Sodium bis(2-methoxyethoxy)aluminium hydride

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Sodium bis(2-methoxyethoxy)aluminium hydride - Wikipedia

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Sodium bis(2-methoxyethoxy)aluminium hydride
Names

IUPAC name Sodium bis(2-methoxyethoxy)aluminium hydride
Other names Red-Al, Synhydrid, Vitride
Identifiers
CAS Number	22722-98-1^Y
3D model (JSmol)	Interactive image Interactive image
Abbreviations	SMEAH
ChemSpider	21169529^Y
ECHA InfoCard	100.041.056
PubChem CID	16684438
UNII	04JL3B71VP^Y
CompTox Dashboard (EPA)	DTXSID90894051
InChI InChI=1S/2C3H7O2.Al.Na.2H/c21-5-3-2-4;;;;/h22-3H2,1H3;;;;/q2-1;2+1;;^Y Key: XJIQVZMZXHEYOY-UHFFFAOYSA-N^Y
SMILES [Na+].COCCO[AlH2-]OCCOC [H][Al-](OCCOC)([H])OCCOC.[Na+]
Properties
Chemical formula	C₆H₁₆AlNaO₄
Molar mass	202.161 g·mol⁻¹
Appearance	Transparent crystals
Density	1.122 g/cm³ (solid)^[1] 1.036 g/mL (>60% solution)
Viscosity	65.1 cps (70% solution)^{[citation needed]}
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly flammable; moisture sensitive; potent skin irritant^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH;^[1] trade names Red-Al, Synhydrid, Vitride) is a hydride reductant with the formula NaAlH₂(OCH₂CH₂OCH₃)₂. The trade name Red-Al refers to its being a reducing aluminium compound. It is used predominantly as a reducing agent in organic synthesis. The compound features a tetrahedral aluminium center attached to two hydride and two alkoxide groups, the latter derived from 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 epoxides, aldehydes, ketones, carboxylic acids, esters, acyl halides, and anhydrides to the corresponding alcohols. Nitrogen derivates such as amides, nitriles, imines, and most other organonitrogen compounds are reduced to the corresponding amines. Nitroarenes can be converted to azoxyarenes, azoarenes, or hydroazoarenes, depending on the reaction conditions.^[1]

Some common functional group reductions using SMEAH can be found below:

Comparison with lithium aluminium hydride

As a reagent, SMEAH is comparable with lithium aluminium hydride (LAH, LiAlH₄).

It is a safer alternative to LAH and related hydrides. SMEAH exhibits similar reducing effects, but does not have the inconvenient 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 wt.% concentration in toluene is commercially available. The reagent can be modified to effect partial reductions.^[1]

SMEAH in toluene under reflux has been used to reduce aliphatic p-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.^[2]

References

^ ^a ^b ^c ^d ^e 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.
^ Smith, Michael B. (2011). Organic Synthesis. Cambridge, Mass.: Academic Press. p. 368. ISBN 9780124158849.

External links

"Red-Al, Sodium bis(2-methoxyethoxy)aluminumhydride". Organic Chemistry.

Sodium compounds

Inorganic

Halides	NaF NaHF₂ NaCl NaBr NaI NaAt
Chalcogenides	NaO₃ NaO₂ Na₂O Na₂O₂ NaOH NaOD Na₂S NaSH Na₂Se NaSeH Na₂Te NaHTe Na₂Po
Pnictogenides	Na₃N NaN₃ NaNH₂ Na₃P Na₃As
Oxyhalides	NaClO NaClO₂ NaClO₃ NaClO₄ NaBrO NaBrO₂ NaBrO₃ NaBrO₄ NaIO₃ NaIO₄
Oxychalcogenides	Na₂SO₃ Na₂SO₄ NaHSO₃ NaHSO₄ Na₂S₂O₃ Na₂S₂O₄ Na₂S₂O₅ Na₂S₂O₆ Na₂S₂O₇ Na₂S₂O₈ Na₂SeO₃ Na₂SeO₄ NaHSeO₃ Na₂TeO₃
Oxypnictogenides	NaNO₂ NaNO₃ Na₂N₂O₂ NaH₂PO₄ NaPO₂H₂ Na₂HPO₃ Na₂PO₃F Na₃PS₂O₂ Na₃PO₄ Na₅P₃O₁₀ Na₄P₂O₇ Na₂H₂P₂O₇ Na₃AsO₃ Na₃AsO₄ Na₂HAsO₄ NaH₂AsO₄ NaSbO₃
Others	NaAlH₄ NaAlO₂ Na₃AlF₆ NaAl(SO₄)₂ NaAuCl₄ NaSbF₆ NaAsF₆ Na₂TiF₆ NaBH₄ NaBH₃(CN) NaBO₂ Na₂B₄O₇ Na₂B₂O₉ Na₂B₈O₁₃ NaBiO₃ NaCN NaCNO NaCoO₂ NaH NaHCO₃ Na₄XeO₆ NaHXeO₄ NaMnO₄ NaOCN NaReO₄ NaSCN NaTcO₃ NaTcO₄ NaVO₃ Na₂CO₃ Na₂C₂O₄ Na₂C₃S₅ Na₂CrO₄ Na₂Cr₂O₇ Na₂Cr₃O₁₀ Na₂GeO₃ Na₂He Na₂[Fe(CO)₄] Na₂MnO₄ Na₂MoO₄ Na₃IrCl₆ Na₂PtCl₆ Na₂O(UO₃)₂ Na₂S₄O₆ Na₂SiO₃ Na₂TiO₃ Na₂U₂O₇ Na₂WO₄ Na₂Zn(OH)₄ Na₃VO₄ Na₆V₁₀O₂₈ Na₄Fe(CN)₆ Na₃Fe(CN)₆ Na₃Fe(C₂O₄)₃ Na₄SiO₄ Na₂SiF₆ Na₃[Co(NO₂)₆] NaNSi₂(CH₃)₆ Na₂PdCl₄

Organic

Aluminium compounds

Al(I)

Organoaluminium(I) compounds	Al(C₅(CH₃)₅)

Al(II)

Al(III)

Alums	(NH₄)Al(SO₄)₂ KAl(SO₄)₂ NaAl(SO₄)₂
Organoaluminium(III) compounds	Al(C₃H₅O₃)₃ C ₃₆H ₆₉AlO ₆ (Al(CH₃)₃)₂ (Al(C₂H₅)₃)₂ Al(CH₂CH(CH₃)₂)₃ Al(C₂H₅)₂Cl Al(C₂H₅)₂CN Al(CH₂CH(CH₃)₂)₂H Al(C₂H₅)₂Cl₂C₂H₅Cl Ti(C₅H₅)₂CH₂ClAl(CH₃)₂

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