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247383

Sigma-Aldrich

Boron tribromide dimethyl sulfide complex solution

1.0 M in methylene chloride

Synonym(s):

Dimethyl sulfide-tribromoborane, Tribromoborane-methyl sulfide

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About This Item

Linear Formula:
(CH3)2S·BBr3
CAS Number:
29957-59-3
Molecular Weight:
312.66
MDL number:
MFCD00043296
UNSPSC Code:
12352101
PubChem Substance ID:
24854866
NACRES:
NA.22

form

liquid

Quality Level

100

concentration

1.0 M in methylene chloride

density

1.456 g/mL at 25 °C

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

Application

Boron tribromide dimethyl sulfide complex (BBr3S(CH3)2) can be used as a reagent:
  • To prepare demethylated products from aryl methyl ethers by deprotection of methyl groups.
  • To hydrolyze 1,3-methylenedioxole ring compounds to 1,2-dihydroxy compounds.
  • To prepare benzyl S,S′-diphenyl acetal by reacting with phenylacetic acid and thexylphenylthioborane.
  • To synthesize Baylis−Hillman adducts and α-halomethyl enones by the reaction between aldehydes and 3-buten-2-one.

Reactant for preparation of:
  • Precursor of HIV protease inhibitor KNI 764 using cation-exchange resin mediated Mannich reaction

Reagent for:
  • Baylis-Hillman reactions

Signal Word

Danger

Hazard Statements

H314,H336,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Boron trihalide-methyl sulfide complexes as convenient reagents for dealkylation of aryl ethers
Williard PG and Fryhle CB
Tetrahedron Letters, 21(39), 3731-3734 (1980)
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)
Tetrahedron Letters, 21, 3731-3731 (1980)

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