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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:
610-30-0
Molecular Weight:
212.12
Beilstein/REAXYS Number:
658650
EC Number:
210-219-5
MDL number:
MFCD00017006
UNSPSC Code:
12352100
PubChem Substance ID:
24848224
NACRES:
NA.22

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
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Zwitterionic Azaspirocyclic Hydantoins
S Culf A, et al.
Letters in Organic Chemistry, 13(8), 566-571 (2016)
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)
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)
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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