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HomeProduct name listBorane-methyl sulfide complex

Borane-methyl sulfide complex

Synonym(s):(Dimethyl sulfide)trihydroboron;BMS;Borane-dimethyl sulfide;Trihydro[thiobis[methane]]boron

  • CAS NO.:13292-87-0
  • Empirical Formula: C2H10BS
  • Molecular Weight: 76.97
  • MDL number: MFCD00013189
  • EINECS: 236-313-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Borane-methyl sulfide complex Structural

What is Borane-methyl sulfide complex?

Description

Borane dimethylsulfide (BMS) is a complex of borane with dimethylsulfide. The other common complex of borane is borane-THF. BMS is more stable than borane-THF and is therefore available in higher concentrations. BMS has the drawback of being smelly due to its dimethylsulfide content.

Chemical properties

clear colorless to light yellow solution

The Uses of Borane-methyl sulfide complex

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.

The Uses of Borane-methyl sulfide complex

Borane-methyl sulfide complex
To a solution of the SM (1.0 g, 6.4 mmol) in THF (18 mL) at 0 C was added BH3-SMe2 (6.4 mL, 12.8 mmol). The reaction mixture was stirred at 0 C for 2 h, then RT for 3 h. The mixture was cooled to 0 C and quenched with sat aq K2CO3 (5 mL). The layers were separated and the aq layer was extracted with EtOAc (2 x 15 mL) and diethyl ether (2 x 15 mL). The combined org layers were dried (Na2SO4) and concentrated to provide the product as a colorless oil. [1.0 g, 100 %]

The Uses of Borane-methyl sulfide complex

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.

What are the applications of Application

Borane dimethyl sulfide complex is a convenient and stable source of borane

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.

Properties of Borane-methyl sulfide complex

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.
appearance Colorless liquid
form  Solution
color  Colorless to pale yellow
Specific Gravity 0.801
Water Solubility  reacts
Sensitive  Air & Moisture Sensitive
BRN  3663489
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)

Safety information for Borane-methyl sulfide complex

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H260:Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases
H318:Serious eye damage/eye irritation
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P231+P232:Handle under inert gas. Protect from moisture.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Borane-methyl sulfide complex

InChIKey RMHDLBZYPISZOI-UHFFFAOYSA-N

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