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Sigma-Aldrich

Borane dimethyl sulfide complex

Sinónimos:

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

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About This Item

Fórmula lineal:
(CH3)2S · BH3
Número de CAS:
13292-87-0
Peso molecular:
75.97
Beilstein/REAXYS Number:
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

Categorías relacionadas

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

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
Study of Hydroboration of (μ-H)2Os3(CO)10 with Various Borane Complexes(BH3?L: L=Lewis base)
Chung JH
J. Korean Chem. Soc., 47, 675-678 (2003)
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)
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)
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