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Borane-methyl sulfide complex

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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
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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
Flash point:
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
Specific Gravity
0.801
color 
Colorless to pale yellow
Water Solubility 
reacts
Sensitive 
Air & Moisture Sensitive
BRN 
3663489
InChIKey
RMHDLBZYPISZOI-UHFFFAOYSA-N
CAS DataBase Reference
13292-87-0(CAS DataBase Reference)
NIST Chemistry Reference
Borane-methyl sulfide complex(13292-87-0)
EPA Substance Registry System
Boron, trihydro[thiobis[methane]]-, (T-4)- (13292-87-0)
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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
10-13-23
TSCA 
Yes
HazardClass 
4.3
PackingGroup 
II
HS Code 
29309090

MSDS

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Borane-methyl sulfide complex Usage And Synthesis

Chemical Properties

clear colorless to light yellow solution

Uses

Borane-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.

Uses

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.

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.

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