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179825

Sigma-Aldrich

Borane dimethyl sulfide complex

Synonym(s):

(Dimethyl sulfide)trihydroboron, BMS, Borane-dimethyl sulfide

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About This Item

Linear Formula:
(CH3)2S · BH3
CAS Number:
13292-87-0
Molecular Weight:
75.97
Beilstein:
3663489
EC Number:
236-313-6
MDL number:
MFCD00013189
UNSPSC Code:
12352112
PubChem Substance ID:
24850657
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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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.
View returnable container options.

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

Signal Word

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 Code

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

WGK

WGK 1

Flash Point(F)

64.4 °F

Flash Point(C)

18 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Borane Dimethyl Sulfide
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Highly Enantioselective Borane Reduction of Prochiral Ketones Catalyzed by C3-Symmetric Tripodal β-Hydroxy Amides
Fang, Tao and Xu, Jiaxi and Du, Da-Ming
Synlett, 2006(10), 1559-1563 (2006)
Highly catalytic enantioselective reduction of aromatic ketones using chiral polymer-supported Corey, Bakshi, and Shibata catalysts
Degni S, et al.
Tetrahedron Asymmetry, 15, 1495-1499 (2004)
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