Sodium bis(2-methoxyethoxy)aluminium hydride

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 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	SMEAH
ChemSpider	21169529 ;
ECHA InfoCard	100.041.056
PubChem CID	16684438;
UNII	04JL3B71VP ;
CompTox Dashboard (EPA)	DTXSID90894051 ;
	InChI InChI=1S/2C3H7O2.Al.Na.2H/c21-5-3-2-4;;;;/h22-3H2,1H3;;;;/q2-1;2+1;; Key: XJIQVZMZXHEYOY-UHFFFAOYSA-N ;
	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); 1.036 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
	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:

^ ^a ^b ^c ^d 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.

[eEROS-1] 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.

[1]