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137952

Sigma-Aldrich

2,4-Dinitrobenzoic acid

96%

Synonym(s):

1-Carboxy-2,4-dinitrobenzene

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About This Item

Linear Formula:
(O2N)2C6H3CO2H
CAS Number:
Molecular Weight:
212.12
Beilstein:
658650
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

form

solid

mp

176-180 °C (lit.)

SMILES string

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

InChI

1S/C7H4N2O6/c10-7(11)5-2-1-4(8(12)13)3-6(5)9(14)15/h1-3H,(H,10,11)

InChI key

ZIIGSRYPZWDGBT-UHFFFAOYSA-N

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Application

2,4-Dinitrobenzoic acid can be used as a reactant:
  • In decarboxylative C-N cross-coupling reactions.
  • To synthesize Zwitterionic azaspirocyclic hydantoins by reacting with various carbodiimides via in situ intramolecular dearomatization reaction.
  • To prepare 1-(2,4-dinitrophenyl)ethanone by condensation with dimethyl malonate and subsequent decarboxylation reaction.

It can also be used in the spectrophotometric determination of diazepam in pure samples and in its pharmaceutical preparations. In capillary zone electrophoresis, it can be employed as chromophore probe for the analysis of perfluorinated carboxylic acids in water.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

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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Lena Wójcik et al.
Journal of chromatography. A, 1128(1-2), 290-297 (2006-07-14)
Perfluorinated carboxylic acids (PFCAs) belong to anthropogenic fluoroorganic compounds that have been detected in the natural environment and living organisms including humans. A capillary zone electrophoretic method with indirect UV detection using 2,4-dinitrobenzoic acid (2,4-DNBA) as a chromophore probe has
W F El-Hawary et al.
International journal of biomedical science : IJBS, 3(1), 50-55 (2007-03-01)
The interaction of diazepam with picric acid (I), 3,5-dinitrobenzoic acid (II) and 2,4-dinitrobenzoic acid (III) was found to be useful for its spectrophotometric determination. The quantitation was carried out at 475, 500, and 500 nm for the reaction with (I)
Photolysis of dinitrobenzyl alcohols, dinitrobenzaldehydes, and nitrobenzoic acids in seawater, estuary water, and pure water.
Prak DJL, et al.
Marine Chemistry, 145-147, 29-36 (2012)
Spectrophotometric determination of diazepam in pure form, tablets and ampoules
El-Hawary WF, et al.
International Journal of Biomedical Science : IJBS, 3(1), 50-50 (2007)
Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity
Jeanguenat A, et al.
Bioorganic & Medicinal Chemistry, 24(3), 403-427 (2016)

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