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675903

Sigma-Aldrich

4-(Methanesulfonyl)phenylboronic acid

≥95.0%

Synonyme(s) :

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

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About This Item

Formule linéaire :
(H3CSO2)C6H4B(OH)2
Numéro CAS:
149104-88-1
Poids moléculaire :
200.02
Numéro MDL:
MFCD01630820
Code UNSPSC :
12352103
ID de substance PubChem :
24885307
Nomenclature NACRES :
NA.22

Pureté

≥95.0%

Forme

solid

Pf

289-293 °C

Chaîne SMILES 

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

Clé InChI

VDUKDQTYMWUSAC-UHFFFAOYSA-N

Catégories apparentées

Description générale

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Jessica G Greger et al.
The Journal of organic chemistry, 76(20), 8203-8214 (2011-09-15)
A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry
Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS
Tetrahedron Letters, 53, 166-169 (2012)
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
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