179825
Borane dimethyl sulfide complex
Synonym(s):
(Dimethyl sulfide)trihydroboron, BMS, Borane-dimethyl sulfide
Sign Into View Organizational & Contract Pricing
All Photos(2)
About This Item
Linear Formula:
(CH3)2S · BH3
CAS Number:
Molecular Weight:
75.97
Beilstein:
3663489
EC Number:
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
![9-Borabicyclo[3.3.1]nonane solution 0.5 M in THF](/deepweb/assets/sigmaaldrich/product/structures/180/891/8b64e597-269d-4780-98b6-40889dfd06b9/640/8b64e597-269d-4780-98b6-40889dfd06b9.png)
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
Related Categories
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
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)
Borane Dimethyl Sulfide
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service