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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:
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

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

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

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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