Borane Dimethylsulfide

Other Names:

Borane-dimethyl sulfide complex

Dimethyl sulfide borane

(Dimethyl sulfide)trihydroboron

BMS

General Information:

Structure:

CAS Number: 13292-87-0

Molecular Weight: 75.96 g/mol

Appearance: Colorless liquid

Melting Point: -38 C

Density: 0.801 g/mL at 25 C

Borane dimethylsulfide (BMS) is a complex of borane with dimethylsulfide. The other common complex of borane is borane-THF. BMS is more stable than borane-THF and is therefore available in higher concentrations. BMS has the drawback of being smelly due to its dimethylsulfide content.

Common Uses:

Reagent for the reduction of carboxylic acids to alcohols

Procedure excerpt:

To a solution of the SM (1.0 g, 6.4 mmol) in THF (18 mL) at 0 C was added BH3-SMe2 (6.4 mL, 12.8 mmol). The reaction mixture was stirred at 0 C for 2 h, then RT for 3 h. . . .

[full procedure]

Reagent for the reduction of esters to alcohols

Procedure excerpt:

To a solution of the SM (137 g, 0.34 mol) in THF (1.3 L) at 0 C was slowly added BH3-SMe2 (97 mL, 1.02 mol). The reaction mixture was allowed to warm to RT then . . .

[full procedure]

Reagent for the reduction of nitriles to amines

Procedure excerpt:

To a solution of the SM (117.5 g, 519.8 mmol) in dry THF under argon was slowly added BH3-SMe2 (68 mL, 675.7 mmol) over 30 min via dropping funnel. The reaction . . .

[full procedure]

Safety:

Borane dimethylsulfide (BMS) is a flammable liquid.

References:

1) Patent Reference: WO2011061214, page 87, (8.2 MB)

2) Patent Reference: WO2012069948, page 55, (3.9 MB)

3) UK Pat App GB 1463151A, page 132

4) Wikipedia: Borane dimethylsulfide (link)

5) www.alfa.com: L07705 Borane-dimethyl sulfide complex, 94% (link)

6) www.tcichemicals.com: Dimethyl Sulfide Borane (link)

7) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents