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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:
Molecular Weight:
200.02
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Synthesis of 2,6-disubstituted-7,8-dihydro-6H-pyrano[2,3-b]pyrazines
Li, J-C.; et al.
Tetrahedron Letters, 53, 852-853 (2012)
Copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with TMSCF3 and elemental sulfur.
Chao Chen et al.
Angewandte Chemie (International ed. in English), 51(10), 2492-2495 (2012-01-31)
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
Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4'-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)
Semple, G.; et al.
Bioorganic & Medicinal Chemistry, 21, 71-75 (2012)
Yue-Lei Chen et al.
Bioorganic & medicinal chemistry, 20(1), 467-479 (2011-11-22)
C7-Substituted 2-hydroxyisoquinoline-1,3-diones inhibit the strand transfer of HIV integrase (IN) and the reverse-transcriptase-associated ribonuclease H (RNH). Hepatitis C virus (HCV) NS5B polymerase shares a similar active site fold to RNH and IN, suggesting that N-hydroxyimides could be useful inhibitor scaffolds

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