et%C3%B3xido_de_s%C3%B3dio" title="Etóxido de sódio – Portuguese" lang="pt" hreflang="pt" data-title="Etóxido de sódio" 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/Etoxid_de_sodiu" title="Etoxid de sodiu – Romanian" lang="ro" hreflang="ro" data-title="Etoxid de sodiu" 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%AD%D1%82%D0%B8%D0%BB%D0%B0%D1%82_%D0%BD%D0%B0%D1%82%D1%80%D0%B8%D1%8F" title="Этилат натрия – Russian" lang="ru" hreflang="ru" data-title="Этилат натрия" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Natrijum_etoksid" title="Natrijum etoksid – Serbian" lang="sr" hreflang="sr" data-title="Natrijum etoksid" 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/Natrijum_etoksid" title="Natrijum etoksid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Natrijum etoksid" 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/Natriumetoksidi" title="Natriumetoksidi – Finnish" lang="fi" hreflang="fi" data-title="Natriumetoksidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/Natriy_etilat%C4%B1" title="Natriy etilatı – Tatar" lang="tt" hreflang="tt" data-title="Natriy etilatı" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%82%D0%BE%D0%BA%D1%81%D0%B8%D0%B4_%D0%BD%D0%B0%D1%82%D1%80%D1%96%D1%8E" title="Етоксид натрію – Ukrainian" lang="uk" hreflang="uk" data-title="Етоксид натрію" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Natri_ethoxide" title="Natri ethoxide – Vietnamese" lang="vi" hreflang="vi" data-title="Natri ethoxide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Ionic compound made of a C2H5–O anion and a sodium cation</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>Sodium ethoxide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sodium_ethoxide.svg" class="mw-file-description" title="Ball-and-stick model of the sodium cation"><img alt="Ball-and-stick model of the sodium cation" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Sodium_ethoxide.svg/200px-Sodium_ethoxide.svg.png" decoding="async" width="200" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Sodium_ethoxide.svg/300px-Sodium_ethoxide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Sodium_ethoxide.svg/400px-Sodium_ethoxide.svg.png 2x" data-file-width="275" data-file-height="80" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png/220px-Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png/330px-Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png/440px-Sodium-ethoxide-xtal-layer-view-1-Mercury-3D-bs.png 2x" data-file-width="2000" data-file-height="2000" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Sodium ethanolate, sodium ethylate (<i>obsolete</i>)</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=141-52-6">141-52-6</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=%5BNa%2B%5D.%5BO-%5DCC">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>3593646 </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=52096">CHEBI:52096</a></span></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.8516.html">8516</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/100.004.989">100.004.989</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412779#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>205-487-5</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/2723922">2723922</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/1I9504387J">1I9504387J</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3027089">DTXSID3027089</a></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/C2H5O.Na/c1-2-3;/h2H2,1H3;/q-1;+1<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: QDRKDTQENPPHOJ-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/C2H5O.Na/c1-2-3;/h2H2,1H3;/q-1;+1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: QDRKDTQENPPHOJ-UHFFFAOYAQ</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%;">[Na+].[O-]CC</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><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>CH<sub class="template-chem2-sub">2</sub>ONa</span>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001680510000000000♠"></span>68.051</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.868 g/cm<sup>3</sup> (of a 21 wt% solution in ethanol) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>260 °C (500 °F; 533 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>Reacts </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td><a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Methanol" title="Methanol">methanol</a> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>15.5<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> <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-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-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> </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="H228: Flammable solid">H228</abbr>, <abbr class="abbr" title="H251: Self-heating: may catch fire">H251</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</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="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P235+P410: Keep cool. Protect from sunlight.">P235+P410</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="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</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="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</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="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</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="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</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="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P407: Maintain air gap between stacks or pallets.">P407</abbr>, <abbr class="abbr" title="P413: Store bulk masses greater than ... kg/... lbs at temperatures not exceeding ... °C/... °F.">P413</abbr>, <abbr class="abbr" title="P420: Store separately/away from other materials.">P420</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_3bf7c16f4e904b6c" /></span><map name="ImageMap_3bf7c16f4e904b6c"><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 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" title="Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid" title="Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid" /></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 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-white-text mw-no-invert"><a href="/wiki/NFPA_704#White" title="NFPA 704"><span class="nfpa-704-diamond-white-wors" title="Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid"><span class="nfpa-704-diamond-white-strike">W</span></span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://msds.chem.ox.ac.uk/SO/sodium_ethoxide.html">Oxford MSDS</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464401325&page2=Sodium+ethoxide">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>Sodium ethoxide,</b> also referred to as <b>sodium ethanolate</b>, is the <a href="/wiki/Ionic_compound" class="mw-redirect" title="Ionic compound">ionic</a>, <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula <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>ONa</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><sub class="template-chem2-sub">2</sub><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">5</sub><a href="/wiki/Oxygen" title="Oxygen">O</a><a href="/wiki/Sodium" title="Sodium">Na</a></span>, or NaOEt (Et = <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a>). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. It is commonly used as a strong <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <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=Sodium_ethoxide&action=edit&section=1" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Few procedures have been reported to prepare the anhydrous solid. Instead the material is typically prepared in a solution with ethanol. It is commercially available and as a solution in ethanol. It is easily prepared in the laboratory by treating <a href="/wiki/Sodium" title="Sodium">sodium</a> metal with absolute <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>:<sup id="cite_ref-OS_3-0" class="reference"><a href="#cite_note-OS-3"><span class="cite-bracket">[</span>3<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">2 CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH + 2 Na → 2 CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>ONa + <a href="/wiki/Hydrogen" title="Hydrogen">H<sub class="template-chem2-sub">2</sub></a></span></dd></dl> <p>The reaction of <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> with anhydrous ethanol suffers from incomplete conversion to the ethoxide, but can still produce dry NaOEt by precipitation using acetone,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> or by drying using additional NaOH.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_ethoxide&action=edit&section=2" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The crystal structure of sodium ethoxide has been determined by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>. It consists of layers of alternating <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sup class="template-chem2-sup">+</sup></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sup class="template-chem2-sup">−</sup></span> centres with disordered <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl groups</a> covering the top and bottom of each layer. The ethyl layers pack back-to-back resulting in a <a href="/wiki/Lamellar_structure" title="Lamellar structure">lamellar structure</a>. The reaction of sodium and ethanol sometimes forms other products such as the disolvate <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>ONa·2<a href="/wiki/Ethanol" title="Ethanol">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH</a></span>. Its crystal structure has been determined, although the structure of other phases in the <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>ONa/CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH</span> system remain unknown.<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> <table class="wikitable" style="text-align:center;"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png/200px-Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png" decoding="async" width="200" height="269" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png/300px-Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png/400px-Sodium-ethoxide-xtal-layer-stacking-Mercury-3D-bs.png 2x" data-file-width="1487" data-file-height="2000" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png/150px-Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png" decoding="async" width="150" height="177" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png/225px-Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png/300px-Sodium-ethoxide-xtal-Na-coordination-Mercury-3D-bs.png 2x" data-file-width="1691" data-file-height="2000" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png/150px-Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png" decoding="async" width="150" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png/225px-Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png/300px-Sodium-ethoxide-xtal-O-coordination-Mercury-3D-bs.png 2x" data-file-width="1851" data-file-height="2000" /></a></span> </td></tr> <tr> <td><small><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">ball-and-stick model</a> of layer stacking<br /> in the crystal structure of <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>ONa</span></small></td> <td><small><a href="/wiki/Coordination_geometry" title="Coordination geometry">coordination geometry</a> at Na</small></td> <td><small>coordination geometry at O</small> </td></tr></tbody></table> <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=Sodium_ethoxide&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium ethoxide is commonly used as a base in the <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a><sup id="cite_ref-Clayden-2012_7-0" class="reference"><a href="#cite_note-Clayden-2012-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Malonic_ester_synthesis" title="Malonic ester synthesis">malonic ester synthesis</a>.<sup id="cite_ref-Wang-2010_8-0" class="reference"><a href="#cite_note-Wang-2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Sodium ethoxide may either deprotonate the α-position of an <a href="/wiki/Ester" title="Ester">ester</a> molecule, forming an <a href="/wiki/Enolate" title="Enolate">enolate</a>, or the ester molecule may undergo a <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a> called <a href="/wiki/Transesterification" title="Transesterification">transesterification</a>. If the starting material is an ethyl ester, trans-esterification is irrelevant since the product is identical to the starting material. In practice, the alcohol/alkoxide solvating mixture must match the alkoxy components of the reacting esters to minimize the number of different products. </p><p>Many <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a> are prepared by <a href="/wiki/Salt_metathesis" class="mw-redirect" title="Salt metathesis">salt metathesis</a> from sodium ethoxide. </p> <div class="mw-heading mw-heading2"><h2 id="Stability">Stability</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_ethoxide&action=edit&section=4" title="Edit section: Stability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> Sodium ethoxide is prone to reaction with both water and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> in the <a href="/wiki/Air" class="mw-redirect" title="Air">air</a>.<sup id="cite_ref-Wethman_Derosa_Tran_Kang_p.2_9-0" class="reference"><a href="#cite_note-Wethman_Derosa_Tran_Kang_p.2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> This leads to degradation of stored samples over time, even in solid form. The physical appearance of degraded samples may not be obvious, but samples of sodium ethoxide gradually turn dark on storage. It has been reported that even newly-obtained commercial batches of sodium ethoxide show variable levels of degradation, and responsible as a major source of irreproducibility when used in <a href="/wiki/Suzuki_reaction" title="Suzuki reaction">Suzuki reactions</a>.<sup id="cite_ref-Wethman_Derosa_Tran_Kang_p.2_9-1" class="reference"><a href="#cite_note-Wethman_Derosa_Tran_Kang_p.2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></p><ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Sodium-ethoxide-reagent-bottle.jpg" class="mw-file-description" title="New bottle of sodium ethoxide from Sigma-Aldrich"><img alt="New bottle of sodium ethoxide from Sigma-Aldrich" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Sodium-ethoxide-reagent-bottle.jpg/120px-Sodium-ethoxide-reagent-bottle.jpg" decoding="async" width="120" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Sodium-ethoxide-reagent-bottle.jpg/180px-Sodium-ethoxide-reagent-bottle.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Sodium-ethoxide-reagent-bottle.jpg/240px-Sodium-ethoxide-reagent-bottle.jpg 2x" data-file-width="2048" data-file-height="1536" /></a></span></div> <div class="gallerytext">New bottle of sodium ethoxide from Sigma-Aldrich</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Sodium-ethoxide-reagent-contents.jpg" class="mw-file-description" title="Freshly opened container of sodium ethoxide showing discoloration caused by degradation when stored over oxygen and carbon dioxide."><img alt="Freshly opened container of sodium ethoxide showing discoloration caused by degradation when stored over oxygen and carbon dioxide." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Sodium-ethoxide-reagent-contents.jpg/120px-Sodium-ethoxide-reagent-contents.jpg" decoding="async" width="120" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Sodium-ethoxide-reagent-contents.jpg/180px-Sodium-ethoxide-reagent-contents.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Sodium-ethoxide-reagent-contents.jpg/240px-Sodium-ethoxide-reagent-contents.jpg 2x" data-file-width="1200" data-file-height="900" /></a></span></div> <div class="gallerytext">Freshly opened container of sodium ethoxide showing discoloration caused by degradation when stored over oxygen and carbon dioxide. </div> </li> </ul><p>In moist air, <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>ONa</span> <a href="/wiki/Hydrolyses" class="mw-redirect" title="Hydrolyses">hydrolyses</a> rapidly to <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> (NaOH). The conversion is not obvious and typical samples of <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>ONa</span> are contaminated with NaOH. </p><p>In <a href="/wiki/Moisture" title="Moisture">moisture</a>-free air, solid sodium ethoxide can form sodium ethyl carbonate from fixation of carbon dioxide from the air. Further reactions lead to degradation into a variety of other sodium <a href="/wiki/Salts" class="mw-redirect" title="Salts">salts</a> and <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>.<sup id="cite_ref-Wethman_Derosa_Tran_Kang_p.2_9-2" class="reference"><a href="#cite_note-Wethman_Derosa_Tran_Kang_p.2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>This instability can be prevented by storing sodium ethoxide under an <a href="/wiki/Inert_gas" title="Inert gas">inert atmosphere</a> (e.g., <a href="/wiki/Nitrogen" title="Nitrogen"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub></span></a>). </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_ethoxide&action=edit&section=5" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium ethoxide is a strong <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>, and is therefore corrosive. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_ethoxide&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkoxide" title="Alkoxide">Alkoxide</a></li> <li><a href="/wiki/Phenolate" class="mw-redirect" title="Phenolate">Phenolate</a></li> <li><a href="/wiki/Sodium_methoxide" title="Sodium methoxide">Sodium methoxide</a></li> <li><a href="/wiki/Sodium_phenoxide" title="Sodium phenoxide">Sodium phenoxide</a></li> <li><a href="/wiki/Potassium_methoxide" title="Potassium methoxide">Potassium methoxide</a></li> <li><a href="/wiki/Potassium_ethoxide" title="Potassium ethoxide">Potassium ethoxide</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_ethoxide&action=edit&section=7" 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"><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">disassociation constant of ethanol, referenced in the CRC Handbook of Chemistry and Physics 87th edition.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFK._Sinclair_WhitakerD._Todd_Whitaker2001" class="citation encyclopaedia cs1">K. Sinclair Whitaker; D. Todd Whitaker (2001). "Sodium Ethoxide". In Charette, André B. (ed.). <i>Encyclopedia of Reagents for Organic Synthesis</i>. <a href="/wiki/John_Wiley_%26_Sons" class="mw-redirect" title="John Wiley & Sons">John Wiley & Sons</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289X.rs070">10.1002/047084289X.rs070</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-84289-8" title="Special:BookSources/978-0-470-84289-8"><bdi>978-0-470-84289-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Sodium+Ethoxide&rft.btitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.pub=John+Wiley+%26+Sons&rft.date=2001&rft_id=info%3Adoi%2F10.1002%2F047084289X.rs070&rft.isbn=978-0-470-84289-8&rft.au=K.+Sinclair+Whitaker&rft.au=D.+Todd+Whitaker&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+ethoxide" class="Z3988"></span></span> </li> <li id="cite_note-OS-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-OS_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFC._S._Marvel,_E._E._Dreger1926" class="citation journal cs1">C. 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Beske; L. Tapmeyer; M. U. Schmidt (2020). "Crystal structure of sodium ethoxide (C<sub>2</sub>H<sub>5</sub>ONa), unravelled after 180 years". <i><a href="/wiki/Chemical_Communications" class="mw-redirect" title="Chemical Communications">Chem. Commun.</a></i> <b>56</b> (24): 3520–3523. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC9CC08907A">10.1039/C9CC08907A</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32101200">32101200</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:211523921">211523921</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Commun.&rft.atitle=Crystal+structure+of+sodium+ethoxide+%28C%3Csub%3E2%3C%2Fsub%3EH%3Csub%3E5%3C%2Fsub%3EONa%29%2C+unravelled+after+180+years&rft.volume=56&rft.issue=24&rft.pages=3520-3523&rft.date=2020&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A211523921%23id-name%3DS2CID&rft_id=info%3Apmid%2F32101200&rft_id=info%3Adoi%2F10.1039%2FC9CC08907A&rft.au=M.+Beske&rft.au=L.+Tapmeyer&rft.au=M.+U.+Schmidt&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+ethoxide" class="Z3988"></span></span> </li> <li id="cite_note-Clayden-2012-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Clayden-2012_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClaydenGreevesWarren2012" class="citation book cs1">Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). <i>Organic chemistry</i> (2nd ed.). 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John Wiley. pp. 1811–1815. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-70450-8" title="Special:BookSources/978-0-471-70450-8"><bdi>978-0-471-70450-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Comprehensive+organic+name+reactions+and+reagents&rft.pages=1811-1815&rft.pub=John+Wiley&rft.date=2010-09-15&rft.isbn=978-0-471-70450-8&rft.aulast=Wang&rft.aufirst=Zerong&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+ethoxide" class="Z3988"></span></span> </li> <li id="cite_note-Wethman_Derosa_Tran_Kang_p.2-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wethman_Derosa_Tran_Kang_p.2_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wethman_Derosa_Tran_Kang_p.2_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Wethman_Derosa_Tran_Kang_p.2_9-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWethmanDerosaTranKang2020" class="citation cs2">Wethman, Robert; Derosa, Joseph; Tran, Van; Kang, Taeho; Apolinar, Omar; Abraham, Anuji; Kleinmans, Roman; Wisniewski, Steven; Coombs, John; Engle, Keary (2020-08-19), <a rel="nofollow" class="external text" href="https://figshare.com/articles/preprint/An_Under-Appreciated_Source_of_Reproducibility_Issues_in_Cross-Coupling_Solid-State_Decomposition_of_Primary_Sodium_Alkoxides_in_Air/12818234"><i>An Under-Appreciated Source of Reproducibility Issues in Cross-Coupling: Solid-State Decomposition of Primary Sodium Alkoxides in Air</i></a>, American Chemical Society (ACS), <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.26434%2Fchemrxiv.12818234.v1">10.26434/chemrxiv.12818234.v1</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:242420220">242420220</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=An+Under-Appreciated+Source+of+Reproducibility+Issues+in+Cross-Coupling%3A+Solid-State+Decomposition+of+Primary+Sodium+Alkoxides+in+Air&rft.pub=American+Chemical+Society+%28ACS%29&rft.date=2020-08-19&rft_id=info%3Adoi%2F10.26434%2Fchemrxiv.12818234.v1&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A242420220%23id-name%3DS2CID&rft.aulast=Wethman&rft.aufirst=Robert&rft.au=Derosa%2C+Joseph&rft.au=Tran%2C+Van&rft.au=Kang%2C+Taeho&rft.au=Apolinar%2C+Omar&rft.au=Abraham%2C+Anuji&rft.au=Kleinmans%2C+Roman&rft.au=Wisniewski%2C+Steven&rft.au=Coombs%2C+John&rft.au=Engle%2C+Keary&rft_id=https%3A%2F%2Ffigshare.com%2Farticles%2Fpreprint%2FAn_Under-Appreciated_Source_of_Reproducibility_Issues_in_Cross-Coupling_Solid-State_Decomposition_of_Primary_Sodium_Alkoxides_in_Air%2F12818234&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+ethoxide" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; 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