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13292-87-0 - Borane-dimethyl sulfide complex, 94% - BMS - Borane-methyl sulfide - L07705 - Alfa Aesar

L07705 Borane-dimethyl sulfide complex, 94%

CAS Number
Borane-methyl sulfide

Size Price ($) Quantity Availability
25ml 47.97
100ml 120.51
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Borane-dimethyl sulfide complex, 94%


Chemical Properties

Formula Weight
Melting point
Boiling Point
ca 44° dec.
Flash Point
Refractive Index
Air & Moisture Sensitive
Miscible with ethyl ether, dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene, methylene chloride and other aprotic solvents.


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.


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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H260-H300-H335-H314-H318

Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. Fatal if swallowed. May cause respiratory irritation. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P231+P232-P260-P261-P301+P310-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

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