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Borane- dimethyl sulfide is used for hydroboration and reduction reactions. It is used in the reduction of aldehydes, ketones, epoxides and carboxylic acids to give corresponding alcohols. It is also involved in the Corey-Itsuno reduction. It acts as an intermediate in the preparation of highly pure semiconductor. It is also employed as a rocket propellant.
Stable, convenient reagent for a wide range of reduction and hydroboration reactions. Reviews: Org. Prep. Proced. Int., 13, 225 (1981); Chem. Rev., 76, 773 (1976); A. Pelter et al, Borane Reagents, Academic Press, N.Y. (1988).
Carboxylic acids are readily reduced to alcohols: J. Org. Chem., 38, 2786 (1973).
Conditions for reduction of amino acids to amino alcohols without racemization are described for L-valine: Org. Synth. Coll., 7, 530 (1990).
By use of refluxing THF as solvent, the reduction can be extended to include esters, primary, secondary and tertiary amides and nitriles: J. Org. Chem., 47, 1389 (1982); Synth. Commun., 21, 1579 (1991).
The selectivity of BMS in reducing free acids more rapidly than esters is reversed in the case of monoesters of malonic acids. The borane binds initially to the acid function, but reduces the ester group intramolecularly: Tetrahedron Lett., 30, 6687 (1989):
For a discussion of the effect of the alkene structure on hydroboration with borane dimethyl sulfide, see: J. Org. Chem., 48, 644 (1983). For cis-anti-Markovnikov hydration of alkenes by hydroboration with BMS, followed by H2O2 oxidation of the borane, see: J. Org. Chem., 39, 1437 (1974).
James, S. N.; Coster, M. J. Synthesis of N-alkylsulfonamides by borane-dimethyl sulfide reduction of N-acylsulfonamides. Tetrahedron Lett. 2015, 56 (16), 2059-2061.
Xie, Z.; Zhou, T.; Gou, Y. Synthesis and characterization of zirconium diboride ceramic precursor. Ceram. Int. 2015, 41 (5), 6226-6231.
Mentions de danger (UE): H225-H260-H300-H314-H318-H335
Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. Fatal if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May cause respiratory irritation.
Mentions de prudence: P223-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
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.