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Borane-methyl sulfide complex

Borane-methyl sulfide complex Basic information
Product Name:Borane-methyl sulfide complex
Synonyms:Borane diMethyl sulfide coMplex technical, >90% in diMethyl sulfide;Borane diMethyl sulfide coMplex, 1.0 M solution in Methylene chloride, SpcSeal;Borane diMethyl sulfide coMplex, 10.0 M solution in DMS, SpcSeal;Borane diMethyl sulfide coMplex, 2.0 M solution in THF, SpcSeal;Borane diMethyl sulfide coMplex, 2.0 M solution in toluene, SpcSeal;Borane dimethyl sulfide complex solution 1.0 M in methylene chloride;Borane diMethyl sulfide coMplex, 5.0 M solution in diethyl ether, SpcSeal;Trihydro[thiobis[methane]]boron
CAS:13292-87-0
MF:C2H10BS
MW:76.97
EINECS:236-313-6
Product Categories:borane;Synthetic Reagents;B (Classes of Boron Compounds);Boranes;Reduction;Synthetic Organic Chemistry;API intermediates
Mol File:13292-87-0.mol
Borane-methyl sulfide complex Structure
Borane-methyl sulfide complex Chemical Properties
Melting point -40--37°C
Boiling point ~34 °C
density 1.287 g/mL at 25 °C
refractive index 1.4570
Fp 65 °F
storage temp. 2-8°C
solubility Miscible with ethyl ether, tetrahydrofurane, dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene, methylene chloride and other aprotic solvents.
form Solution
color Colorless to pale yellow
Specific Gravity0.801
Water Solubility reacts
Sensitive Air & Moisture Sensitive
BRN 3663489
InChIKeyRMHDLBZYPISZOI-UHFFFAOYSA-N
CAS DataBase Reference13292-87-0(CAS DataBase Reference)
NIST Chemistry ReferenceBorane-methyl sulfide complex(13292-87-0)
EPA Substance Registry SystemBoron, trihydro[thiobis[methane]]-, (T-4)- (13292-87-0)
Safety Information
Hazard Codes F+,Xn,F,Xi
Risk Statements 12-14/15-19-20/22-37/38-41-67-65-63-48/20-38-11-22-14-40-36-21-36/37/38-37
Safety Statements 36/37-62-36/39-33-26-23-16-36-24/25-7/8-43-39-36/37/39
RIDADR UN 3399 4.3/PG 1
WGK Germany 3
RTECS PV5080000
F 10-13-23
TSCA Yes
HazardClass 4.3
PackingGroup II
HS Code 29309090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Borane-methyl sulfide complex Usage And Synthesis
Chemical Propertiesclear colorless to light yellow solution
UsesBorane-dimethyl sulfide complex is used for hydroborations and reductions. Used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones. CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols. Highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.
UsesBorane-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.
General DescriptionBorane 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.
Borane-methyl sulfide complex Preparation Products And Raw materials
Preparation Products4H-AMINO-6-BROMO-2,3-DIHYDROTHIOCHROMEN-1,1-DIOXIDE-->1,1'-DIMETHYLFERROCENE-->4-Hydroxy-6-bromo-2,3-dihydrothiochromen-1,1-dioxide-->5'-BROMO-2'-CHLOROACETOPHENONE-->(S)-5-Hydroxymethyldihydrofuran-2-one-->3-Nitrobenzylammonium hydrochloride-->3-(4-NITRO-PHENYL)-PROPAN-1-OL-->Pinacolborane-->Butylferrocene-->1,1,2-Trimethylpropylborane-->1,1'-DI-N-BUTYLFERROCENE-->BORANE-DIISOPROPYLAMINE-->Ethylferrocene-->Dicyclohexylborane-->1,1'-DIETHYLFERROCENE-->Trimethoxyboroxine-->N-BOC-1-[4-SPIRO-PIPERIDINE]-3-INDANONE
Borane-pyridine complex Hydrogen Sulfide (+)-Diisopinocampheyl chloroborane Methyl Borane-dimethylsulfide tert-Butyl methyl ether N,N-Dimethylformamide Sodium sulfide Borane-methyl sulfide complex ETHANE CARBONYL SULFIDE Tribenuron methyl (2-Methoxyethyl)benzene Dimethyl fumarate Thioanisole CHLOROMETHYL METHYL SULFIDE Dimethyl phthalate Dimethyl sulfate
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