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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:
Molecular Weight:
312.66
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

supp_hazards

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 21, 3731-3731 (1980)
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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