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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 cyanoborohydride</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 20 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-20" 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">20 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%B3%D9%8A%D8%A7%D9%86%D9%88_%D8%A8%D9%88%D8%B1%D9%87%D9%8A%D8%AF%D8%B1%D9%8A%D8%AF_%D8%A7%D9%84%D8%B5%D9%88%D8%AF%D9%8A%D9%88%D9%85" title="سيانو بورهيدريد الصوديوم – Arabic" lang="ar" hreflang="ar" data-title="سيانو بورهيدريد 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%DB%8C%D8%A7%D9%86%D9%88%D8%A8%D9%88%D8%B1%D9%88%D9%87%DB%8C%D8%AF%D8%B1%DB%8C%D8%AF_%D8%B3%D9%88%D8%AF%DB%8C%D9%88%D9%85" title="سیانوبوروهیدرید سودیوم – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیانوبوروهیدرید سودیوم" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Natriumcyanoborhydrid" title="Natriumcyanoborhydrid – German" lang="de" hreflang="de" data-title="Natriumcyanoborhydrid" 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/Cianoborohidruro_de_sodio" title="Cianoborohidruro de sodio – Spanish" lang="es" hreflang="es" data-title="Cianoborohidruro 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_cianoborohidrido" title="Natria cianoborohidrido – Esperanto" lang="eo" hreflang="eo" data-title="Natria cianoborohidrido" 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%B3%DB%8C%D8%A7%D9%86%D9%88%D8%A8%D9%88%D8%B1%D9%88%D9%87%DB%8C%D8%AF%D8%B1%DB%8C%D8%AF" title="سدیم سیانوبوروهیدرید – Persian" lang="fa" hreflang="fa" data-title="سدیم سیانوبوروهیدرید" 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/Cyanoborohydrure_de_sodium" title="Cyanoborohydrure de sodium – French" lang="fr" hreflang="fr" data-title="Cyanoborohydrure 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Sodio_cianoboroidruro" title="Sodio cianoboroidruro – Italian" lang="it" hreflang="it" data-title="Sodio cianoboroidruro" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Natriumcyanoboorhydride" title="Natriumcyanoboorhydride – Dutch" lang="nl" hreflang="nl" data-title="Natriumcyanoboorhydride" 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%B7%E3%82%A2%E3%83%8E%E6%B0%B4%E7%B4%A0%E5%8C%96%E3%83%9B%E3%82%A6%E7%B4%A0%E3%83%8A%E3%83%88%E3%83%AA%E3%82%A6%E3%83%A0" title="シアノ水素化ホウ素ナトリウム – Japanese" lang="ja" hreflang="ja" data-title="シアノ水素化ホウ素ナトリウム" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Cianoborohidreto_de_s%C3%B3dio" title="Cianoborohidreto de sódio – Portuguese" lang="pt" hreflang="pt" data-title="Cianoborohidreto 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-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%BE%D0%B1%D0%BE%D1%80%D0%BE%D0%B3%D0%B8%D0%B4%D1%80%D0%B8%D0%B4_%D0%BD%D0%B0%D1%82%D1%80%D0%B8%D1%8F" title="Цианоборогидрид натрия – Russian" lang="ru" hreflang="ru" data-title="Цианоборогидрид натрия" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Natrijev_cianoborohidrid" title="Natrijev cianoborohidrid – Slovenian" lang="sl" hreflang="sl" data-title="Natrijev cianoborohidrid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Natrijum_cijanoborohidrid" title="Natrijum cijanoborohidrid – Serbian" lang="sr" hreflang="sr" data-title="Natrijum cijanoborohidrid" 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_cijanoborohidrid" title="Natrijum cijanoborohidrid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Natrijum cijanoborohidrid" 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/Natriumsyanoboorihydridi" title="Natriumsyanoboorihydridi – Finnish" lang="fi" hreflang="fi" data-title="Natriumsyanoboorihydridi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9A%E0%AF%8B%E0%AE%9F%E0%AE%BF%E0%AE%AF%E0%AE%AE%E0%AF%8D_%E0%AE%9A%E0%AE%AF%E0%AE%A9%E0%AF%8B%E0%AE%AA%E0%AF%8B%E0%AE%B0%E0%AF%8B_%E0%AE%90%E0%AE%A4%E0%AE%B0%E0%AF%88%E0%AE%9F%E0%AF%81" title="சோடியம் சயனோபோரோ ஐதரைடு – Tamil" lang="ta" hreflang="ta" data-title="சோடியம் சயனோபோரோ ஐதரைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sodyum_siyano_borhidr%C3%BCr" title="Sodyum siyano borhidrür – Turkish" lang="tr" hreflang="tr" data-title="Sodyum siyano borhidrür" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link 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dir="ltr"><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 cyanoborohydride </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sodium-cyanoborohydride-2D.png" class="mw-file-description" title="Line-bond structure of sodium cyanoborohydride"><img alt="Line-bond structure of sodium cyanoborohydride" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Sodium-cyanoborohydride-2D.png/220px-Sodium-cyanoborohydride-2D.png" decoding="async" width="220" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Sodium-cyanoborohydride-2D.png/330px-Sodium-cyanoborohydride-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Sodium-cyanoborohydride-2D.png/440px-Sodium-cyanoborohydride-2D.png 2x" data-file-width="1100" data-file-height="566" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Sodium cyanoboranuide</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;">Sodium cyanotrihydridoborate</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=25895-60-7">25895-60-7</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=%5BBH3-%5DC%23N.%5BNa%2B%5D">Interactive image</a></span></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/100.043.001">100.043.001</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q418193#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>247-317-2</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/5003444">5003444</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/C4I8C58P9T">C4I8C58P9T</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID40894864">DTXSID40894864</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q418193#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/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1</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%;">[BH3-]C#N.[Na+]</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">Na[BH<sub class="template-chem2-sub">3</sub>(CN)]</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="7001628400000000000♠"></span>62.84</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>white powder, <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.083 g/cm (25°C)<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>242 °C (468 °F; 515 K) decomposes </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>212 g/(100 mL) (29 °C) </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>soluble in water, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, <a href="/wiki/Diglyme" title="Diglyme">diglyme</a>, <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>, <a href="/wiki/Methanol" title="Methanol">methanol</a> <br /> slightly soluble in <a href="/wiki/Methanol" title="Methanol">methanol</a> <br /> insoluble in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Coordination_geometry" title="Coordination geometry">Coordination geometry</a></div> </td> <td>4 at boron atom </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td><a href="/wiki/Tetrahedral_molecular_geometry" title="Tetrahedral molecular geometry">Tetrahedral</a> at <a href="/wiki/Boron" title="Boron">boron</a> atom </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;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Flammable solid, fatal if swallowed, in contact with skin or if inhaled<br />Contact with acids liberates very toxic gas<br />Contact with water liberates highly flammable gas </td></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-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> </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="H300: Fatal if swallowed">H300</abbr>, <abbr class="abbr" title="H310: Fatal in contact with skin">H310</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H330: Fatal if inhaled">H330</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</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="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="P284: Wear respiratory protection.">P284</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_39d6574729123be9" /></span><map name="ImageMap_39d6574729123be9"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" title="Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" /><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 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</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 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</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 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus" class="notheme mw-no-invert">2</span></a></div></div></div></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Threshold_limit_value" title="Threshold limit value">Threshold limit value</a> (TLV)</div> </td> <td>5 mg/m3 (TWA) </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td>Sigma Aldrich<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;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Other <a href="/wiki/Ion" title="Ion">anions</a></div> </td> <td><a href="/wiki/Sodium_borohydride" title="Sodium borohydride">Sodium borohydride</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">Lithium aluminium hydride</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=438800960&page2=Sodium+cyanoborohydride">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 cyanoborohydride</b> is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Sodium" title="Sodium">Na</a>[<a href="/wiki/Boron" title="Boron">B</a><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">3</sub>(<a href="/wiki/Carbon" title="Carbon">C</a><a href="/wiki/Nitrogen" title="Nitrogen">N</a>)]</span>. It is a colourless salt used in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> for <a href="/wiki/Redox" title="Redox">chemical reduction</a> including that of <a href="/wiki/Imine" title="Imine">imines</a> and <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyls</a>. Sodium cyanoborohydride is a milder reductant than other conventional <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agents</a>.<sup id="cite_ref-Reitz-2002_2-0" class="reference"><a href="#cite_note-Reitz-2002-2"><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="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_cyanoborohydride&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium cyanoborohydride is a salt. The <a href="/wiki/Cationic" class="mw-redirect" title="Cationic">cationic</a> sodium ion, [Na]<sup>+</sup>, interacts with the <a href="/wiki/Ion" title="Ion">anionic</a> cyanoborohydride ion, [BH3(CN)]<sup>−</sup>. The anionic component of the salt is <a href="/wiki/Tetrahedral_molecular_geometry" title="Tetrahedral molecular geometry">tetrahedral</a> at the <a href="/wiki/Boron" title="Boron">boron</a> atom. </p><p>The <a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">electron-withdrawing</a> <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> substituent draws electron density away from the negatively charged boron; thus, reducing the electrophilic capabilities of the anionic component.<sup id="cite_ref-Reitz-2002_2-1" class="reference"><a href="#cite_note-Reitz-2002-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> This electronic phenomenon causes sodium cyanoborohydride to have more mild reducing qualities than other reducing agents. For example, Na[BH<sub>3</sub>(CN)] is less reducing than its counterpart <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a>, containing [BH<sub>4</sub>]<sup>−</sup>.<sup id="cite_ref-Reitz-2002_2-2" class="reference"><a href="#cite_note-Reitz-2002-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_cyanoborohydride&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium cyanoborohydride is a mild reducing agent. It is generally used for the reduction of <a href="/wiki/Imine" title="Imine">imines</a>. These reactions occur <pH 7 because the iminium ions are the actual substrates.<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> </p><p><a href="/wiki/Reductive_amination" title="Reductive amination">Reductive amination</a>, sometimes called the <i>Borch reaction</i>, is the conversion of a <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a> into an <a href="/wiki/Amine" title="Amine">amine</a> through an intermediate <a href="/wiki/Imine" title="Imine">imine</a>.<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> The carbonyl is first treated with ammonia to promote imine formation by nucleophilic attack. The imine is then reduced to an amine by sodium cyanoborohydride. This reaction works on both aldehydes and ketones. The carbonyl can be treated with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, a <a href="/wiki/Amine" title="Amine">primary amine</a>, or a secondary amine to produce, respectively, 1°, 2°, and 3° amines.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Aromatic_compound" title="Aromatic compound">Aromatic</a> <a href="/wiki/Ketone" title="Ketone">ketones</a> and aldehydes can be reductively <a href="/wiki/Deoxygenation" title="Deoxygenation">deoxygenated</a> using sodium cyanoborohydride.<sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This means that the carbonyl oxygen is being removed completely from the molecule. Deoxygenation using sodium cyanoborohydride is often done in the presence of <a href="/wiki/Trimethylsilyl_chloride" title="Trimethylsilyl chloride">trimethylsilyl chloride</a>, or TMSCl.<sup id="cite_ref-:0_6-1" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <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_cyanoborohydride&action=edit&section=3" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium cyanoborohydride can be purchased from most chemical suppliers. It can be synthesized by combining <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> and <a href="/wiki/Borane_tetrahydrofuran" class="mw-redirect" title="Borane tetrahydrofuran">borane tetrahydrofuran</a>.<sup id="cite_ref-:1_7-0" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<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">BH<sub class="template-chem2-sub">3</sub>·thf + NaCN → NaBH<sub class="template-chem2-sub">3</sub>CN + thf</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Selectivity">Selectivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_cyanoborohydride&action=edit&section=4" title="Edit section: Selectivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since sodium cyanoborohydride is a mild reducing agent, it gives good <a href="/wiki/Chemoselectivity" title="Chemoselectivity">chemoselectivity</a> for reaction with certain <a href="/wiki/Functional_group" title="Functional group">functional groups</a> in the presence of others. For example, sodium cyanoborohydride is generally incapable of reducing <a href="/wiki/Amide" title="Amide">amides</a>, <a href="/wiki/Ether" title="Ether">ethers</a>, <a href="/wiki/Ester" title="Ester">esters</a> and <a href="/wiki/Lactone" title="Lactone">lactones</a>, <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>, or <a href="/wiki/Epoxide" title="Epoxide">epoxides</a>.<sup id="cite_ref-:2_8-0" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Therefore, it can selectively reduce some functionalities in the presence of others. </p><p>Some examples of selective reduction include: </p> <ul><li>Reduction of <a href="/wiki/Iminium" title="Iminium">iminium</a> ions in the presence of <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyls</a><sup id="cite_ref-:2_8-1" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li> <li>Reduction of <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> in the presence of <a href="/wiki/Ketone" title="Ketone">ketones</a> and esters.<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></li> <li>Reduction of aldehydes in the presence of <a href="/wiki/Thioester" title="Thioester">thioesters</a><sup id="cite_ref-:2_8-2" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li></ul> <p>The selectivity of this reducing agent makes it an important tool in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. It allows for specific modifications to be made to complex organic molecules. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_cyanoborohydride&action=edit&section=5" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Georg_Wittig" title="Georg Wittig">Georg Wittig</a> was the first to synthesize a cyanoborohydride by treating <a href="/wiki/Lithium_borohydride" title="Lithium borohydride">lithium borohydride</a> with <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> in 1951.<sup id="cite_ref-:2_8-3" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The corresponding compound, sodium cyanoborohydride, was synthesized following a similar rationale by reacting <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a> with <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>.<sup id="cite_ref-:3_10-0" class="reference"><a href="#cite_note-:3-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The synthesis was later refined to use <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> and <a href="/wiki/Borane" title="Borane">borane</a> in <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">THF</a> making the process safer.<sup id="cite_ref-:3_10-1" class="reference"><a href="#cite_note-:3-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_cyanoborohydride&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/Sodium_triacetoxyborohydride" title="Sodium triacetoxyborohydride">Sodium triacetoxyborohydride</a> – a milder reductant, but unstable in water</li> <li><a href="/wiki/Sodium_borohydride" title="Sodium borohydride">Sodium borohydride</a> – a stronger, cheaper reductant</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_cyanoborohydride&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"><a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich Co.</a>, <a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/sial/42077">Sodium cyanoborohydride</a>. Retrieved on 2014-11-09.</span> </li> <li id="cite_note-Reitz-2002-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Reitz-2002_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Reitz-2002_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Reitz-2002_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBaxterReitz2002" class="citation journal cs1">Baxter, Ellen W.; Reitz, Allen B. 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(October 1980). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/ic50212a075">"Synthesis and properties of borohydride derivatives"</a>. <i>Inorganic Chemistry</i>. <b>19</b> (10): 3185–3186. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fic50212a075">10.1021/ic50212a075</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0020-1669">0020-1669</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inorganic+Chemistry&rft.atitle=Synthesis+and+properties+of+borohydride+derivatives&rft.volume=19&rft.issue=10&rft.pages=3185-3186&rft.date=1980-10&rft_id=info%3Adoi%2F10.1021%2Fic50212a075&rft.issn=0020-1669&rft.aulast=Hui&rft.aufirst=Benjamin+C.&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fic50212a075&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+cyanoborohydride" class="Z3988"></span></span> </li> <li id="cite_note-:2-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-:2_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:2_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:2_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:2_8-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLANE1975" class="citation journal cs1">LANE, Clinton F. (1975). <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1055/s-1975-23685">"Sodium Cyanoborohydride - A Highly Selective Reducing Agent for Organic Functional Groups"</a>. <i>Synthesis</i>. <b>1975</b> (3): 135–146. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-1975-23685">10.1055/s-1975-23685</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0039-7881">0039-7881</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:95157786">95157786</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synthesis&rft.atitle=Sodium+Cyanoborohydride+-+A+Highly+Selective+Reducing+Agent+for+Organic+Functional+Groups&rft.volume=1975&rft.issue=3&rft.pages=135-146&rft.date=1975&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A95157786%23id-name%3DS2CID&rft.issn=0039-7881&rft_id=info%3Adoi%2F10.1055%2Fs-1975-23685&rft.aulast=LANE&rft.aufirst=Clinton+F.&rft_id=http%3A%2F%2Fdx.doi.org%2F10.1055%2Fs-1975-23685&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+cyanoborohydride" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPaulShipmanOnabuleSproules2021" class="citation journal cs1">Paul, Avishek; Shipman, Michael A.; Onabule, Dolapo Y.; Sproules, Stephen; Symes, Mark D. (2021-04-15). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179549">"Selective aldehyde reductions in neutral water catalysed by encapsulation in a supramolecular cage"</a>. <i>Chemical Science</i>. <b>12</b> (14): 5082–5090. <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%2FD1SC00896J">10.1039/D1SC00896J</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2041-6539">2041-6539</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/PMC8179549">8179549</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/34163748">34163748</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Science&rft.atitle=Selective+aldehyde+reductions+in+neutral+water+catalysed+by+encapsulation+in+a+supramolecular+cage&rft.volume=12&rft.issue=14&rft.pages=5082-5090&rft.date=2021-04-15&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8179549%23id-name%3DPMC&rft.issn=2041-6539&rft_id=info%3Apmid%2F34163748&rft_id=info%3Adoi%2F10.1039%2FD1SC00896J&rft.aulast=Paul&rft.aufirst=Avishek&rft.au=Shipman%2C+Michael+A.&rft.au=Onabule%2C+Dolapo+Y.&rft.au=Sproules%2C+Stephen&rft.au=Symes%2C+Mark+D.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8179549&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+cyanoborohydride" class="Z3988"></span></span> </li> <li id="cite_note-:3-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-:3_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:3_10-1"><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="CITEREFAbdel-Magid1996" class="citation book cs1">Abdel-Magid, Ahmed F., ed. (1996-08-13). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/book/10.1021/bk-1996-0641"><i>Reductions in Organic Synthesis: Recent Advances and Practical Applications</i></a>. ACS Symposium Series. Vol. 641. Washington, DC: American Chemical Society. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fbk-1996-0641.ch001">10.1021/bk-1996-0641.ch001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8412-3381-2" title="Special:BookSources/978-0-8412-3381-2"><bdi>978-0-8412-3381-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Reductions+in+Organic+Synthesis%3A+Recent+Advances+and+Practical+Applications&rft.place=Washington%2C+DC&rft.series=ACS+Symposium+Series&rft.pub=American+Chemical+Society&rft.date=1996-08-13&rft_id=info%3Adoi%2F10.1021%2Fbk-1996-0641.ch001&rft.isbn=978-0-8412-3381-2&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fbook%2F10.1021%2Fbk-1996-0641&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+cyanoborohydride" 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abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Sodium_compounds" title="Template:Sodium compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Sodium_compounds" title="Template talk:Sodium compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Sodium_compounds" title="Special:EditPage/Template:Sodium compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Sodium_compounds" style="font-size:114%;margin:0 4em"><a href="/wiki/Sodium_compounds" title="Sodium compounds">Sodium compounds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Inorganic</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Halides</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_fluoride" title="Sodium fluoride">NaF</a></li> <li><a href="/wiki/Sodium_bifluoride" title="Sodium bifluoride">NaHF<sub>2</sub></a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">NaCl</a></li> <li><a href="/wiki/Sodium_bromide" title="Sodium bromide">NaBr</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">NaI</a></li> <li><a href="/wiki/Sodium_astatide" title="Sodium astatide">NaAt</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chalcogenides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_ozonide" title="Sodium ozonide">NaO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_superoxide" title="Sodium superoxide">NaO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_oxide" title="Sodium oxide">Na<sub>2</sub>O</a></li> <li><a href="/wiki/Sodium_peroxide" title="Sodium peroxide">Na<sub>2</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">NaOH</a></li> <li><a href="/wiki/Sodium_deuteroxide" title="Sodium deuteroxide">NaOD</a></li> <li><a href="/wiki/Sodium_sulfide" title="Sodium sulfide">Na<sub>2</sub>S</a></li> <li><a href="/wiki/Sodium_hydrosulfide" title="Sodium hydrosulfide">NaSH</a></li> <li><a href="/wiki/Sodium_selenide" title="Sodium selenide">Na<sub>2</sub>Se</a></li> <li><a href="/wiki/Sodium_hydroselenide" title="Sodium hydroselenide">NaSeH</a></li> <li><a href="/wiki/Sodium_telluride" title="Sodium telluride">Na<sub>2</sub>Te</a></li> <li><a href="/w/index.php?title=Sodium_hydrogen_telluride&action=edit&redlink=1" class="new" title="Sodium hydrogen telluride (page does not exist)">NaHTe</a></li> <li><a href="/wiki/Sodium_polonide" title="Sodium polonide">Na<sub>2</sub>Po</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pnictogenides</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_nitride" title="Sodium nitride">Na<sub>3</sub>N</a></li> <li><a href="/wiki/Sodium_azide" title="Sodium azide">NaN<sub>3</sub></a></li> <li><a href="/wiki/Sodium_amide" title="Sodium amide">NaNH<sub>2</sub></a></li> <li><a href="/wiki/Sodium_phosphide" title="Sodium phosphide">Na<sub>3</sub>P</a></li> <li><a href="/wiki/Sodium_arsenide" title="Sodium arsenide">Na<sub>3</sub>As</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxyhalides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_hypochlorite" title="Sodium hypochlorite">NaClO</a></li> <li><a href="/wiki/Sodium_chlorite" title="Sodium chlorite">NaClO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_chlorate" title="Sodium chlorate">NaClO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_perchlorate" title="Sodium perchlorate">NaClO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_hypobromite" title="Sodium hypobromite">NaBrO</a></li> <li><a href="/wiki/Sodium_bromite" title="Sodium bromite">NaBrO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_bromate" title="Sodium bromate">NaBrO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_perbromate" title="Sodium perbromate">NaBrO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_iodate" title="Sodium iodate">NaIO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_periodate" title="Sodium periodate">NaIO<sub>4</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxychalcogenides</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_sulfite" title="Sodium sulfite">Na<sub>2</sub>SO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_sulfate" title="Sodium sulfate">Na<sub>2</sub>SO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_bisulfite" title="Sodium bisulfite">NaHSO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_bisulfate" title="Sodium bisulfate">NaHSO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">Na<sub>2</sub>S<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Sodium_dithionite" title="Sodium dithionite">Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub></a></li> <li><a href="/wiki/Sodium_metabisulfite" title="Sodium metabisulfite">Na<sub>2</sub>S<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Sodium_dithionate" title="Sodium dithionate">Na<sub>2</sub>S<sub>2</sub>O<sub>6</sub></a></li> <li><a href="/wiki/Sodium_pyrosulfate" title="Sodium pyrosulfate">Na<sub>2</sub>S<sub>2</sub>O<sub>7</sub></a></li> <li><a href="/wiki/Sodium_persulfate" title="Sodium persulfate">Na<sub>2</sub>S<sub>2</sub>O<sub>8</sub></a></li> <li><a href="/wiki/Sodium_selenite" title="Sodium selenite">Na<sub>2</sub>SeO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_selenate" title="Sodium selenate">Na<sub>2</sub>SeO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_biselenite" class="mw-redirect" title="Sodium biselenite">NaHSeO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_tellurite" title="Sodium tellurite">Na<sub>2</sub>TeO<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxypnictogenides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_nitrite" title="Sodium nitrite">NaNO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_nitrate" title="Sodium nitrate">NaNO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_hyponitrite" title="Sodium hyponitrite">Na<sub>2</sub>N<sub>2</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Monosodium_phosphate" title="Monosodium phosphate">NaH<sub>2</sub>PO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_hypophosphite" title="Sodium hypophosphite">NaPO<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Disodium_hydrogen_phosphite" title="Disodium hydrogen phosphite">Na<sub>2</sub>HPO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_fluorophosphate" class="mw-redirect" title="Sodium fluorophosphate">Na<sub>2</sub>PO<sub>3</sub>F</a></li> <li><a href="/wiki/Sodium_dithiophosphate" title="Sodium dithiophosphate">Na<sub>3</sub>PS<sub>2</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Trisodium_phosphate" title="Trisodium phosphate">Na<sub>3</sub>PO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_triphosphate" title="Sodium triphosphate">Na<sub>5</sub>P<sub>3</sub>O<sub>10</sub></a></li> <li><a href="/wiki/Tetrasodium_pyrophosphate" title="Tetrasodium pyrophosphate">Na<sub>4</sub>P<sub>2</sub>O<sub>7</sub></a></li> <li><a href="/wiki/Disodium_pyrophosphate" title="Disodium pyrophosphate">Na<sub>2</sub>H<sub>2</sub>P<sub>2</sub>O<sub>7</sub></a></li> <li><a href="/wiki/Sodium_arsenite" title="Sodium arsenite">Na<sub>3</sub>AsO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_arsenate" title="Sodium arsenate">Na<sub>3</sub>AsO<sub>4</sub></a></li> <li><a href="/wiki/Disodium_hydrogen_arsenate" title="Disodium hydrogen arsenate">Na<sub>2</sub>HAsO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_dihydrogen_arsenate" title="Sodium dihydrogen arsenate">NaH<sub>2</sub>AsO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_antimonate" class="mw-redirect" title="Sodium antimonate">NaSbO<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_aluminium_hydride" title="Sodium aluminium hydride">NaAlH<sub>4</sub></a></li> <li><a href="/wiki/Sodium_aluminate" title="Sodium aluminate">NaAlO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_hexafluoroaluminate" title="Sodium hexafluoroaluminate">Na<sub>3</sub>AlF<sub>6</sub></a></li> <li><a href="/wiki/Sodium_alum" title="Sodium alum">NaAl(SO<sub>4</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Sodium_tetrachloroaurate" title="Sodium tetrachloroaurate">NaAuCl<sub>4</sub></a></li> <li><a href="/wiki/Sodium_hexafluoroantimonate" title="Sodium hexafluoroantimonate"><span class="chemf nowrap">NaSbF<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Sodium_hexafluoroarsenate" title="Sodium hexafluoroarsenate"><span class="chemf nowrap">NaAsF<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Sodium_hexafluorotitanate" title="Sodium hexafluorotitanate"><span class="chemf nowrap">Na<sub class="template-chem2-sub">2</sub>TiF<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Sodium_borohydride" title="Sodium borohydride">NaBH<sub>4</sub></a></li> <li><a class="mw-selflink selflink">NaBH<sub>3</sub>(CN)</a></li> <li><a href="/wiki/Sodium_metaborate" title="Sodium metaborate">NaBO<sub>2</sub></a></li> <li><a href="/wiki/Borax" title="Borax">Na<sub>2</sub>B<sub>4</sub>O<sub>7</sub></a></li> <li><a href="/wiki/Disodium_enneaborate" title="Disodium enneaborate">Na<sub>2</sub>B<sub>2</sub>O<sub>9</sub></a></li> <li><a href="/wiki/Disodium_octaborate" title="Disodium octaborate">Na<sub>2</sub>B<sub>8</sub>O<sub>13</sub></a></li> <li><a href="/wiki/Sodium_bismuthate" title="Sodium bismuthate">NaBiO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">NaCN</a></li> <li><a href="/w/index.php?title=Sodium_fulminate&action=edit&redlink=1" class="new" title="Sodium fulminate (page does not exist)">NaCNO</a></li> <li><a href="/wiki/Sodium_cobalt_oxide" title="Sodium cobalt oxide">NaCoO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_hydride" title="Sodium hydride">NaH</a></li> <li><a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">NaHCO<sub>3</sub></a></li> <li><a href="/w/index.php?title=Sodium_perxenate&action=edit&redlink=1" class="new" title="Sodium perxenate (page does not exist)">Na<sub>4</sub>XeO<sub>6</sub></a></li> <li><a href="/wiki/Monosodium_xenate" title="Monosodium xenate">NaHXeO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_permanganate" title="Sodium permanganate">NaMnO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_cyanate" title="Sodium cyanate">NaOCN</a></li> <li><a href="/wiki/Sodium_perrhenate" title="Sodium perrhenate">NaReO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_thiocyanate" title="Sodium thiocyanate">NaSCN</a></li> <li><a href="/wiki/Sodium_metatechnetate" class="mw-redirect" title="Sodium metatechnetate">NaTcO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_pertechnetate" title="Sodium pertechnetate">NaTcO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_metavanadate" title="Sodium metavanadate">NaVO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_carbonate" title="Sodium carbonate">Na<sub>2</sub>CO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_oxalate" title="Sodium oxalate">Na<sub>2</sub>C<sub>2</sub>O<sub>4</sub></a></li> <li><a href="/wiki/Sodium_1,3-dithiole-2-thione-4,5-dithiolate" title="Sodium 1,3-dithiole-2-thione-4,5-dithiolate">Na<sub>2</sub>C<sub>3</sub>S<sub>5</sub></a></li> <li><a href="/wiki/Sodium_chromate" title="Sodium chromate">Na<sub>2</sub>CrO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_dichromate" title="Sodium dichromate">Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub></a></li> <li><a href="/w/index.php?title=Sodium_trichromate&action=edit&redlink=1" class="new" title="Sodium trichromate (page does not exist)">Na<sub>2</sub>Cr<sub>3</sub>O<sub>10</sub></a></li> <li><a href="/wiki/Sodium_germanate" title="Sodium germanate">Na<sub>2</sub>GeO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_helide" class="mw-redirect" title="Sodium helide">Na<sub>2</sub>He</a></li> <li><a href="/wiki/Disodium_tetracarbonylferrate" title="Disodium tetracarbonylferrate">Na<sub>2</sub>[Fe(CO)<sub>4</sub>]</a></li> <li><a href="/wiki/Sodium_manganate" title="Sodium manganate">Na<sub>2</sub>MnO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_molybdate" title="Sodium molybdate">Na<sub>2</sub>MoO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_hexachloroiridate(III)" title="Sodium hexachloroiridate(III)">Na<sub>3</sub>IrCl<sub>6</sub></a></li> <li><a href="/wiki/Sodium_hexachloroplatinate" title="Sodium hexachloroplatinate">Na<sub>2</sub>PtCl<sub>6</sub></a></li> <li><a href="/wiki/Sodium_uranate" class="mw-redirect" title="Sodium uranate">Na<sub>2</sub>O(UO<sub>3</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Sodium_tetrathionate" title="Sodium tetrathionate">Na<sub>2</sub>S<sub>4</sub>O<sub>6</sub></a></li> <li><a href="/wiki/Sodium_silicate" title="Sodium silicate">Na<sub>2</sub>SiO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_metatitanate" title="Sodium metatitanate">Na<sub>2</sub>TiO<sub>3</sub></a></li> <li><a href="/wiki/Sodium_diuranate" title="Sodium diuranate">Na<sub>2</sub>U<sub>2</sub>O<sub>7</sub></a></li> <li><a href="/wiki/Sodium_tungstate" title="Sodium tungstate">Na<sub>2</sub>WO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_zincate" title="Sodium zincate">Na<sub>2</sub>Zn(OH)<sub>4</sub></a></li> <li><a href="/wiki/Sodium_orthovanadate" title="Sodium orthovanadate">Na<sub>3</sub>VO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_decavanadate" title="Sodium decavanadate">Na<sub>6</sub>V<sub>10</sub>O<sub>28</sub></a></li> <li><a href="/wiki/Sodium_ferrocyanide" title="Sodium ferrocyanide">Na<sub>4</sub>Fe(CN)<sub>6</sub></a></li> <li><a href="/w/index.php?title=Sodium_ferricyanide&action=edit&redlink=1" class="new" title="Sodium ferricyanide (page does not exist)">Na<sub>3</sub>Fe(CN)<sub>6</sub></a></li> <li><a href="/wiki/Sodium_ferrioxalate" title="Sodium ferrioxalate">Na<sub>3</sub>Fe(C<sub>2</sub>O<sub>4</sub>)<sub>3</sub></a></li> <li><a href="/wiki/Sodium_orthosilicate" title="Sodium orthosilicate">Na<sub>4</sub>SiO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_fluorosilicate" title="Sodium fluorosilicate">Na<sub>2</sub>SiF<sub>6</sub></a></li> <li><a href="/wiki/Sodium_hexanitritocobaltate(III)" title="Sodium hexanitritocobaltate(III)">Na<sub>3</sub>[Co(NO<sub>2</sub>)<sub>6</sub>]</a></li> <li><a href="/wiki/Sodium_bis(trimethylsilyl)amide" title="Sodium bis(trimethylsilyl)amide">NaNSi<sub>2</sub>(CH<sub>3</sub>)<sub>6</sub></a></li> <li><a href="/wiki/Sodium_tetrachloropalladate" title="Sodium tetrachloropalladate">Na<sub>2</sub>PdCl<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organosodium" class="mw-redirect" title="Organosodium">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sodium_methoxide" title="Sodium methoxide">CH<sub>3</sub>ONa</a></li> <li><a href="/wiki/Sodium_ethoxide" title="Sodium ethoxide">C<sub>2</sub>H<sub>5</sub>ONa</a></li> <li><a href="/wiki/Sodium_formate" title="Sodium formate">HCOONa</a></li> <li><a href="/wiki/Sodium_propionate" title="Sodium propionate">C<sub>2</sub>H<sub>5</sub>COONa</a></li> <li><a href="/wiki/Sodium_butyrate" title="Sodium butyrate">C<sub>3</sub>H<sub>7</sub>COONa</a></li> <li><a href="/wiki/Sodium_tartrate" title="Sodium tartrate">Na<sub>2</sub>C<sub>4</sub>H<sub>4</sub>O<sub>6</sub></a></li> <li><a href="/wiki/Sodium_bitartrate" class="mw-redirect" title="Sodium bitartrate">C<sub>4</sub>H<sub>5</sub>NaO<sub>6</sub></a></li> <li><a href="/wiki/Sodium_acetate" title="Sodium acetate">NaCH<sub>3</sub>COO</a></li> <li><a href="/wiki/Sodium_benzoate" title="Sodium benzoate">NaC<sub>6</sub>H<sub>5</sub>CO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">NaC<sub>6</sub>H<sub>4</sub>(OH)CO<sub>2</sub></a></li> <li><a href="/wiki/Sodium_laurate" title="Sodium laurate">NaC<sub>12</sub>H<sub>23</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Sodium_naphthalene" title="Sodium naphthalene">NaC<sub>10</sub>H<sub>8</sub></a></li> <li><a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">Na<sub>2</sub>[Fe[CN<sub>5</sub>]NO]</a></li> <li><a href="/wiki/Sodium_bis(2-methoxyethoxy)aluminium_hydride" title="Sodium bis(2-methoxyethoxy)aluminium hydride">C<sub>6</sub>H<sub>16</sub>AlNaO<sub>4</sub></a></li> <li><a href="/wiki/Sodium_erythorbate" title="Sodium erythorbate">NaC<sub>6</sub>H<sub>7</sub>O<sub>6</sub></a></li> <li><a href="/wiki/Monosodium_Glutamate" class="mw-redirect" title="Monosodium Glutamate">C<sub>5</sub>H<sub>8</sub>NO<sub>4</sub>Na</a></li> <li><a href="/wiki/Phenylsodium" title="Phenylsodium">C<sub>6</sub>H<sub>5</sub>Na</a></li> <li><a href="/wiki/N-Butylsodium" title="N-Butylsodium">C<sub>4</sub>H<sub>9</sub>Na</a></li> <li><a href="/wiki/Sodium_cyclopentadienide" title="Sodium cyclopentadienide">NaC<sub>5</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Sodium_Palmitate&action=edit&redlink=1" class="new" title="Sodium Palmitate (page does not exist)">C<sub>15</sub>H<sub>31</sub>COONa</a></li> <li><a href="/w/index.php?title=Sodium_Oleate&action=edit&redlink=1" class="new" title="Sodium Oleate (page does not exist)">C<sub>17</sub>H<sub>33</sub>COONa</a></li> <li><a href="/wiki/Sodium_stearate" title="Sodium stearate">C<sub>18</sub>H<sub>35</sub>O<sub>2</sub>Na</a></li> <li><a href="/wiki/Maitotoxin" title="Maitotoxin">C<sub>164</sub>H<sub>256</sub>O<sub>68</sub>S<sub>2</sub>Na<sub>2</sub></a></li></ul> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1012311289">.mw-parser-output .asbox{position:relative;overflow:hidden}.mw-parser-output .asbox table{background:transparent}.mw-parser-output .asbox p{margin:0}.mw-parser-output .asbox p+p{margin-top:0.25em}.mw-parser-output .asbox-body{font-style:italic}.mw-parser-output .asbox-note{font-size:smaller}.mw-parser-output .asbox .navbar{position:absolute;top:-0.75em;right:1em;display:none}</style><div role="note" class="metadata plainlinks asbox stub"><table role="presentation"><tbody><tr class="noresize"><td><span typeof="mw:File"><a href="/wiki/File:Nuvola_apps_edu_science.svg" class="mw-file-description"><img alt="Stub icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/35px-Nuvola_apps_edu_science.svg.png" decoding="async" width="35" 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