2-Methoxy-4-nitroaniline Property

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

form 

Crystalline Powder

pka

1.02±0.10(Predicted)

color 

Yellow to orange

PH

6.2 (0.2g/l, H2O, 20℃)

Water Solubility 

slightly soluble

BRN 

879619

InChIKey

GVBHRNIWBGTNQA-UHFFFAOYSA-N

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

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-37/39-36/37

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

2

RTECS 

BZ7170000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29222900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H351Suspected of causing cancer

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

2-Methoxy-4-nitroaniline Chemical Properties,Usage,Production

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].

Uses

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].

Uses

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.

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.