4-METHOXY-3-NITROANILINE Chemical Properties

Melting point:

46-47 °C

Boiling point:

356.9±22.0 °C(Predicted)

Density 

1.318±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Acetonitrile (Slightly), Chloroform (Slightly)

form 

Solid

pka

3.33±0.10(Predicted)

color 

Dark Red

InChI

InChI=1S/C7H8N2O3/c1-12-7-3-2-5(8)4-6(7)9(10)11/h2-4H,8H2,1H3

InChIKey

RUFOHZDEBFYQSV-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(OC)C([N+]([O-])=O)=C1

CAS DataBase Reference

577-72-0(CAS DataBase Reference)

NIST Chemistry Reference

P-anisidine, 3-nitro-,(577-72-0)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2922290090

4-METHOXY-3-NITROANILINE Usage And Synthesis

Chemical Properties

orange red solid

Uses

4-Methoxy-3-nitroaniline is a chemical compound that has been shown to have anti-tumor and anti-inflammatory effects. It belongs to the class of amines and can be synthesized by nitrating 4-methoxy aniline.

Synthesis

2-Nitro-4-aminophenol (10.0 g, 64.9 mmol) was used as starting material and mixed with cesium carbonate (21 g, 64 mmol) and iodomethane (9.22 g, 64.9 mmol) in acetonitrile (1500 mL). The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble solids. The filtrate was concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by fast column chromatography (eluent: chloroform) to give 5.03 g of 4-methoxy-3-nitroaniline in 46% yield as a red oil. The structure of the product was confirmed by 1H NMR (DMSO-d6) δ 7.09-7.03 (m, 2H), 6.87 (d, J=3Hz, 1H), 5.21 (bs, 2H), 3.77 (s, 3H) and HRMS (EI) m/z 168.0497 (M+1). Elemental analysis results (C7H8N2O3): calculated values C 50.00, H 4.80, N 16.66; measured values C 50.20, H 5.07, N 16.60.

References

[1] Patent: US2002/26052, 2002, A1

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