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.
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Applications
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.
Solubility
Miscible with ethyl ether, dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene, methylene chloride and other aprotic solvents.
Notes
Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Store in a cool place. Incompatible with acids, water, alcohols, bromine, acid anhydrides, acid chlorides and oxidizing agents.
RUO – Research Use Only
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.