2-Methoxy-4-nitroaniline CAS 97-52-9

Introduction：Basic information about 2-Methoxy-4-nitroaniline CAS 97-52-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

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

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
• 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
• InChI: 1S/C7H8N2O3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,8H2,1H3
• InChIKey: GVBHRNIWBGTNQA-UHFFFAOYSA-N
• SMILES: COc1cc(ccc1N)[N+]([O-])=O
• 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

• 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: TSCA listed
• HS Code: 29222900
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral Aquatic Chronic 2 Carc. 2

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 used as a photometric reagent for the determination of ethinylestradiol (ETE), a semi-synthetic estrogen that is widely used in oral contraceptives.

Uses

2-Methoxy-4-nitroaniline is an important intermediate for preparingorganic pigments and color bases of ice dyeing dyestuff. As a benzene dye intermediate, It isgenerally employed to prepare not only fast pigments but alsoas 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.

2-Methoxy-4-nitroaniline Preparation Products And Raw materials

• Raw materials: Acetic acid-->Nitric acid-->Tosyl chloride-->o-Anisidine-->PARA TOLUENE-->N-(2-Methoxyphenyl)acetamide
• Preparation Products: 4-Fluoro-3-methoxyaniline-->8-METHOXYQUINOLIN-6-AMINE-->5-CHLORO-2-NITROANISOLE-->C.I.Pigment Yellow 98-->2-Chloro-5-aminophenol-->Pigment Yellow 74-->2-METHOXY-4-NITROBENZALDEHYDE-->2,5-DIBROMOANISOLE-->Benzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul-->sodium 4-hydroxy-5-[(2-methoxy-4-nitrophenyl)azo]-6-(phenylamino)naphthalene-2-sulphonate-->2,2'-[[4-[(4-Amino-2-methoxyphenyl)azo]-3-methylphenyl]imino]bisethanol-->Solvent Red 13-->Copper, diazotized 2-methoxy-4-nitrobenzenamine-4-[(8-hydroxy-6-sulfo-2-naphthalenyl)amino]benzoic acid coupling products complexes-->4-[(2-methoxy-4-nitrophenyl)azo]-N,N-dimethyl-Benzenamine