Sodium bis(2-methoxyethoxy)aluminium hydride

<h2 id="comparison-with-lithium-aluminium-hydride">Comparison with lithium aluminium hydride</h2>
<p>As a <a href="/facts/Reagent/c3GLInCu">reagent</a>, SMEAH is comparable with <a href="/facts/Lithium_aluminium_hydride/QMMhdqEy">lithium aluminium hydride</a> (LAH, LiAlH4).
</p><p>It is a safer alternative to LAH and related hydrides. SMEAH exhibits similar reducing effects, but does not have the inconvenient <a href="/facts/Pyrophoricity/1b8Sl2AJ">pyrophoric</a> nature, short shelf-life, or limited <a href="/facts/Solubility/kLE9h3Jb">solubility</a> of LAH. Upon contact with air and moisture, SMEAH reacts exothermically but does not ignite, and tolerates temperatures up to 200°C. Under dry conditions it has unlimited shelf life. It is soluble in aromatic solvents, whereas LAH is only soluble in ethers. For example, a solution greater than 70 wt.% concentration in <a href="/facts/Toluene/Pzdt8dwD">toluene</a> is commercially available. The reagent can be modified to effect partial reductions.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a>
</p><p>SMEAH in toluene under reflux has been used to reduce aliphatic <i>p-</i>toluenesulfonamides (TsNR2) to the corresponding free amines and is one of the few reagents that can carry out this challenging reduction in general settings.  Notably, LiAlH4 does not reduce this functional group unless forcing conditions are used.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a>
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<h2 id="external-links">External links</h2>
<ul><li><a href="https://www.organic-chemistry.org/chemicals/reductions/sodiumbis(2-methoxyethoxy)aluminumhydride-red-al.shtm">"Red-Al, Sodium bis(2-methoxyethoxy)aluminumhydride"</a>. Organic Chemistry.</li></ul>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>Gugelchuk, M.; Silva, L. F. III; Vasconcelos, R. S.; Quintiliano, S. A. P. (2007). "Sodium Bis(2-methoxyethoxy)aluminum Hydride". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/9780470842898.rs049.pub2. ISBN 978-0471936237. <a href="978-0471936237" target="_blank">978-0471936237</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>Gugelchuk, M.; Silva, L. F. III; Vasconcelos, R. S.; Quintiliano, S. A. P. (2007). "Sodium Bis(2-methoxyethoxy)aluminum Hydride". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/9780470842898.rs049.pub2. ISBN 978-0471936237. <a href="978-0471936237" target="_blank">978-0471936237</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
<li id="fn:3"><p>Gugelchuk, M.; Silva, L. F. III; Vasconcelos, R. S.; Quintiliano, S. A. P. (2007). "Sodium Bis(2-methoxyethoxy)aluminum Hydride". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/9780470842898.rs049.pub2. ISBN 978-0471936237. <a href="978-0471936237" target="_blank">978-0471936237</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li>
<li id="fn:4"><p>Smith, Michael B. (2011). Organic Synthesis. Cambridge, Mass.: Academic Press. p. 368. ISBN 9780124158849. <a href="9780124158849" target="_blank">9780124158849</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li>
</ol>

Sodium bis(2-methoxyethoxy)aluminium hydride open-in-new

Sodium bis(2-methoxyethoxy)aluminium hydride