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Sodium bis(2-methoxyethoxy)aluminium hydride

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Sodium bis(2-methoxyethoxy)aluminium hydride
Structural formula of red-Al with explicit hydrogens
Names
IUPAC name
Sodium bis(2-methoxyethoxy)aluminumhydride
Other names
Vitride
Identifiers
3D model (JSmol)
Abbreviations SMEAH
ChemSpider
ECHA InfoCard 100.041.056 Edit this at Wikidata
  • InChI=1S/2C3H7O2.Al.Na.2H/c2*1-5-3-2-4;;;;/h2*2-3H2,1H3;;;;/q2*-1;2*+1;; checkY
    Key: XJIQVZMZXHEYOY-UHFFFAOYSA-N checkY
  • [Na+].COCCO[AlH2-]OCCOC
  • [H][Al-](OCCOC)([H])OCCOC.[Na+]
Properties
C6H16AlNaO4
Molar mass 202.161 g·mol−1
Appearance Transparent crystals
Hazards
Occupational safety and health (OHS/OSH):
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).

Red-Al, or sodium bis(2-methoxyethoxy)aluminumhydride, is an organoaluminium compound with the formula NaAlH2(OC2H4OCH3)2. The name which is a trademark of Sigma-Aldrich refers to its being a Reducing aluminium compound. It is used almost exclusively as a solution in toluene, which is used as a reagent in organic synthesis. The compound features tetrahedral aluminium center attached to two hydride and two alkoxides, the latter derived from 2-methoxyethanol.[1]

Some common functional group reductions using Red-Al can be found below:

Red-Al is a potent hydride reducing agent. It converts carboxylic acid anhydrides and lactones to diols. 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.[2]

Comparison with lithium aluminium hydride

As a reagent, Red-Al is comparable with LiAlH4. In contrast with lithium aluminium hydride, Red-Al exhibits good solubility in aromatic solvents. Thus, a 70 wt.%-solution in toluene is commercially available. Its solutions are also more stable to moisture and air than LiAlH4 and more thermally stable, tolerating temperatures up to 200 °C. The reagent can be modified to effect partial reductions.[2]

References

  1. ^ Casensky, B.; Machacek, J.; Abraham, K. (1971). Collection of Czechoslovak Chemical Communications. 36: 2648. {{cite journal}}: Missing or empty |title= (help)CS1 maint: multiple names: authors list (link)
  2. ^ a b 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:10.1002/047084289X.rs049.pub2.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)

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