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Merck

192120

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
UNSPSC Code:
12352112
NACRES:
NA.22
PubChem Substance ID:
24851530
MDL number:
MFCD00013189
Beilstein/REAXYS Number:
3663489

Key Documents

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Product Name

Borane dimethyl sulfide complex solution, 2.0 M in THF

InChI

1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3

SMILES string

B.CSC

InChI key

RMHDLBZYPISZOI-UHFFFAOYSA-N

form

liquid

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

Quality Level

200

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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

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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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

supp_hazards

EUH019

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3603
SHBR5604
SHBQ3319
SHBM8590
SHBK2909

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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)
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
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
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
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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