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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

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 Code

11 - Combustible Solids

WGK

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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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
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)
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)
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
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