179825

Borane dimethyl sulfide complex

• Synonym(s): (Dimethyl sulfide)trihydroboron, BMS, Borane-dimethyl sulfide
• Linear Formula: (CH₃)₂S · BH₃
• CAS Number: 13292-87-0
• Molecular Weight: 75.97
• Beilstein/REAXYS Number: 3663489
• EC Number: 236-313-6
• MDL number: MFCD00013189
• UNSPSC Code: 12352112
• PubChem Substance ID: 24850657
• NACRES: NA.22

Properties

• 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

Description

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

Safety Information

• pictograms: GHS02,GHS06,GHS08,GHS05
• signalword: Danger
• hcodes: H225,H260,H301 + H311,H318,H360FD,H412
• pcodes: P210 - P231 + P232 - P273 - P280 - P301 + P310 - P305 + P351 + P338
• 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