Sodium bis(2-methoxyethoxy)aluminumhydride
aluminumhydride.svg.png) | |
| Names | |
|---|---|
| IUPAC name
Sodium bis(2-methoxyethoxy)aluminumhydride | |
| Other names
Red-Al, Synhydrid, Vitride | |
| Identifiers | |
22722-98-1  | |
| Abbreviations | SMEAH |
| ChemSpider | 21169529  |
| Jmol interactive 3D | Image Image |
| PubChem | 16684438 |
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| Properties | |
| C6H16AlNaO4 | |
| Molar mass | 202.16 g·mol−1 |
| Appearance | Transparent crystals |
| Density | 1.036 g/mL (>60% solution) |
| Viscosity | 65.1 cps (70% solution) |
| Hazards | |
| Main hazards | Unstable toward water |
| 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)aluminumhydride (trade names Red-Al, Synhydrid, Vitride) is an organoaluminium compound with the formula NaAlH2(OCH2CH2OCH3)2. The trade name Red-Al refers to its being a reducing aluminium compound. It is a 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 colourless/pale yellow and viscous. At low temperatures, the solution solidifies to a glassy pulverizable substance. No sharp melting point was found.
Sodium bis(2-methoxyethoxy)aluminumhydride is a versatile hydride reducing agent. It readily converts aldehydes, ketones, carboxylic acids, esters, acyl halides, and anhydrides to primary alcohols. The cyclic compounds such a lactones and epoxides are reduced to diols. Nitrogen derivates such a 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 sodium bis(2-methoxyethoxy)aluminumhydride can be found below:
Comparison with lithium aluminium hydride
As a reagent, sodium bis(2-methoxyethoxy)aluminumhydride is comparable with lithium aluminum hydride (LAH, LiAlH4).
It is a safer substitute for LAH and related hydrides. Sodium bis(2-methoxyethoxy)aluminumhydride 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, Sodium bis(2-methoxyethoxy)aluminumhydride 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 60 wt.% concentration in toluene is commercially available. The reagent can be modified to effect partial reductions.[1]
References
- 1 2 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.
External links
- "Red-Al, Sodium bis(2-methoxyethoxy)aluminumhydride". Organic Chemistry.
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