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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:
2938638
MDL number:
MFCD00007193
UNSPSC Code:
12352103
PubChem Substance ID:
24859487
NACRES:
NA.22

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Peter Wipf et al.
Journal of combinatorial chemistry, 4(6), 656-660 (2002-11-12)
A combinatorial library of oxazolines and thiazolines was synthesized in moderate to excellent yields using a newly developed methodology. Free carboxylic acids were directly condensed with amino alcohols and aminothiols in the presence of 3-nitrophenylboronic acid as a dehydration catalyst.
Claire Kaiser et al.
Chemical communications (Cambridge, England), (3)(3), 338-340 (2008-04-11)
Electrokinetic probes based on the differential migration of ternary boronate ester complexes permit the selective analysis of micromolar levels of UV-transparent polyol stereoisomers in urine samples via dynamic complexation-capillary electrophoresis that is applicable to single-step screening of in-born errors of
Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates: synthesis, enzymatic incorporation, and electrochemical detection.
Hana Cahová et al.
Angewandte Chemie (International ed. in English), 47(11), 2059-2062 (2008-02-09)
C W Garner et al.
Biochimica et biophysica acta, 790(1), 91-93 (1984-10-09)
Horse serum cholinesterase (acylcholine acylhydrolase, EC 3.1.1.8) was reversibly inhibited by a variety of alkyl- and areneboronic acids with Ki values ranging from 6.2 mM (methaneboronic acid) to 3.1 microM (diphenylboric acid). Binding to the enzyme was apparently at the
Fan Fei et al.
Analytical and bioanalytical chemistry, 398(3), 1349-1356 (2010-07-29)
The design of boronic acid sensors for photometric detection of carbohydrates has relied on exploiting differences in the thermodynamic stability of complex formation for molecular recognition. Herein, we introduce a direct method for analysis of sugar alcohols using 3-nitrophenylboronic acid
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