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325104

Sigma-Aldrich

3-Nitrophenylboronic acid

≥97%

Synonym(s):

3-Nitrobenzeneboronic acid, m-Nitrobenzeneboronic acid, m-Nitrophenylboronic acid, NSC 401539, NSC 59739

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About This Item

Linear Formula:
O2NC6H4B(OH)2
CAS Number:
13331-27-6
Molecular Weight:
166.93
Beilstein/REAXYS Number:
2938638
MDL number:
MFCD00007193
UNSPSC Code:
12352103
PubChem Substance ID:
24859487
NACRES:
NA.22

Quality Level

100

assay

≥97%

form

powder

mp

284-285 °C (dec.) (lit.)

SMILES string

OB(O)c1cccc(c1)[N+]([O-])=O

InChI

1S/C6H6BNO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-10H

InChI key

ZNRGSYUVFVNSAW-UHFFFAOYSA-N

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Application

Reactant involved in:
  • Copper-catalyzed arylation
  • Palladium-catalyzed decarboxylative coupling
  • Suzuki-Miyaura cross-coupling
  • Oxidative carbocyclization / arylation
  • Addition to arylpropargyl alcohols

Additionally used as a reactant for synthesizing biologically active molecules such as:
  • Inhibitors of angiogenesis
  • Biaryl-olefins with antiproliferative activities
Catalyzes ene carbocyclization of acetylenic dicarbonyl compounds

Other Notes

Contains varying amounts of anhydride

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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The discovery and development of an efficient ene carbocyclization of 1,3-dicarbonyl compounds bearing pendent terminal alkyne substituents under 3-nitrobenzeneboronic acid catalysis is described. The reaction is efficient, easy to perform and general to a wide range of ketoester substrates.
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