RED-AL OR SODIUM BIS(2-METHOXYETHOXY)ALUMINUMHYDRIDE[NaAlH2(OCH2CH2OCH3)2]

·         CAS Number 22722-98-1

·         Linear Formula NaAlH₂(OCH₂CH₂OCH₃)₂

·         Molecular Weight 202.16

·          MDL number MFCD00011631

·          PubChem Substance ID 24851740

Sodium bis(2-methoxyethoxy)aluminumhydride (trade names Red-Al, Synhydrid, Vitride) is an organoaluminium compound with the formula NaAlH₂(OCH₂CH₂OCH₃)₂. 

Detailed description

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 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.

Red-Al 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. 

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