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2-Methoxy-4-nitroaniline

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2-Methoxy-4-nitroaniline Basic information

Product Name:
2-Methoxy-4-nitroaniline
Synonyms:
  • redbasecibav
  • redbaseirgav
  • METHOXY-4-NITROANILINE
  • Brilliant Red Developing Base 4B
  • 4-NITRO-ORTHO-ANISIDINE
  • -Amino-5-nitrophenyl methyl ether
  • RED B ASE
  • RED B BASE
CAS:
97-52-9
MF:
C7H8N2O3
MW:
168.15
EINECS:
202-588-6
Product Categories:
  • Intermediates of Dyes and Pigments
  • Dyes and Pigments
  • Anilines, Amides & Amines
  • Anisoles, Alkyloxy Compounds & Phenylacetates
  • Nitro Compounds
Mol File:
97-52-9.mol
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2-Methoxy-4-nitroaniline Chemical Properties

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)
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Safety Information

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

MSDS

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2-Methoxy-4-nitroaniline Usage And Synthesis

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.

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