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675903

Sigma-Aldrich

4-(Methanesulfonyl)phenylboronic acid

≥95.0%

Synonym(s):

4-(Methanesulfonyl)benzeneboronic acid, 4-(Methylsulfonyl)phenylboronic acid, 4-Methansulfonylphenylboronic acid

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About This Item

Linear Formula:
(H3CSO2)C6H4B(OH)2
CAS Number:
149104-88-1
Molecular Weight:
200.02
MDL number:
MFCD01630820
UNSPSC Code:
12352103
PubChem Substance ID:
24885307
NACRES:
NA.22

Quality Level

100

assay

≥95.0%

form

solid

mp

289-293 °C

SMILES string

CS(=O)(=O)c1ccc(cc1)B(O)O

InChI

1S/C7H9BO4S/c1-13(11,12)7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3

InChI key

VDUKDQTYMWUSAC-UHFFFAOYSA-N

Related Categories

General description

Contains varying amounts of anhydride

Application

4-(Methanesulfonyl)phenylboronic acid may be used as reagent for:
  • sequential Suzuki cross-coupling reactions
  • Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids
  • directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles
  • Barton-Zard pyrrole cyclocondensations and Baeyer-Villiger oxidations
  • diplar cycloaddition and palladium-catalyzed cross-coupling processes
  • continuous flow Suzuki reactions for odanacatib intermediate synthesis


Reagent used in Preparation of
  • diarylaminopyridines as potential anti-malarial agents
  • hydropyranopyrazine via chloropyrazinecarboxaldehyde and olefination
  • biaryl sulfone derivatives as antagonists of the histamine H3 receptor
  • novel kinase inhibitor scaffolds with potential antitumor effects
  • Hepatitis C virus inhibition activity of N-hydroxyisoquinoline di
Highly effective boronic acid used in a rhodium-catalyzed asymmetric 1,4-addition to 4-oxobutenamides.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Jamie L Zigterman et al.
The Journal of organic chemistry, 72(23), 8870-8876 (2007-10-12)
A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to >99:1, >96% ee) and moderate to excellent yields (54-99%). The key to high selectivity is the use of sterically
Combined batch and continuous flow procedure to the chemo-enzymatic synthesis of biaryl moiety of Odanacatib.
de Oliveira Lopes R, et al.
Journal of Molecular Catalysis. B, Enzymatic, 104, 101-107 (2014)
Pamela Kassis et al.
European journal of medicinal chemistry, 46(11), 5416-5434 (2011-09-29)
We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were used to generate several substitutions of the pyridine and pyrazine rings. The synthesis included Stille or
Optimization of a novel kinase inhibitor scaffold for the dual inhibition of JAK2 and FAK kinases
Zificsak, C. A.; et al.
Bioorganic & Medicinal Chemistry, 22, 133-137 (2012)
Facile Access to 3,5-Dihalogenated Pyrazoles by Sydnone Cycloaddition and their Versatile Functionalization by Pd-Catalyzed Cross-Coupling Processes
Delaunay, T.; et al.
European Journal of Medicinal Chemistry, 20-21, 3837-3848 (2011)
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