192120

Borane dimethyl sulfide complex solution

2.0 M in THF

• Synonym(s): BMS, Trihydro[thiobis[methane]]boron
• Linear Formula: (CH₃)₂S · BH₃
• CAS Number: 13292-87-0
• Molecular Weight: 75.97
• Beilstein/REAXYS Number: 3663489
• MDL number: MFCD00013189
• UNSPSC Code: 12352112
• PubChem Substance ID: 24851530
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• reaction suitability: reagent type: reductant
• concentration: 2.0 M in THF
• density: 0.855 g/mL at 25 °C
• 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) acts as a highly efficient and selective reducing agent in the presence of catalytic sodium tetrahydroborate for α-hydroxy esters. Asymmetric borane reduction of a variety of prochiral ketones with BMS using spiroborate esters as catalyst has been reported.

Application

Borane dimethyl sulfide complex (BMS) solution may be used in the following studies:

• One-pot conversion of alkynes into 1,2-diols.
• Preparation of iminopentitols.
• Reduction of representative organic functional groups, such as esters, nitriles and amides.
• Used along with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.
• Asymmetric reduction of ferrocenyl-1,3-diketones to chiral 1,3-diols.
• Highly enantioselective reduction of ketones catalyzed by C₃-symmetric tripodal hydroxyamides.

Reactant used as a regioselective reducing agent

Reactant involved in:

• Hydroboration / oxidation

Synthesis of cage compounds

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H260,H302 + H312,H318,H335,H336,H351,H360FD
• pcodes: P210 - P231 + P232 - P280 - P303 + P361 + P353 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - STOT SE 3 - Water-react 1
• target_organs: Respiratory system
• supp_hazards: EUH019
• Storage Class: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• wgk_germany: WGK 1
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter