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class="vector-toc-link" href="#Coordination_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Coordination chemistry</span> </div> </a> <ul id="toc-Coordination_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Protonolysis_and_hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protonolysis_and_hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Protonolysis and hydrolysis</span> </div> </a> <ul id="toc-Protonolysis_and_hydrolysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Paper_manufacture" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Paper_manufacture"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Paper manufacture</span> </div> </a> <ul id="toc-Paper_manufacture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Chemical synthesis</span> </div> </a> <ul id="toc-Chemical_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Niche_or_abandoned_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_or_abandoned_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Niche or abandoned applications</span> </div> </a> <ul id="toc-Niche_or_abandoned_applications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button 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 borohydride</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 30 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-30" 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">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Natriumboorhidried" title="Natriumboorhidried – Afrikaans" lang="af" hreflang="af" data-title="Natriumboorhidried" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%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="بورهيدريد الصوديوم – Arabic" lang="ar" hreflang="ar" data-title="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%D9%88%D8%AF%DB%8C%D9%88%D9%85_%D8%AA%D8%AA%D8%B1%D8%A7_%D9%87%DB%8C%D8%AF%D8%B1%D9%88%D8%A8%D9%88%D8%B1%D8%A7%D8%AA" title="سودیوم تترا هیدروبورات – South Azerbaijani" lang="azb" hreflang="azb" data-title="سودیوم تترا هیدروبورات" 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/Tetrahydridoboritan_sodn%C3%BD" title="Tetrahydridoboritan sodný – Czech" lang="cs" hreflang="cs" data-title="Tetrahydridoboritan sodný" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Natriumborhydrid" title="Natriumborhydrid – Danish" lang="da" hreflang="da" data-title="Natriumborhydrid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Natriumborhydrid" title="Natriumborhydrid – German" lang="de" hreflang="de" data-title="Natriumborhydrid" 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/Borohidruro_de_sodio" title="Borohidruro de sodio – Spanish" lang="es" hreflang="es" data-title="Borohidruro 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_borohidrido" title="Natria borohidrido – Esperanto" lang="eo" hreflang="eo" data-title="Natria borohidrido" 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%AA%D8%AA%D8%B1%D8%A7_%D9%87%DB%8C%D8%AF%D8%B1%D9%88%D8%A8%D9%88%D8%B1%D8%A7%D8%AA" title="سدیم تترا هیدروبورات – Persian" lang="fa" hreflang="fa" data-title="سدیم تترا هیدروبورات" 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/T%C3%A9trahydruroborate_de_sodium" title="Tétrahydruroborate de sodium – French" lang="fr" hreflang="fr" data-title="Tétrahydruroborate 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-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%88%98%EC%86%8C%ED%99%94_%EB%B6%95%EC%86%8C_%EB%82%98%ED%8A%B8%EB%A5%A8" title="수소화 붕소 나트륨 – Korean" lang="ko" hreflang="ko" data-title="수소화 붕소 나트륨" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%86%D5%A1%D5%BF%D6%80%D5%AB%D5%B8%D6%82%D5%B4%D5%AB_%D5%A2%D5%B8%D6%80%D5%B0%D5%AB%D5%A4%D6%80%D5%AB%D5%A4" title="Նատրիումի բորհիդրիդ – Armenian" lang="hy" hreflang="hy" data-title="Նատրիումի բորհիդրիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A5%8B%E0%A4%A1%E0%A4%BF%E0%A4%AF%E0%A4%AE_%E0%A4%AC%E0%A5%8B%E0%A4%B0%E0%A5%8B%E0%A4%B9%E0%A4%BE%E0%A4%87%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A4%BE%E0%A4%87%E0%A4%A1" title="सोडियम बोरोहाइड्राइड – Hindi" lang="hi" hreflang="hi" data-title="सोडियम बोरोहाइड्राइड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Natrium_borohidrida" title="Natrium borohidrida – Indonesian" lang="id" hreflang="id" data-title="Natrium borohidrida" 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/Boroidruro_di_sodio" title="Boroidruro di sodio – Italian" lang="it" hreflang="it" data-title="Boroidruro 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-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Natriumboorhydride" title="Natriumboorhydride – Dutch" lang="nl" hreflang="nl" data-title="Natriumboorhydride" 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/%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="水素化ホウ素ナトリウム – Japanese" lang="ja" hreflang="ja" data-title="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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Borowodorek_sodu" title="Borowodorek sodu – Polish" lang="pl" hreflang="pl" data-title="Borowodorek 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/Borohidreto_de_s%C3%B3dio" title="Borohidreto de sódio – Portuguese" lang="pt" hreflang="pt" data-title="Borohidreto 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/Borohidrur%C4%83_de_sodiu" title="Borohidrură de sodiu – Romanian" lang="ro" hreflang="ro" data-title="Borohidrură 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%91%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="Борогидрид натрия – Russian" lang="ru" hreflang="ru" data-title="Борогидрид натрия" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tetrahydridoboritan_sodn%C3%BD" title="Tetrahydridoboritan sodný – Slovak" lang="sk" hreflang="sk" data-title="Tetrahydridoboritan sodný" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Natrijum_borohidrid" title="Natrijum borohidrid – Serbian" lang="sr" hreflang="sr" data-title="Natrijum borohidrid" 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_borohidrid" title="Natrijum borohidrid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Natrijum borohidrid" 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/Natriumboorihydridi" title="Natriumboorihydridi – Finnish" lang="fi" hreflang="fi" data-title="Natriumboorihydridi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Natriumborhydrid" title="Natriumborhydrid – Swedish" lang="sv" hreflang="sv" data-title="Natriumborhydrid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sodyum_borhidr%C3%BCr" title="Sodyum borhidrür – Turkish" lang="tr" hreflang="tr" data-title="Sodyum borhidrür" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%91%D0%BE%D1%80%D0%BE%D0%B3%D1%96%D0%B4%D1%80%D0%B8%D0%B4_%D0%BD%D0%B0%D1%82%D1%80%D1%96%D1%8E" title="Борогідрид натрію – Ukrainian" lang="uk" hreflang="uk" data-title="Борогідрид 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_borohydride" title="Natri borohydride – Vietnamese" lang="vi" hreflang="vi" data-title="Natri borohydride" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A1%BC%E6%B0%A2%E5%8C%96%E9%92%A0" title="硼氢化钠 – Chinese" lang="zh" hreflang="zh" data-title="硼氢化钠" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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<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">Chemical compound</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 borohydride </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sodium_borohydride.svg" class="mw-file-description" title="Wireframe model of sodium borohydride"><img alt="Wireframe model of sodium borohydride" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Sodium_borohydride.svg/220px-Sodium_borohydride.svg.png" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Sodium_borohydride.svg/330px-Sodium_borohydride.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Sodium_borohydride.svg/440px-Sodium_borohydride.svg.png 2x" data-file-width="170" data-file-height="100" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sodium_borohydride.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Sodium_borohydride.jpg/220px-Sodium_borohydride.jpg" decoding="async" width="220" height="308" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Sodium_borohydride.jpg/330px-Sodium_borohydride.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Sodium_borohydride.jpg/440px-Sodium_borohydride.jpg 2x" data-file-width="500" data-file-height="700" /></a></span> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Sodium-3D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Sodium-3D.png/110px-Sodium-3D.png" decoding="async" width="110" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Sodium-3D.png/165px-Sodium-3D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Sodium-3D.png/220px-Sodium-3D.png 2x" data-file-width="900" data-file-height="900" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Borohydride-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Borohydride-3D-vdW.png/110px-Borohydride-3D-vdW.png" decoding="async" width="110" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Borohydride-3D-vdW.png/165px-Borohydride-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Borohydride-3D-vdW.png/220px-Borohydride-3D-vdW.png 2x" data-file-width="534" data-file-height="539" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Sodium tetrahydridoborate(1–)</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Sodium boranuide</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=16940-66-2">16940-66-2</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=15681-89-7">15681-89-7</a></span> (<sup>2</sup><i>D</i><sub>4</sub>)<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.%5BBH4-%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=50985">CHEBI:50985</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.26189.html">26189</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><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.9052313.html">9052313</a></span> (<sup>2</sup><i>D</i><sub>4</sub>)<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><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.9312193.html">9312193</a></span> (<sup>3</sup><i>T</i><sub>4</sub>)<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/100.037.262">100.037.262</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407895#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>241-004-4</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>23167 </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Sodium+borohydride">Sodium+borohydride</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4311764">4311764</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/23673181">23673181</a></span> (<sup>2</sup><i>D</i><sub>4</sub>)</li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/23671303">23671303</a></span> (<sup>3</sup><i>T</i><sub>4</sub>)</li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>ED3325000</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/87L0B9CPPA">87L0B9CPPA</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1426 </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/DTXSID80893977">DTXSID80893977</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407895#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/BH4.Na/h1H4;/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: YOQDYZUWIQVZSF-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/BH4.Na/h1H4;/q-1;+1</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%;">Key: YOQDYZUWIQVZSF-UHFFF</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+].[BH4-]</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">4</sub>]</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="7001378300000000000♠"></span>37.83</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>white crystals <br /> <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>1.07 g/cm<sup>3</sup><sup id="cite_ref-crc_1-0" class="reference"><a href="#cite_note-crc-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>400 °C (752 °F; 673 K)(decomposes)<sup id="cite_ref-crc_1-2" class="reference"><a href="#cite_note-crc-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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>550 g/L<sup id="cite_ref-crc_1-1" class="reference"><a href="#cite_note-crc-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>soluble in liquid <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, <a href="/wiki/Amine" title="Amine">amines</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure<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> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td>Cubic (NaCl), <a href="/wiki/Pearson_symbol" title="Pearson symbol">cF8 </a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Space_group" title="Space group">Space group</a></div> </td> <td>Fm<span style="text-decoration:overline;">3</span>m, No. 225 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Lattice_constant" title="Lattice constant">Lattice constant</a></div> </td> <td><div><i>a</i> = 0.6157 nm</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry<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> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>86.8 J·mol<sup>−1</sup>·K<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>101.3 J·mol<sup>−1</sup>·K<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−188.6 kJ·mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gibbs_free_energy#Standard_energy_change_of_formation" title="Gibbs free energy">Gibbs free energy</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>G</i><sup>⦵</sup>)</span></div> </td> <td>−123.9 kJ·mol<sup>−1</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>:<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> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><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> </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="H260: In contact with water releases flammable gases which may ignite spontaneously">H260</abbr>, <abbr class="abbr" title="H301: Toxic if swallowed">H301</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H360F: May damage fertility">H360F</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P231+P232: Handle and store contents under inert gas. Protect from moisture">P231+P232</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P308+P313: IF exposed or concerned: Get medical advice/attention.">P308+P313</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P402+P404: Store in a dry place. Store in a closed container.">P402+P404</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_f3d65a458d6e6bae" /></span><map name="ImageMap_f3d65a458d6e6bae"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><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 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 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</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 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/Flash_point" title="Flash point">Flash point</a> </td> <td>70 °C (158 °F; 343 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>ca. 220 °C (428 °F; 493 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>3% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>160 mg/kg (Oral – Rat)<br />230 mg/kg (Dermal – Rabbit) </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_cyanoborohydride" title="Sodium cyanoborohydride">Sodium cyanoborohydride</a><br /><a href="/wiki/Sodium_hydride" title="Sodium hydride">Sodium hydride</a><br /><a href="/wiki/Sodium_borate" title="Sodium borate">Sodium borate</a><br /><a href="/wiki/Borax" title="Borax">Borax</a><br /><a href="/wiki/Sodium_aluminum_hydride" class="mw-redirect" title="Sodium aluminum hydride">Sodium aluminum hydride</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Other <a href="/wiki/Ion" title="Ion">cations</a></div> </td> <td><a href="/wiki/Lithium_borohydride" title="Lithium borohydride">Lithium 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><br /> <a href="/wiki/Sodium_triacetoxyborohydride" title="Sodium triacetoxyborohydride">Sodium triacetoxyborohydride</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="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464400313&page2=Sodium+borohydride">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 borohydride</b>, also known as <b>sodium tetrahydridoborate</b> and <b>sodium tetrahydroborate</b>,<sup id="cite_ref-google_5-0" class="reference"><a href="#cite_note-google-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> is an <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <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">4</sub></span> (sometimes written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na[BH<sub class="template-chem2-sub">4</sub>]</span>). It is a white <a href="/wiki/Crystalline" class="mw-redirect" title="Crystalline">crystalline</a> solid, usually encountered as an aqueous <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic solution</a>. Sodium borohydride is a <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agent</a> that finds application in <a href="/wiki/Papermaking" title="Papermaking">papermaking</a> and dye industries. It is also used as a reagent in organic synthesis.<sup id="cite_ref-eros_6-0" class="reference"><a href="#cite_note-eros-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The compound was discovered in the 1940s by <a href="/wiki/Hermann_Irving_Schlesinger" title="Hermann Irving Schlesinger">H. I. Schlesinger</a>, who led a team seeking volatile uranium compounds.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-sch1945_8-0" class="reference"><a href="#cite_note-sch1945-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Results of this wartime research were declassified and published in 1953. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The compound is soluble in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>, certain <a href="/wiki/Ether" title="Ether">ethers</a>, and water, although it slowly hydrolyzes.<sup id="cite_ref-eEROS_9-0" class="reference"><a href="#cite_note-eEROS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable floatleft"> <tbody><tr> <th>Solvent</th> <th>Solubility (g/(100 mL))<sup id="cite_ref-eEROS_9-1" class="reference"><a href="#cite_note-eEROS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><a href="/wiki/Methanol" title="Methanol"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OH</span></a></td> <td>13 </td></tr> <tr> <td><a href="/wiki/Ethanol" title="Ethanol"><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>OH</span></a></td> <td>3.16 </td></tr> <tr> <td><a href="/wiki/Diglyme" title="Diglyme">Diglyme</a></td> <td>5.15 </td></tr> <tr> <td><a href="/wiki/Diethyl_ether" title="Diethyl ether"><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>)<sub class="template-chem2-sub">2</sub>O</span></a></td> <td>insoluble </td></tr></tbody></table> <p>Sodium borohydride is an odorless white to gray-white <a href="/wiki/Microcrystalline" title="Microcrystalline">microcrystalline</a> powder that often forms lumps. It can be purified by recrystallization from warm (50 °C) <a href="/wiki/Diglyme" title="Diglyme">diglyme</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Sodium borohydride is soluble in <a href="/wiki/Protic_solvents" class="mw-redirect" title="Protic solvents">protic solvents</a> such as water and lower alcohols. It also reacts with these <a href="/wiki/Protic_solvent" title="Protic solvent">protic solvents</a> to produce <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub></span>; however, these reactions are fairly slow. Complete decomposition of a methanol solution requires nearly 90 min at 20 °C.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It decomposes in neutral or acidic aqueous solutions, but is stable at pH 14.<sup id="cite_ref-eEROS_9-2" class="reference"><a href="#cite_note-eEROS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structure">Structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=2" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> is a salt, consisting of the tetrahedral <a href="/wiki/Borohydride" title="Borohydride"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[BH<sub class="template-chem2-sub">4</sub>]<sup class="template-chem2-sup">−</sup></span></a> anion. The solid is known to exist as three <a href="/wiki/Polymorphism_(materials_science)" class="mw-redirect" title="Polymorphism (materials science)">polymorphs</a>: <i>α</i>, <i>β</i> and <i>γ</i>. The stable phase at room temperature and pressure is <i>α</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span>, which is cubic and adopts an <a href="/wiki/Halite_structure" class="mw-redirect" title="Halite structure">NaCl</a>-type structure, in the <i>Fm<span style="text-decoration:overline;">3</span>m</i> <a href="/wiki/Space_group" title="Space group">space group</a>. At a pressure of 6.3 GPa, the structure changes to the tetragonal <i>β</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> (space group <i>P42<sub>1</sub>c</i>) and at 8.9 GPa, the orthorhombic <i>γ</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> (space group <i>Pnma</i>) becomes the most stable.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-packed"> <li class="gallerybox" style="width: 162px"> <div class="thumb" style="width: 160px;"><span typeof="mw:File"><a href="/wiki/File:Alpha-sodium-borohydride-xtal-2007-3D-balls.png" class="mw-file-description" title="α-NaBH4"><img alt="α-NaBH4" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Alpha-sodium-borohydride-xtal-2007-3D-balls.png/240px-Alpha-sodium-borohydride-xtal-2007-3D-balls.png" decoding="async" width="160" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Alpha-sodium-borohydride-xtal-2007-3D-balls.png/359px-Alpha-sodium-borohydride-xtal-2007-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Alpha-sodium-borohydride-xtal-2007-3D-balls.png/479px-Alpha-sodium-borohydride-xtal-2007-3D-balls.png 2x" data-file-width="1098" data-file-height="1100" /></a></span></div> <div class="gallerytext"><i>α</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span></div> </li> <li class="gallerybox" style="width: 194.66666666667px"> <div class="thumb" style="width: 192.66666666667px;"><span typeof="mw:File"><a href="/wiki/File:Beta-sodium-borohydride-xtal-2007-3D-balls.png" class="mw-file-description" title="β-NaBH4"><img alt="β-NaBH4" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Beta-sodium-borohydride-xtal-2007-3D-balls.png/289px-Beta-sodium-borohydride-xtal-2007-3D-balls.png" decoding="async" width="193" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/Beta-sodium-borohydride-xtal-2007-3D-balls.png/433px-Beta-sodium-borohydride-xtal-2007-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/Beta-sodium-borohydride-xtal-2007-3D-balls.png/577px-Beta-sodium-borohydride-xtal-2007-3D-balls.png 2x" data-file-width="1100" data-file-height="915" /></a></span></div> <div class="gallerytext"><i>β</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span></div> </li> <li class="gallerybox" style="width: 165.33333333333px"> <div class="thumb" style="width: 163.33333333333px;"><span typeof="mw:File"><a href="/wiki/File:Gamma-sodium-borohydride-xtal-2007-3D-balls.png" class="mw-file-description" title="γ-NaBH4"><img alt="γ-NaBH4" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Gamma-sodium-borohydride-xtal-2007-3D-balls.png/245px-Gamma-sodium-borohydride-xtal-2007-3D-balls.png" decoding="async" width="164" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Gamma-sodium-borohydride-xtal-2007-3D-balls.png/368px-Gamma-sodium-borohydride-xtal-2007-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Gamma-sodium-borohydride-xtal-2007-3D-balls.png/490px-Gamma-sodium-borohydride-xtal-2007-3D-balls.png 2x" data-file-width="1100" data-file-height="1077" /></a></span></div> <div class="gallerytext"><i>γ</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Synthesis_and_handling">Synthesis and handling</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=3" title="Edit section: Synthesis and handling"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For commercial <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> production, the Brown-Schlesinger process and the Bayer process are the most popular methods. In the Brown-Schlesinger process sodium borohydride is industrially prepared from <a href="/wiki/Sodium_hydride" title="Sodium hydride">sodium hydride</a> (produced by reacting Na and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub></span>) and <a href="/wiki/Trimethyl_borate" title="Trimethyl borate">trimethyl borate</a> at 250–270 °C: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">B(OCH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub> + 4 NaH → NaBH<sub class="template-chem2-sub">4</sub> + 3 NaOCH<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>Millions of kilograms are produced annually, far exceeding the production levels of any other hydride reducing agent.<sup id="cite_ref-Ullmann_15-0" class="reference"><a href="#cite_note-Ullmann-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> In the Bayer process, it is produced from inorganic borates, including <a href="/wiki/Borosilicate_glass" title="Borosilicate glass">borosilicate glass</a><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Borax" title="Borax">borax</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">7</sub></span>): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">7</sub> + 16 Na + 8 H<sub class="template-chem2-sub">2</sub> + 7 SiO<sub class="template-chem2-sub">2</sub> → 4 NaBH<sub class="template-chem2-sub">4</sub> + 7 Na<sub class="template-chem2-sub">2</sub>SiO<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>Magnesium is a less expensive reductant, and could in principle be used instead:<sup id="cite_ref-Production_1_17-0" class="reference"><a href="#cite_note-Production_1-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Production_2_18-0" class="reference"><a href="#cite_note-Production_2-18"><span class="cite-bracket">[</span>18<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">8 MgH<sub class="template-chem2-sub">2</sub> + Na<sub class="template-chem2-sub">2</sub>B<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">7</sub> + Na<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">3</sub> → 4 NaBH<sub class="template-chem2-sub">4</sub> + 8 MgO + CO<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>and </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 MgH<sub class="template-chem2-sub">2</sub> + NaBO<sub class="template-chem2-sub">2</sub> → NaBH<sub class="template-chem2-sub">4</sub> + 2 MgO</span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=4" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Organic_synthesis">Organic synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=5" title="Edit section: Organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> <a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">reduces many organic carbonyls</a>, depending on the conditions. Most typically, it is used in the laboratory for converting ketones and aldehydes to alcohols.<sup id="cite_ref-eros_6-1" class="reference"><a href="#cite_note-eros-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> These reductions proceed in two stages, formation of the alkoxide followed by hydrolysis: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub> + 4 R<sub class="template-chem2-sub">2</sub>C=O → NaO−CHR<sub class="template-chem2-sub">2</sub> + B(O−CHR<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaO−CHR<sub class="template-chem2-sub">2</sub> + B(O−CHR<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub> + 4 H<sub class="template-chem2-sub">2</sub>O → 4 HO−CHR<sub class="template-chem2-sub">2</sub> + NaOH + B(OH)<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>It also efficiently reduces <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a>, <a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">anhydrides</a>, α-hydroxy<a href="/wiki/Lactonase" title="Lactonase">lactones</a>, <a href="/wiki/Thioester" title="Thioester">thioesters</a>, and <a href="/wiki/Imine" title="Imine">imines</a> at room temperature or below. It reduces esters slowly and inefficiently with excess reagent and/or elevated temperatures, while carboxylic acids and amides are not reduced at all.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Nevertheless, an alcohol, often methanol or ethanol, is generally the solvent of choice for sodium borohydride reductions of ketones and aldehydes. The mechanism of ketone and aldehyde reduction has been scrutinized by kinetic studies, and contrary to popular depictions in textbooks, the mechanism does not involve a 4-membered transition state like alkene hydroboration,<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> or a six-membered transition state involving a molecule of the alcohol solvent.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Hydrogen-bonding activation is required, as no reduction occurs in an aprotic solvent like <a href="/wiki/Diglyme" title="Diglyme">diglyme</a>. However, the rate order in alcohol is 1.5, while carbonyl compound and borohydride are both first order, suggesting a mechanism more complex than one involving a six-membered transition state that includes only a single alcohol molecule. It was suggested that the simultaneous activation of the carbonyl compound and borohydride occurs, via interaction with the alcohol and alkoxide ion, respectively, and that the reaction proceeds through an open transition state.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>α,β-Unsaturated ketones tend to be reduced by <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> in a 1,4-sense, although mixtures are often formed. Addition of cerium chloride improves the <a href="/wiki/Chemoselectivity" title="Chemoselectivity">selectivity</a> for 1,2-reduction of unsaturated ketones (<a href="/wiki/Luche_reduction" title="Luche reduction">Luche reduction</a>). α,β-Unsaturated esters also undergo 1,4-reduction in the presence of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span>.<sup id="cite_ref-eEROS_9-3" class="reference"><a href="#cite_note-eEROS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span>-MeOH system, formed by the addition of <a href="/wiki/Methanol" title="Methanol">methanol</a> to sodium borohydride in refluxing THF, reduces esters to the corresponding alcohols.<sup id="cite_ref-Costa_24-0" class="reference"><a href="#cite_note-Costa-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Mixing water or an alcohol with the borohydride converts some of it into unstable hydride ester, which is more efficient at reduction, but the reductant eventually decomposes spontaneously to produce hydrogen gas and borates. The same reaction can also occur intramolecularly: an α-ketoester converts into a diol, since the alcohol produced attacks the borohydride to produce an ester of the borohydride, which then reduces the neighboring ester.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>The reactivity of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> can be enhanced or augmented by a variety of compounds.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Many additives for modifying the reactivity of sodium borohydride have been developed as indicated by the following incomplete listing. </p> <table class="wikitable"> <caption>Additives for sodium borohydride </caption> <tbody><tr> <th>additive</th> <th>synthetic applications</th> <th>page in Smith and March<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup></th> <th>comment </th></tr> <tr> <td><a href="/wiki/Aluminium_trichloride" class="mw-redirect" title="Aluminium trichloride">AlCl<sub>3</sub></a></td> <td>reduction of ketones to methylene</td> <td>1837</td> <td> </td></tr> <tr> <td><a href="/wiki/Bismuth_trichloride" class="mw-redirect" title="Bismuth trichloride">BiCl<sub>3</sub></a></td> <td>converts epoxides to allylic alcohols</td> <td>1316</td> <td> </td></tr> <tr> <td><a href="/wiki/Diphenyl_ditelluride" title="Diphenyl ditelluride">(C<sub>6</sub>H<sub>5</sub>Te)<sub>2</sub></a></td> <td>reduction of nitroarenes</td> <td>1862 </td></tr> <tr> <td><a href="/wiki/Cerium(III)_chloride" title="Cerium(III) chloride">CeCl<sub>3</sub></a></td> <td>reduction of ketones in the presence of aldehydes</td> <td>1794</td> <td><a href="/wiki/Luche_reduction" title="Luche reduction">Luche reduction</a> </td></tr> <tr> <td><a href="/wiki/Cobalt_dichloride" class="mw-redirect" title="Cobalt dichloride">CoCl<sub>2</sub></a></td> <td>reduction of azides to amines</td> <td>1822</td> <td> </td></tr> <tr> <td><a href="/wiki/Indium_trichloride" class="mw-redirect" title="Indium trichloride">InCl<sub>3</sub></a></td> <td>hydrogenolysis of alkyl bromides, double reduction of unsaturated ketones</td> <td>1825, 1793</td> <td> </td></tr> <tr> <td><a href="/wiki/Lithium_chloride" title="Lithium chloride">LiCl</a></td> <td>amine oxides to amines</td> <td>1846</td> <td><a href="/wiki/Lithium_borohydride" title="Lithium borohydride">lithium borohydride</a> </td></tr> <tr> <td><a href="/wiki/Nickel(II)_chloride" title="Nickel(II) chloride">NiCl<sub>2</sub></a></td> <td>deoxygenation of sulfoxides, hydrogenolysis of aryl tosylates, desulfurization, reduction of nitriles</td> <td>1851,1831, 991, 1814</td> <td><a href="/wiki/Nickel_boride" class="mw-redirect" title="Nickel boride">nickel boride</a> </td></tr> <tr> <td><a href="/wiki/Titanium_tetrachloride" title="Titanium tetrachloride">TiCl<sub>4</sub></a></td> <td>denitrosatation of <a href="/wiki/Nitrosamine" title="Nitrosamine">nitrosamines</a></td> <td>1823</td> <td> </td></tr> <tr> <td><a href="/wiki/Zinc_chloride" title="Zinc chloride">ZnCl<sub>2</sub></a></td> <td>reduction of aldehydes</td> <td>1793</td> <td> </td></tr> <tr> <td><a href="/wiki/Zirconium_tetrachloride" class="mw-redirect" title="Zirconium tetrachloride">ZrCl<sub>4</sub></a></td> <td>reduction of disulfides, reduction of azides to amines, cleavage of allyl aryl ethers</td> <td>1853, 1822, 582</td> <td> </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=6" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxidation with <a href="/wiki/Iodine" title="Iodine">iodine</a> in <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> gives <a href="/wiki/Borane%E2%80%93tetrahydrofuran" title="Borane–tetrahydrofuran">borane–tetrahydrofuran</a>, which can reduce carboxylic acids to alcohols.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Partial oxidation of <a href="/wiki/Borohydride" title="Borohydride">borohydride</a> with iodine gives <a href="/wiki/Octahydrotriborate" title="Octahydrotriborate">octahydrotriborate</a>:<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<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">3 [BH<sub class="template-chem2-sub">4</sub>]<sup class="template-chem2-sup">−</sup> + I<sub class="template-chem2-sub">2</sub> → [B<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">8</sub>]<sup class="template-chem2-sup">−</sup> + 2 H<sub class="template-chem2-sub">2</sub> + 2 I<sup class="template-chem2-sup">−</sup></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Coordination_chemistry">Coordination chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=7" title="Edit section: Coordination chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[BH<sub class="template-chem2-sub">4</sub>]<sup class="template-chem2-sup">−</sup></span> is a <a href="/wiki/Ligand" title="Ligand">ligand</a> for metal ions. Such borohydride complexes are often prepared by the action of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> (or the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">LiBH<sub class="template-chem2-sub">4</sub></span>) on the corresponding metal halide. One example is the <a href="/wiki/Titanocene" class="mw-redirect" title="Titanocene">titanocene</a> derivative:<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<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 (C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>TiCl<sub class="template-chem2-sub">2</sub> + 4 NaBH<sub class="template-chem2-sub">4</sub> → 2 (C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>TiBH<sub class="template-chem2-sub">4</sub> + 4 NaCl + B<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">6</sub> + H<sub class="template-chem2-sub">2</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Protonolysis_and_hydrolysis">Protonolysis and hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=8" title="Edit section: Protonolysis and hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub></span> reacts with water and alcohols, with evolution of hydrogen gas and formation of the corresponding borate, the reaction being especially fast at low pH. Exploiting this reactivity, sodium borohydride has been studied as a prototypes of the <a href="/wiki/Direct_borohydride_fuel_cell" title="Direct borohydride fuel cell">direct borohydride fuel cell</a>. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaBH<sub class="template-chem2-sub">4</sub> + 2 H<sub class="template-chem2-sub">2</sub>O → NaBO<sub class="template-chem2-sub">2</sub> + 4 H<sub class="template-chem2-sub">2</sub></span> (ΔH < 0)</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=9" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Paper_manufacture">Paper manufacture</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=10" title="Edit section: Paper manufacture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The dominant application of sodium borohydride is the production of <a href="/wiki/Sodium_dithionite" title="Sodium dithionite">sodium dithionite</a> from sulfur dioxide: Sodium dithionite is used as a bleaching agent for wood pulp and in the dyeing industry. </p><p>It has been tested as pretreatment for pulping of wood, but is too costly to be commercialized.<sup id="cite_ref-Ullmann_15-1" class="reference"><a href="#cite_note-Ullmann-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kraftpulping_32-0" class="reference"><a href="#cite_note-kraftpulping-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_synthesis">Chemical synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=11" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium borohydride <a href="/wiki/Organic_reduction" class="mw-redirect" title="Organic reduction">reduces</a> <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> and <a href="/wiki/Ketone" title="Ketone">ketones</a> to give the related <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>. This reaction is used in the production of various antibiotics including <a href="/wiki/Chloramphenicol" title="Chloramphenicol">chloramphenicol</a>, <a href="/wiki/Dihydrostreptomycin" title="Dihydrostreptomycin">dihydrostreptomycin</a>, and <a href="/wiki/Thiophenicol" class="mw-redirect" title="Thiophenicol">thiophenicol</a>. Various steroids and <a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a> are prepared using sodium borohydride in at least one step.<sup id="cite_ref-Ullmann_15-2" class="reference"><a href="#cite_note-Ullmann-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Niche_or_abandoned_applications">Niche or abandoned applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=12" title="Edit section: Niche or abandoned applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sodium borohydride has been considered as a way to <a href="/wiki/Hydrogen_storage" title="Hydrogen storage">store hydrogen</a> for <a href="/wiki/Hydrogen_fuel" class="mw-redirect" title="Hydrogen fuel">hydrogen-fueled</a> vehicles, as it is safer (being stable in dry air) and more efficient on a weight basis than most other alternatives.<sup id="cite_ref-park2007_33-0" class="reference"><a href="#cite_note-park2007-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-zpli2003_34-0" class="reference"><a href="#cite_note-zpli2003-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> The hydrogen can be released by simple hydrolysis of the borohydride. However, such a usage would need a cheap, relatively simple, and energy-efficient process to recycle the hydrolysis product, <a href="/wiki/Sodium_metaborate" title="Sodium metaborate">sodium metaborate</a>, back to the borohydride. No such process was available as of 2007.<sup id="cite_ref-atiy2007_35-0" class="reference"><a href="#cite_note-atiy2007-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Although practical temperatures and pressures for hydrogen storage have not been achieved, in 2012 a core–shell <a href="/wiki/Nanostructure" title="Nanostructure">nanostructure</a> of sodium borohydride was used to store, release and reabsorb hydrogen under moderate conditions.<sup id="cite_ref-gary2012_36-0" class="reference"><a href="#cite_note-gary2012-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>Skilled professional conservator/restorers have used sodium borohydride to minimize or reverse <a href="/wiki/Foxing" title="Foxing">foxing</a> in old books and documents.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<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_borohydride&action=edit&section=13" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many derivatives and analogues of sodium borohydride exhibit modified reactivity of value in organic synthesis.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Sodium_triacetoxyborohydride" title="Sodium triacetoxyborohydride">Sodium triacetoxyborohydride</a>, a milder reductant owing to the presence of more electron-withdrawing acetate in place of hydride.</li> <li><a href="/wiki/Sodium_triethylborohydride" title="Sodium triethylborohydride">Sodium triethylborohydride</a>, a stronger reductant owing to the presence of electron-donating ethyl groups in place of hydride.</li> <li><a href="/wiki/Sodium_cyanoborohydride" title="Sodium cyanoborohydride">sodium cyanoborohydride</a>, a milder reductant owing to the presence of more electron-withdrawing cyanide in place of hydride. Useful for reductive aminations.</li></ul> <ul><li><a href="/wiki/Lithium_borohydride" title="Lithium borohydride">Lithium borohydride</a>, a more strongly reducing reagent.</li> <li><a href="/wiki/L-selectride" title="L-selectride">L-selectride</a> (lithium tri-<i>sec</i>-butylborohydride), a more strongly reducing derivative.</li></ul> <ul><li><a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">Lithium aluminium hydride</a>, a more strongly reducing reagent, capable of reducing esters and amides.</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_borohydride&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-crc-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-crc_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-crc_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-crc_1-2"><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="CITEREFHaynes,_William_M.2011" class="citation book cs1">Haynes, William M., ed. (2011). <a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics"><i>CRC Handbook of Chemistry and Physics</i></a> (92nd ed.). <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. p. 4.89. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1439855119" title="Special:BookSources/978-1439855119"><bdi>978-1439855119</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.pages=4.89&rft.edition=92nd&rft.pub=CRC+Press&rft.date=2011&rft.isbn=978-1439855119&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+borohydride" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFord,_P._T._and_Powell,_H._M.1954" class="citation journal cs1">Ford, P. T. and Powell, H. M. (1954). <a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X54002034">"The unit cell of potassium borohydride, KBH<sub>4</sub>, at 90° K"</a>. <i>Acta Crystallogr</i>. <b>7</b> (8): 604–605. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1954AcCry...7..604F">1954AcCry...7..604F</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X54002034">10.1107/S0365110X54002034</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallogr&rft.atitle=The+unit+cell+of+potassium+borohydride%2C+KBH%3Csub%3E4%3C%2Fsub%3E%2C+at+90%C2%B0+K&rft.volume=7&rft.issue=8&rft.pages=604-605&rft.date=1954&rft_id=info%3Adoi%2F10.1107%2FS0365110X54002034&rft_id=info%3Abibcode%2F1954AcCry...7..604F&rft.au=Ford%2C+P.+T.+and+Powell%2C+H.+M.&rft_id=https%3A%2F%2Fdoi.org%2F10.1107%252FS0365110X54002034&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+borohydride" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/930681942"><i>CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data</i></a>. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4987-5428-6" title="Special:BookSources/978-1-4987-5428-6"><bdi>978-1-4987-5428-6</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/930681942">930681942</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+handbook+of+chemistry+and+physics+%3A+a+ready-reference+book+of+chemical+and+physical+data.&rft.place=Boca+Raton%2C+Florida&rft.edition=2016-2017%2C+97th&rft.date=2016&rft_id=info%3Aoclcnum%2F930681942&rft.isbn=978-1-4987-5428-6&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F930681942&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+borohydride" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>) CS1 maint: others (<a href="/wiki/Category:CS1_maint:_others" title="Category:CS1 maint: others">link</a>)</span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=005740&lang=en">Record of <i>Sodium borohydride</i></a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a>, accessed on 2023-11-09. </span> </li> <li id="cite_note-google-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-google_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBusch,_D.H.2009" class="citation book cs1">Busch, D.H. (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=XktiIRlSBlkC"><i>Inorganic Syntheses</i></a>. Vol. 20. Wiley. p. 137. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470132869" title="Special:BookSources/9780470132869"><bdi>9780470132869</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">20 May</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Inorganic+Syntheses&rft.pages=137&rft.pub=Wiley&rft.date=2009&rft.isbn=9780470132869&rft.au=Busch%2C+D.H.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXktiIRlSBlkC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+borohydride" class="Z3988"></span></span> </li> <li id="cite_note-eros-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-eros_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-eros_6-1"><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="CITEREFBanfiNarisanoRivaStiasni2014" class="citation book cs1">Banfi, Luca; Narisano, Enrica; Riva, Renata; Stiasni, Nikola; Hiersemann, Martin; Yamada, Tohru; Tsubo, Tatsuyuki (2014). 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I.; <a href="/wiki/Herbert_C._Brown" title="Herbert C. Brown">Brown, H. C.</a>; Abraham, B.; Bond, A. C.; Davidson, N.; Finholt, A. E.; Gilbreath, J. R.; Hoekstra, H.; Horvitz, L.; Hyde, E. K.; Katz, J. J.; Knight, J.; Lad, R. A.; Mayfield, D. L.; Rapp, L.; Ritter, D. M.; Schwartz, A. M.; Sheft, I.; Tuck, L. D.; Walker, A. O. (1953). "New developments in the chemistry of diborane and the borohydrides. General summary". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. 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Davis (2007): "Separation of sodium metaborate from sodium borohydride using nanofiltration membranes for hydrogen storage application". <i>International Journal of Hydrogen Energy</i>, volume 32, issue 2, pages 229-236. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ijhydene.2006.06.003">10.1016/j.ijhydene.2006.06.003</a></span> </li> <li id="cite_note-gary2012-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-gary2012_36-0">^</a></b></span> <span class="reference-text">Stuart Gary, "<a rel="nofollow" class="external text" href="http://www.abc.net.au/science/articles/2012/08/16/3569478.htm">Hydrogen storage no longer up in the air</a>" in <i><a href="/wiki/ABC_News_and_Current_Affairs" class="mw-redirect" title="ABC News and Current Affairs">ABC Science</a></i> 16 August 2012, citing <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChristianAguey-Zinsou2012" class="citation journal cs1"><a href="/wiki/Meganne_Christian" title="Meganne Christian">Christian, Meganne</a>; Aguey-Zinsou, Kondo François (2012). "Core–Shell Strategy Leading to High Reversible Hydrogen Storage Capacity for NaBH<sub>4</sub>". <i><a href="/wiki/ACS_Nano" title="ACS Nano">ACS Nano</a></i>. <b>6</b> (9): 7739–7751. <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%2Fnn3030018">10.1021/nn3030018</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/22873406">22873406</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Nano&rft.atitle=Core%E2%80%93Shell+Strategy+Leading+to+High+Reversible+Hydrogen+Storage+Capacity+for+NaBH%3Csub%3E4%3C%2Fsub%3E&rft.volume=6&rft.issue=9&rft.pages=7739-7751&rft.date=2012&rft_id=info%3Adoi%2F10.1021%2Fnn3030018&rft_id=info%3Apmid%2F22873406&rft.aulast=Christian&rft.aufirst=Meganne&rft.au=Aguey-Zinsou%2C+Kondo+Fran%C3%A7ois&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+borohydride" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMasters" class="citation web cs1">Masters, Kristin. <a rel="nofollow" class="external text" href="https://blog.bookstellyouwhy.com/bid/230209/how-to-prevent-and-reverse-foxing-in-rare-books">"How to Prevent and Reverse Foxing in Rare Books"</a>. <i>bookstellyouwhy.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">3 April</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=bookstellyouwhy.com&rft.atitle=How+to+Prevent+and+Reverse+Foxing+in+Rare+Books&rft.aulast=Masters&rft.aufirst=Kristin&rft_id=https%3A%2F%2Fblog.bookstellyouwhy.com%2Fbid%2F230209%2Fhow-to-prevent-and-reverse-foxing-in-rare-books&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASodium+borohydride" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text">Seyden-Penne, J. (1991) <a rel="nofollow" class="external text" href="http://rushim.ru/books/mechanizms/reductions.pdf"><i>Reductions by the Alumino- and Borohydrides in Organic Synthesis</i></a>. VCH–Lavoisier: Paris. p. 9. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-19036-3" title="Special:BookSources/978-0-471-19036-3">978-0-471-19036-3</a></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sodium_borohydride&action=edit&section=15" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060209040519/http://www.npi.gov.au/database/substance-info/profiles/15.html">National Pollutant Inventory – Boron and compounds</a></li> <li><a rel="nofollow" class="external text" href="https://archive.today/20130202223031/http://www.sodiumborohydride.com/wcm/products/product_detail.page?display-mode=msds&product=1120465&application=1120785">MSDS for Sodium Borohydride</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20050305180812/http://merit.hydrogen.co.jp/">Materials & Energy Research Institute Tokyo, Ltd.</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20051201011849/http://www.sodiumborohydride.com/technical.html">Chemo- and stereoselectivity using Borohydride reagents</a></li> <li><a rel="nofollow" class="external text" href="http://www.sciencelab.com/msds.php?msdsId=9924969">Material Safety Data Sheet</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170710022359/http://www.sciencelab.com/msds.php?msdsId=9924969">Archived</a> 2017-07-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li></ul> <div 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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 class="mw-selflink selflink">NaBH<sub>4</sub></a></li> <li><a href="/wiki/Sodium_cyanoborohydride" title="Sodium cyanoborohydride">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> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407895#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" 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