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556327

Sigma-Aldrich

4-Bromophenyl methyl sulfone

97%

Synonym(s):

1-Bromo-4-(methylsulfonyl)benzene

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About This Item

Linear Formula:
BrC6H4SO2CH3
CAS Number:
3466-32-8
Molecular Weight:
235.10
EC Number:
222-421-0
MDL number:
MFCD00025065
UNSPSC Code:
12352100
PubChem Substance ID:
24879546
NACRES:
NA.22

Quality Level

100

assay

97%

mp

103-107 °C (lit.)

functional group

bromo
sulfone

SMILES string

CS(=O)(=O)c1ccc(Br)cc1

InChI

1S/C7H7BrO2S/c1-11(9,10)7-4-2-6(8)3-5-7/h2-5H,1H3

InChI key

FJLFSYRGFJDJMQ-UHFFFAOYSA-N

Application

4-Bromophenyl methyl sulfone may be used to synthesize:
  • biaryl methyl sulfones
  • 5-[[-4-(methylsulfonyl)phenyl]thio]thiophene-2-sulfonamide
  • 1-[4-(methylsulfonyl)phenyl]-1H-pyrazole (Hmsppz)
  • DuP 697 via reaction with (5-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)trimethylsilane

4-Bromophenyl methyl sulfone (1-bromo-4-(methylsulfonyl)benzene) can undergo coupling reaction with benzene sulfonamide in the presence of copper(I)iodide to form the corresponding N-aryl sulfonamide.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV8837
MKCQ1919
MKBX5328V
MKBN9754V
MKBK3627V

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?Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions?
Wang X, et al.
Tetrahedron Letters, 53, 7?10-7?10 (2012)
?Divergent synthesis of 2,3,5-substituted thiophenes by C-H activation/borylation/suzuki coupling?
Kallepalli.AV, et al.
Heterocycles, 80(2), 1429 - 1448 (2010)
Cooperativity and steric hindrance: important factors in the binding of a-cyclodextrin with para-substituted aryl alkyl sulfides, sulfoxides and sulfones.
Davies DM and Deary ME.
J. Chem. Soc. Perkin Trans. II, 7, 1287-1294 (1995)
Carol K Wada et al.
Journal of medicinal chemistry, 45(1), 219-232 (2002-01-05)
A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was
Daniel Tordera et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(26), 8597-8609 (2013-05-08)
A new approach to obtain green-emitting iridium(III) complexes is described. The synthetic approach consists of introducing a methylsulfone electron-withdrawing substituent into a 4-phenylpyrazole cyclometalating ligand in order to stabilize the highest-occupied molecular orbital (HOMO). Six new complexes have been synthesized
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