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192120

Sigma-Aldrich

Borane dimethyl sulfide complex solution

2.0 M in THF

Synonym(s):

BMS, Trihydro[thiobis[methane]]boron

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About This Item

Linear Formula:
(CH3)2S · BH3
CAS Number:
13292-87-0
Molecular Weight:
75.97
Beilstein:
3663489
MDL number:
MFCD00013189
UNSPSC Code:
12352112
PubChem Substance ID:
24851530
NACRES:
NA.22

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

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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

Signal Word

Danger

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

Supplementary Hazards

EUH019

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 1

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Metal hydrides
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

192120-BULK:
192120-800ML:4548173112367
192120-VAR:
192120-4X25ML:
192120-PZ:
192120-8L:4548173112374
192120-100ML:4548173112350
192120-20L:
192120-18L:4548173250281

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR5604
SHBQ3319
SHBM8590
SHBK2909
STBH6310

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Ana M Gómez et al.
Organic letters, 4(3), 383-386 (2002-02-01)
Primary ozonides derived from alkenyl stannanes display an unusual stability and can be transformed into 1,2-diols by treatment with dimethyl sulfide and borane-methyl sulfide complex. This observation has been incorporated into the development of a novel one-pot strategy for the
M Godskesen et al.
Bioorganic & medicinal chemistry, 4(11), 1857-1865 (1996-11-01)
The four stereoisomeric 1,5-dideoxy-1,5-iminopentitols with D-arabino-(D-lyxo-) (3), ribo- (9), L-lyxo (L-arabino-) (13) and xylo-(18) configurations were synthesized. The corresponding aldonolactones (1, 7 and 11) or aldonic acid ester (15b) having a leaving group at C-5 gave by reaction with aqueous
Viatcheslav Stepanenko et al.
Tetrahedron letters, 48(33), 5799-5802 (2007-08-13)
Novel spiroborate esters derived nonracemic 1,2-aminoalcohols and ethylene glycol are reported as highly effective catalysts for the asymmetric borane reduction of a variety of prochiral ketones with borane-dimethyl sulfide complex at room temperature. Optically active alcohols were obtained in excellent
Selective reductions. 29. A simple technique to achieve an enhanced rate of reduction of representative organic compounds by borane-dimethyl sulfide.
Brown HC, et al.
The Journal of Organic Chemistry, 47(16), 3153-3163 (1982)
Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
Wang G, et al.
Tetrahedron Asymmetry, 17, 2074-2074 (2006)
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