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179825

Sigma-Aldrich

Borane dimethyl sulfide complex

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Synonym(s):
(Dimethyl sulfide)trihydroboron, BMS, Borane-dimethyl sulfide
Linear Formula:
(CH3)2S · BH3
CAS Number:
Molecular Weight:
75.97
Beilstein/REAXYS Number:
3663489
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: reductant

density

0.801 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

B.CSC

InChI

1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3

InChI key

RMHDLBZYPISZOI-UHFFFAOYSA-N

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vibrant-m

179825

Borane dimethyl sulfide complex

density

0.801 g/mL at 25 °C (lit.)

density

0.855 g/mL at 25 °C

density

-

density

1.347 g/mL at 25 °C

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

form

liquid

form

liquid

form

solid

form

liquid

General description

Borane dimethyl sulfide complex (BMS) is a commonly used reagent and a mediator for hydroboration reaction for the preparation of organoborane compounds, which are utilized as key intermediates in organic synthesis. BMS is also employed as a reducing agent for the reduction of various functional groups such as aldehydes, ketones, epoxides, esters, and carboxylic acids to corresponding alcohols.

Application

Borane-dimethyl sulfide (BH3 Me2S) can be used as a reagent:
  • For the selective synthesis of 1,3,5-oxygenated compounds from dimethyl 3-oxoglutarate.
  • For the conversion of ozonides to alcohols.
  • In the CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols.
  • For enantioselective reduction of ketones to chiral secondary alcohols in the presence of C3-symmetric tripodal hydroxyamide as a ligand.
  • For the hydroboration reduction and other applications.
  • With a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.

Packaging

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Other Notes

10.0-10.2 M as BH3. May contain excess methyl sulfide.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Water-react 1

Storage Class

4.3 - Hazardous materials, which set free flammable gases upon contact with water

wgk_germany

WGK 1

flash_point_f

64.4 °F

flash_point_c

18 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Customers Also Viewed

Generation of bis (pentafluorophenyl) borane-dimethyl sulfide complex as a solution of hexane and its application to hydroboration of alk-1-yne with pinacolborane
Hoshi M, et al.
Tetrahedron Letters, 48(48), 8475-8478 (2007)
A convenient method for the reduction of ozonides to alcohols with borane-dimethyl sulfide complex
Flippin LA, et al.
The Journal of Organic Chemistry, 54(6), 1430-1432 (1989)
Efficient synthesis of 1, 3, 5-oxygenated synthons from dimethyl 3-oxoglutarate: first use of borane-dimethyl sulfide complex as a regioselective reducing agent of 3-oxygenated glutarate derivatives
Riatto VB, et al.
Journal of the Brazilian Chemical Society, 22(1), 172-175 (2011)
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Study of Hydroboration of (μ-H)2Os3(CO)10 with Various Borane Complexes(BH3?L: L=Lewis base)
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J. Korean Chem. Soc., 47, 675-678 (2003)

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