View source for Sodium bis(2-methoxyethoxy)aluminium hydride

{{Chembox
|ImageFile = Sodium bis(2-methoxyethoxy)aluminumhydride.svg
|ImageFile_Ref = {{Chemboximage|correct|??}}
|ImageName = Structural formula of sodium bis(2-methoxyethoxy)aluminium hydride
|IUPACName = Sodium bis(2-methoxyethoxy)aluminium hydride
|OtherNames = Red-Al, Synhydrid, Vitride
|Section1={{Chembox Identifiers
|Abbreviations = SMEAH
|CASNo = 22722-98-1
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 04JL3B71VP
|PubChem = 16684438
|ChemSpiderID = 21169529
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|SMILES = [Na+].COCCO[AlH2-]OCCOC
|SMILES1 = [H][Al-](OCCOC)([H])OCCOC.[Na+]
|StdInChI = 1S/2C3H7O2.Al.Na.2H/c2*1-5-3-2-4;;;;/h2*2-3H2,1H3;;;;/q2*-1;2*+1;;
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = XJIQVZMZXHEYOY-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
|C=6 | H=16 | Al=1 | Na=1 | O=4
|Density = 1.122 g/cm<sup>3</sup> (solid)<ref name=eEROS/><br>1.036 g/mL (>60% solution)
|Viscosity = 65.1 cps (70% solution){{citation needed|date=October 2014}}
|Appearance = Transparent crystals
}}
|Section3={{Chembox Hazards
|MainHazards = Highly flammable; moisture sensitive; potent skin irritant<ref name=eEROS/>
}}
}}
'''Sodium bis(2-methoxyethoxy)aluminium hydride''' ('''SMEAH''';<ref name=eEROS/> trade names '''Red-Al''',  '''Synhydrid''', '''Vitride''') is a hydride reductant with the [[chemical formula|formula]] NaAlH{{sub|2}}(OCH{{sub|2}}CH{{sub|2}}OCH{{sub|3}}){{sub|2}}. The trade name Red-Al refers to its being a ''red''ucing ''al''uminium compound. It is used predominantly as a [[reducing agent]] in [[organic synthesis]].  The compound features a [[Tetrahedral molecular geometry|tetrahedral]] aluminium center attached to two [[hydride]] and two [[alkoxide]] groups, the latter derived from [[2-Methoxyethanol|2-methoxyethanol]]. Commercial solutions are colorless/pale yellow and viscous. At low temperatures (below -60°C), the solution solidifies to a glassy pulverizable substance with no sharp melting point.
SMEAH is a versatile hydride reducing agent. It readily converts [[epoxide]]s, [[aldehyde]]s, [[ketone]]s, [[carboxylic acid]]s, [[ester]]s, [[acyl halide]]s, and [[anhydride]]s to the corresponding [[Alcohol (chemistry)|alcohol]]s. Nitrogen derivates such as [[amide]]s, [[nitrile]]s, [[imine]]s, and most other organonitrogen compounds are reduced to the corresponding [[amine]]s. Nitroarenes can be converted to azoxyarenes, azoarenes, or hydroazoarenes, depending on the reaction conditions.<ref name=eEROS>{{cite encyclopedia |author1=Gugelchuk, M. |author2=Silva, L. F. III |author3=Vasconcelos, R. S. |author4=Quintiliano, S. A. P. | chapter = Sodium Bis(2-methoxyethoxy)aluminum Hydride | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | publisher = John Wiley & Sons | year = 2007 | location = New York | doi =10.1002/9780470842898.rs049.pub2|isbn=978-0471936237 }}</ref>
Some common functional group reductions using SMEAH can be found below:
[[File:Red-Al Reductions.png|thumb|center|500px]]
==Comparison with lithium aluminium hydride==
As a [[reagent]], SMEAH is comparable with [[lithium aluminium hydride]] (LAH, LiAlH{{sub|4}}).
It is a safer alternative to LAH and related hydrides. SMEAH exhibits similar reducing effects, but does not have the inconvenient [[pyrophoricity|pyrophoric]] nature, short shelf-life, or limited [[solubility]] 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&nbsp;wt.% concentration in [[toluene]] is commercially available. The reagent can be modified to effect partial reductions.<ref name=eEROS/>
SMEAH in toluene under reflux has been used to reduce aliphatic ''p-''toluenesulfonamides (TsNR{{sub|2}}) to the corresponding free amines and is one of the few reagents that can carry out this challenging reduction in general settings.  Notably, LiAlH{{sub|4}} does not reduce this functional group unless forcing conditions are used.<ref>{{cite book|title=Organic Synthesis|last=Smith|first=Michael B.|publisher=Academic Press|year=2011|isbn=9780124158849|location=Cambridge, Mass.|pages=368}}</ref>
==References==
{{Reflist}}
==External links==
* {{ cite web | url = https://www.organic-chemistry.org/chemicals/reductions/sodiumbis(2-methoxyethoxy)aluminumhydride-red-al.shtm | title = Red-Al, Sodium bis(2-methoxyethoxy)aluminumhydride | publisher = Organic Chemistry }}
{{Sodium compounds}}
{{Aluminium compounds}}
[[Category:Hydrido complexes]]
[[Category:Reducing agents]]
[[Category:Aluminium complexes]]
[[Category:Alkoxides]]
[[Category:Sodium compounds]]