179825
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:
Molecular Weight:
75.97
UNSPSC Code:
12352112
NACRES:
NA.22
PubChem Substance ID:
EC Number:
236-313-6
Beilstein/REAXYS Number:
3663489
MDL number:
Quality Level
form
liquid
reaction suitability
reagent type: reductant
density
0.801 g/mL at 25 °C (lit.)
functional group
thioether
storage temp.
2-8°C
SMILES string
B.CSC
InChI
1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3
InChI key
RMHDLBZYPISZOI-UHFFFAOYSA-N
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
Storage Class
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
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Classifications
Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Water-react. 1
Regulatory Information
危险化学品
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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 179825-100ML | 04061838754479 |
| 179825-18L-C | 04061838230751 |
| 179825-4X25ML | 04061838754493 |
| 179825-25ML | 04061838754486 |
| 179825-800ML | 04061838754509 |