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Sigma-Aldrich

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:
97-52-9
Molecular Weight:
168.15
Beilstein:
879619
EC Number:
202-588-6
MDL number:
MFCD00007363
UNSPSC Code:
12352100
PubChem Substance ID:
24847104
NACRES:
NA.22

Quality Level

100

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

H302,H351,H411

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

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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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)
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
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
Rachel P Frawley et al.
Toxicology, 441, 152474-152474 (2020-05-08)
2-Methoxy-4-nitroaniline (MNA), an intermediate in the synthesis of azo dyes used in textiles and paints, is structurally similar to carcinogenic anilines. Human exposure occurs primarily in the occupational setting through handling of dye dust, and through use and disposal of

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