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108898

Sigma-Aldrich

4-Nitro-o-phenylenediamine

98%

Synonym(s):

1,2-Diamino-4-nitrobenzene

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About This Item

Linear Formula:
O2NC6H3(NH2)2
CAS Number:
99-56-9
Molecular Weight:
153.14
Beilstein/REAXYS Number:
608106
EC Number:
202-766-3
MDL number:
MFCD00007724
UNSPSC Code:
12352100
eCl@ss:
39030501
PubChem Substance ID:
24846835
NACRES:
NA.22

Quality Level

100

assay

98%

mp

199-201 °C (lit.)

solubility

1 N HCl: ethanol, 1:1: soluble 50 mg/mL

SMILES string

Nc1ccc(cc1N)[N+]([O-])=O

InChI

1S/C6H7N3O2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H,7-8H2

InChI key

RAUWPNXIALNKQM-UHFFFAOYSA-N

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Application

4-Nitro-o-phenylenediamine was used to study the in vitro activation of 4-nitro-o-phenylenediamine into a potent mutagen in Salmonella typhimurium strain TA98 .

Biochem/physiol Actions

4-Nitro-o-phenylenediamine is a direct-acting mutagen.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

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, Faceshields, 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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S J Toering et al.
Mutation research, 361(2-3), 81-87 (1996-12-12)
Aromatic amines are activated into mutagens by both animal and plant systems. For plant-activated aromatic amines an important step in this process involves peroxidase enzymes. 4-nitro-o-phenylenediamine (NOP) is a well known direct-acting mutagen that can be enhanced in mutagenic potency
K Kaur et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 40(10), 1475-1482 (2002-10-22)
The antimutagenic effect of benzene, chloroform, acetone and methanol fractions from Terminalia arjuna, a well-known medicinal plant, was determined against Acid Black dye, 2-aminofluorene (2AF) and 4-nitro-o-phenylenediamine (NPD) in TA98 Frameshift mutagen tester strain of Salmonella typhimurium. Among the different
E A Varanda et al.
Teratogenesis, carcinogenesis, and mutagenesis, 19(6), 403-413 (1999-12-10)
The antimutagenic effect of ethanolic extract of propolis (EEP) and honeybee (Apis mellifera) venom, both collected in the State of São Paulo, Brazil, was assessed by the Salmonella/microsome assay upon direct- and indirect-acting mutagens. EEP had inhibitory effect (in an
J M Gentile et al.
Environmental mutagenesis, 7(1), 73-85 (1985-01-01)
The direct-acting mutagen 4-nitro-o-phenylenediamine (NOP) was activated in vitro by pea or tobacco S-9 into a more potent mutagen in Salmonella typhimurium strain TA98. NOP mutagenicity was not altered by Aroclor 1254-induced rat liver S-9. The plant S-9 activation of
Nahid Mashkouri Najafi et al.
Analytica chimica acta, 714, 82-88 (2012-01-17)
Herein, ultrasound-assisted emulsification microextraction (USAEME) and dispersive liquid-liquid microextraction (DLLME) methods based on applying low-density organic solvents have been critically compared for the speciation of inorganic selenium, Se(IV) (selenite) and Se(VI) (selenate) in environmental water samples by gas chromatography-flame ionization
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