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Merck
CN

325104

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

Key Documents

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Product Name

3-Nitrophenylboronic acid, ≥97%

InChI

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

SMILES string

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

InChI key

ZNRGSYUVFVNSAW-UHFFFAOYSA-N

assay

≥97%

form

powder

mp

284-285 °C (dec.) (lit.)

functional group

nitro

Quality Level

100

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Application

Catalyzes ene carbocyclization of acetylenic dicarbonyl compounds
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

Other Notes

Contains varying amounts of anhydride

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL9764
MKBX1423V
MKBK1110V
95697KJV
95697KJ

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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
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
Malcolm P Nicholls et al.
Organic & biomolecular chemistry, 2(10), 1434-1441 (2004-05-12)
The structures of thermodynamically stable aromatic boronic acid : cyclic carbohydrate chelates in aqueous alkaline media have been studied using 1H NMR spectroscopy and molecular modelling. It is found that interacting saccharides must necessarily possess a synperiplanar diol functionality for
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
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