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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:
Molecular Weight:
235.10
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

mp

103-107 °C (lit.)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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
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
?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)

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