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Sigma-Aldrich

Boron tribromide dimethyl sulfide complex

97%

Synonym(s):

Dimethyl sulfide-tribromoborane, Tribromoborane-methyl sulfide

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About This Item

Linear Formula:
BBr3 · S(CH3)2
CAS Number:
29957-59-3
Molecular Weight:
312.66
MDL number:
MFCD00043296
UNSPSC Code:
12352101
PubChem Substance ID:
24854865
NACRES:
NA.22
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Assay

97%

form

powder

mp

106-108 °C (lit.)

functional group

thioether

SMILES string

C[S+](C)[B-](Br)(Br)Br

InChI

1S/C2H6BBr3S/c1-7(2)3(4,5)6/h1-2H3

InChI key

NCVLHAUANAMSTL-UHFFFAOYSA-N

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Application

Boron tribromide dimethyl sulfide complex (BBr3S(CH3)2) can be used as a reagent:
  • To deprotect the methylenedioxy acetal bonding of poly vinyl-1, 3-benzodioxole.[1]
  • To prepare benzyl S,S′-diphenyl acetal by reacting with carboxylic acid and thexylphenylthioborane.[2]
  • To prepare Baylis-Hillman adducts by the reaction of aldehydes with 3-buten-2-one.[3]

Boron tribromide in convenient solid form. Used as a brominating agent.[4]
Reactant for preparation of:
  • Precursor of HIV protease inhibitor KNI 764 using cation-exchange resin mediated Mannich reaction

Reagent for:
  • Baylis-Hillman reactions

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN5016
SHBL7012
SHBL4601
SHBK8616
SHBK5305

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Inorganic Chemistry, 29, 4162-4162 (1990)
Protection and Polymerization of Functional Monomers. 24. Anionic Living Polymerizations of 5-Vinyl-and 4-Vinyl-1, 3-benzodioxoles
Ishizone T, et al.
Macromolecules, 28(11), 3787-3793 (1995)
Dimethyl sulfide-boron trihalide-mediated reactions of α, β, unsaturated ketones with aldehydes: one-pot synthesis of Baylis-Hillman adducts and ?-halomethyl enones
Iwamura T, et al.
Tetrahedron, 57(40), 8455-8462 (2001)
Direct conversion of carboxylic acids and carboxylic esters into S, S?-diphenyl acetals and phenyl sulfides with thexylphenylthioborane
Kim S and Kim SS
Tetrahedron Letters, 28(17), 1913-1916 (1987)

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