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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

Quality Level

100

Assay

≥97%

form

powder

mp

284-285 °C (dec.) (lit.)

functional group

nitro

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL9764
MKBX1423V
MKBK1110V
95697KJV
95697KJ

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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)
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
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
B J Johnson
Biochemistry, 20(21), 6103-6108 (1981-10-13)
Highly purified isoaccepting species of transfer ribonucleic acid (tRNA) were prepared by use of a polyacrylamide substituted with nitrobenzeneboronic acid functional groups. This method exploits the well-known ability of boronic acids to complex with RNA cis-diols. tRNA isoacceptors were obtained
K C Usher et al.
Biochemistry, 37(46), 16082-16092 (1998-11-18)
The structures of AmpC beta-lactamase from Escherichia coli, alone and in complex with a transition-state analogue, have been determined by X-ray crystallography. The native enzyme was determined to 2.0 A resolution, and the structure with the transition-state analogue m-aminophenylboronic acid
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