325104
3-Nitrophenylboronic acid
≥97%
Synonym(s):
3-Nitrobenzeneboronic acid, m-Nitrobenzeneboronic acid, m-Nitrophenylboronic acid, NSC 401539, NSC 59739
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All Photos(3)
About This Item
Linear Formula:
O2NC6H4B(OH)2
CAS Number:
Molecular Weight:
166.93
Beilstein:
2938638
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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:
Additionally used as a reactant for synthesizing biologically active molecules such as:
- 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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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
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
R E Feeney et al.
Journal of protein chemistry, 10(2), 167-170 (1991-04-01)
The activity of antifreeze glycoprotein from the blood serum of Boreagadus saida was strongly inhibited by ions of organic boronic acids as well as by borate. The activity of nonglycoprotein from the blood serum of Pseudopleuronectus americanus, however, was not
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