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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

Pricing and availability is not currently available.

Quality Level

Assay

96%

form

solid

mp

176-180 °C (lit.)

functional group

carboxylic acid
nitro

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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1 of 4

This Item
GF30015582GF60837105GF04638326
manufacturer/tradename

Goodfellow 864-214-83

manufacturer/tradename

Goodfellow 300-155-82

manufacturer/tradename

Goodfellow 608-371-05

manufacturer/tradename

Goodfellow 046-383-26

weight

100 g

weight

250 g

weight

10 g

weight

20 g

max. lump size

10 mm

max. lump size

10 mm

max. lump size

25 mm

max. lump size

25 mm

Application

2,4-Dinitrobenzoic acid can be used as a reactant:
  • In decarboxylative C-N cross-coupling reactions.[1]
  • To synthesize Zwitterionic azaspirocyclic hydantoins by reacting with various carbodiimides via in situ intramolecular dearomatization reaction.[2]
  • To prepare 1-(2,4-dinitrophenyl)ethanone by condensation with dimethyl malonate and subsequent decarboxylation reaction.[3]

It can also be used in the spectrophotometric determination of diazepam in pure samples and in its pharmaceutical preparations.[3] In capillary zone electrophoresis, it can be employed as chromophore probe for the analysis of perfluorinated carboxylic acids in water.[4]

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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    CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
    Sheng W-J, et al.
    Tetrahedron Letters, 56(4), 599-601 (2015)
    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)
    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)

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