2-Methoxy-4-nitroaniline

Synonym(s):4-Nitro-o-anisidine

CAS NO.：97-52-9
Empirical Formula: C7H8N2O3
Molecular Weight: 168.15
MDL number: MFCD00007363
EINECS: 202-588-6
SAFETY DATA SHEET (SDS)
Update Date: 2025-01-27 09:38:02

What is 2-Methoxy-4-nitroaniline?

Chemical properties

2-Methoxy-4-nitroaniline is a yellow to orange crystalline powder. 2-Methoxy-4-nitroaniline (MONA) is a potential nonlinear optical (NLO) material, the N12–O19 bond length of MONA molecule is essentially controlled by the p-character of these hybrid orbitals and also by the nature of the N12–O19 bond. The molecular geometry of the compound is almost planar with the substituents[1].

The Uses of 2-Methoxy-4-nitroaniline

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.

The Uses of 2-Methoxy-4-nitroaniline

2-Methoxy-4-nitroaniline is an important intermediate for preparing organic pigments and color bases of ice dyeing dyestuff. As a benzene dye intermediate, It is generally employed to prepare not only fast pigments but also as a printing and dyeing developer for cotton fabrics. In particular, 2-methoxy-4-nitroaniline is also important in production of some antineoplastic drugs[2-3].

General Description

2-Methoxy-4-nitroaniline is an important inducer of CYP1A2 owing to its small molecular size.

Flammability and Explosibility

Non flammable

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.

Solubility in organics

The change trend of the solubility magnitude in different monosolvents from high to low was as follows: N-methylpyrrolidone (NMP) > dimethyl sulfoxide (DMSO) > 1,4-dioxane > ethyl acetate > acetonitrile > ethanol > methanol > n-propanol > isopropanol > ethylene glycol (EG) > n-butanol > water[2].

References

[1] Bao Y, et al. 2-Methoxy-4-nitroaniline Solubility in Several Monosolvents: Measurement, Correlation, and Solvent Effect Analysis. Journal of Chemical & Engineering Data, 2020; 65: 757–765.
[2] Degawa M, et al.2-Methoxy-4-nitroaniline is a selective inducer of cytochrome P450IA2 (CYP1A2) in rat liver. Cancer Letters, 1995; 96: 95-98.
[3] Ravikumar C, et al. Electronic absorption and vibrational spectra and nonlinear optical properties of 4-methoxy-2-nitroaniline. Physical Chemistry Chemical Physics, 2010; 12: 9452-9460.

Properties of 2-Methoxy-4-nitroaniline

Melting point:	140-142 °C(lit.)
Boiling point:	337.07°C (rough estimate)
Density	1,211 g/cm³
refractive index	1.6010 (estimate)
storage temp.	Store below +30°C.
solubility	0.2g/l
pka	1.02±0.10(Predicted)
form	Crystalline Powder
color	Yellow to orange
PH	6.2 (0.2g/l, H2O, 20℃)
Water Solubility	slightly soluble
BRN	879619
CAS DataBase Reference	97-52-9(CAS DataBase Reference)
NIST Chemistry Reference	Benzenamine, 2-methoxy-4-nitro-(97-52-9)
EPA Substance Registry System	2-Methoxy-4-nitroaniline (97-52-9)

Safety information for 2-Methoxy-4-nitroaniline

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Health Hazard GHS08 Environment GHS09
GHS Hazard Statements	H302:Acute toxicity,oral H351:Carcinogenicity H411:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P202:Do not handle until all safety precautions have been read and understood. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P308+P313:IF exposed or concerned: Get medical advice/attention.