112631
2-Methoxy-4-nitroaniline
98%
Synonym(s):
4-Nitro-o-anisidine
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About This Item
Linear Formula:
CH3OC6H3(NO2)NH2
CAS Number:
Molecular Weight:
168.15
Beilstein:
879619
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
mp
140-142 °C (lit.)
SMILES string
COc1cc(ccc1N)[N+]([O-])=O
InChI
1S/C7H8N2O3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,8H2,1H3
InChI key
GVBHRNIWBGTNQA-UHFFFAOYSA-N
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General description
2-Methoxy-4-nitroaniline is an important inducer of CYP1A2 owing to its small molecular size.
Application
2-Methoxy-4-nitroaniline is used as a photometric reagent for the determination of ethinylestradiol (ETE), a semi-synthetic estrogen that is widely used in oral contraceptives.
Biochem/physiol Actions
The metabolism of 2-methoxy-4-nitroaniline (MNA) occurs via the hydroxylation of the phenyl ring to form 6-hydroxy MNA in Harlan Sprague Dawley rats and B6C3F(1)/N mice.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 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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Use of nitroanilines for spectrophotometric determination of ethinylestradiol in pharmaceutical formulations.
Leonardo SG, et al.
Analytical Methods : Advancing Methods and Applications, 3(5), 1198-1201 (2011)
M Degawa et al.
Cancer letters, 96(1), 95-98 (1995-09-04)
Male F344 rats were treated with a chemical (aniline, nitrobenzene, 2-methoxy-p-phenylenediamine, 2-methoxy-4-nitroaniline or 2-methoxy-4-nitroazobenzene) produced by the azo-reduction and/or N-oxidation of 2-methoxy-4-amino-azo-benzene, a selective inducer of cytochrome P450IA2 (CYP1A2), and their effects on the induction of CYP1A enzymes in the
James M Mathews et al.
Xenobiotica; the fate of foreign compounds in biological systems, 42(12), 1213-1224 (2012-06-26)
The disposition of 2-Methoxy-4-nitroaniline (MNA) was investigated in male and female Harlan Sprague Dawley rats and B6C3F(1)/N mice following oral, intravenous, and dermal exposure to [(14)C]MNA at 2, 15, or 150 mg/kg. Clearance of MNA was investigated in male and
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