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Sodium bis(2-methoxyethoxy)aluminum hydride acts as a reducing agent in organic synthesis. It is used to prepare azoxyarenes, azoarenes and hydroazoarenes from nitroarenes. It plays an important role for the conversion of aldehydes, ketones, carboxylic acids, esters, acyl halides and anhydrides to primary alcohols. It is also employed in hydroaluminate alkenes and alkynes. It is utilized in the reduction of lactones and epoxides into diols. Further, it serves as a methylation reagent for aryl-activated compounds. In addition to this, it is involved in the reduction of amides, nitriles and amines to the corresponding amines.
Convenient alternative to lithium aluminum hydride for many reductions: Coll. Czech. Chem. Commun., 34, 118 (1969). The reagent is more readily and safely handled, is more stable to air and can be used at high temperatures. For use in the stereospecific reduction of 2-yn-1-ols to (E)-allylic alcohols, and reviews, see: Org. Synth. Coll., 7, 524 (1990):
The reducing properties can be modified by addition of one mole of ethanol, which gives a reagent for the reduction of lactones to lactols, or one mole of N-methylpiperazine or morpholine, which gives a reagent for the high-yield reduction of esters to aldehydes: Synthesis, 526 (1976).
For use as a superior activator/initiator for the formation of Grignard reagents, see: Coll. Czech. Chem. Commun., 38, 1614 (1973).
Xu, J. B.; Cheng, K. J. Studies on the Alkaloids of the Calycanthaceae and Their Syntheses. Molecules 2015, 20 (4), 6715-6738.
Hatano, M.; Yamashita, K.; Mizuno, M.; Ito, O.; Ishihara, K. C-Selective and Diastereoselective Alkyl Addition to beta, gamma-Alkynyl-alpha-imino Esters with Zinc(II)ate Complexes. Angew. Chem. Int. Ed. 2015, 127 (9), 2745-2749.
Gefahrenhinweise (EU): H225-H260-H303-H332-H314-H318-H361-H336-H373-H304
Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. May be harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.
Keep away from any possible contact with water, because of violent reaction and possible flash fire. IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.