Borane dimethylsulfide

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Borane dimethylsulfide
Names
Other names
BMS, Borane-dimethyl sulfide
Identifiers
3D model (
JSmol
)
ECHA InfoCard
 100.032.998 Edit this at Wikidata
EC Number
  • 236-313-6
UNII
  • InChI=1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3
    Key: RMHDLBZYPISZOI-UHFFFAOYSA-N
  • [BH3-][S+](C)C
Properties
BH3·S(CH3)2
Molar mass 75.96 g/mol
Appearance colorless liquid
Density 0.801 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Borane dimethylsulfide (BMS) is a

aprotic solvents
.

Preparation and structure

Although usually purchased, BMS can be prepared by absorbing diborane into dimethyl sulfide:[3]

B2H6 + 2 S(CH3)2 → 2 BH3·S(CH3)2

It can be purified by bulb to bulb vacuum transfer. Although a structure of BMS has not been determined crystallographically, (pentafluorophenyl)-borane dimethylsulfide (C6F5BH2·S(CH3)2), has been examined by X-ray crystallography.[4] The boron atom adopts a tetrahedral molecular geometry.

Reactions

Hydroborations

Due to the experimental ease of its use, BMS has become common in

alkynes to the corresponding cis-alkenes
.

Reductions

BMS has been employed for the

Acid chlorides
are not reduced by BMS.

Borane dimethylsulfide is one of the most common bulk reducing agents used in the

THF, however its increased stability in the presence of moisture and oxygen makes it the reagent of choice for the reduction.[6]

Safety

Borane dimethylsulfide is flammable and reacts readily with water to produce a flammable gas. It also has an unpleasant smell.[7]

References

  1. doi:10.1080/00304948109356130
    .
  2. ^
    doi:10.1021/ja01467a056
    .
  3. doi:10.1021/jo00815a047
    .
  4. doi:10.1021/om100152v
    .
  5. ^ Atsushi Abiko (1925). "Dicyclohexylboron Trifluoromethylsulfonate". Organic Syntheses. 79: 103; Collected Volumes, vol. 10, p. 273.
  6. PMID 29711061
    .
  7. ^ "Sigma-Aldrich Material Safety Data Sheet". www.sigmaaldrich.com/. Retrieved 29 November 2014.
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