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461091

Sigma-Aldrich

4-Nitrobenzoic acid

98%

Synonym(s):

p-Nitrobenzoic acid

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About This Item

Linear Formula:
O2NC6H4CO2H
CAS Number:
62-23-7
Molecular Weight:
167.12
Beilstein:
973593
EC Number:
200-526-2
MDL number:
MFCD00007352
UNSPSC Code:
12352100
PubChem Substance ID:
24869806
NACRES:
NA.22

Assay

98%

form

solid

mp

237-240 °C (lit.)

SMILES string

OC(=O)c1ccc(cc1)[N+]([O-])=O

InChI

1S/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)

InChI key

OTLNPYWUJOZPPA-UHFFFAOYSA-N

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General description

4-Nitrobenzoic acid (p-nitrobenzoic acid) is a carboxylic acid derivative. It participates in the biosynthesis of the antibiotic aureothin. Infrared Fourier transform spectroscopic studies suggest that the molecules of 4-nitrobenzoic acid gets adsorbed on the surfaces of fine silver powder as carboxylate.

Application

4-Nitrobenzoic acid may be used in the preparation of compounds (I and III) trans-M2(T(i)PB)2L2, where T(i)PB = 2,4,6-triisopropylbenzoate:
  • compound I (L = 4-nitrobenzoate and M = Mo)
  • compound III (L = 4-nitrobenzoate and M2 = MoW)

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Emmanuel Chanco et al.
Bioorganic & medicinal chemistry, 22(20), 5569-5577 (2014-06-30)
AurF catalyzes the N-oxidation of p-aminobenzoic acid to p-nitrobenzoic acid in the biosynthesis of the antibiotic aureothin. Here we report the characterization of AurF under optimized conditions to explore its potential use in biocatalysis. The pH optimum of the enzyme
Diffuse reflectance infrared spectra of 4-nitrobenzoic acid and 4-cyanobenzoic acid self-assembled on fine silver particles.
Soo H, et al.
Applied Spectroscopy, 52(8) (1998)
Brian G Alberding et al.
Dalton transactions (Cambridge, England : 2003), 43(29), 11397-11403 (2014-06-17)
From the reactions between Mo2(T(i)PB)4, where T(i)PB = 2,4,6-triisopropylbenzoate and two equivalents of the carboxylic acid LH (LH = 4-nitrobenzoic acid and 4'-nitro[1,1'-biphenyl]-4-carboxylic acid) the compounds trans-M2(T(i)PB)2L2 have been prepared: I (L = 4-nitrobenzoate and M = Mo), II (L
Catarina M Quinzii et al.
PloS one, 7(2), e30606-e30606 (2012-02-24)
Coenzyme Q(10) (CoQ(10)) is a potent lipophilic antioxidant in cell membranes and a carrier of electrons in the mitochondrial respiratory chain. We previously characterized the effects of varying severities of CoQ(10) deficiency on ROS production and mitochondrial bioenergetics in cells
Jing He et al.
Journal of the American Chemical Society, 126(12), 3694-3695 (2004-03-25)
The antibiotic aureothin is a rare natural nitroaromatic compound produced by Streptomyces thioluteus. By labeling experiments, we demonstrate for the first time that p-nitrobenzoate (PNBA) serves as a polyketide synthase starter unit. Cloning, heterologous expression, and inactivation experiments reveal that
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