4-Amino-2-methoxy-phenol Chemical Properties

Melting point:

178.0 to 182.0 °C

Boiling point:

308.1±27.0 °C(Predicted)

Density 

1.219±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

10.23±0.18(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C7H9NO2/c1-10-7-4-5(8)2-3-6(7)9/h2-4,9H,8H2,1H3

InChIKey

MCNBYOWWTITHIG-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(N)C=C1OC

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RTECS 

SJ6072000

HS Code 

2922.50.5000

HazardClass 

IRRITANT

4-Amino-2-methoxy-phenol Usage And Synthesis

Chemical Properties

Dark-Brown Crystalline Solid

Synthesis

General procedure for the synthesis of 4-amino-2-methoxyphenol from 2-methoxy-4-nitrophenol: A mixed solution of 2-methoxy-4-nitrophenol (3.00 g, 17.7 mmol), 10% palladium-carbon catalyst (300 mg), tetrahydrofuran (100 mL), and methanol (100 mL) was subjected to a hydrogen atmosphere with stirring for 4 h at room temperature. Upon completion of the reaction, insoluble impurities were removed by filtration, followed by distillation under reduced pressure to remove the solvent, to afford 4-amino-2-methoxyphenol as a solid product in a yield of 2.32 g (94.3% yield). The product was characterized by 1H-NMR (CDCl3) with chemical shifts δ of 3.40 (2H, broad peak), 5.50 (1H, broad peak), 6.21 (1H, double peak, J = 8.2, 2.6 Hz), 6.30 (1H, double peak, J = 2.6 Hz), and 8.72 (1H, double peak, J = 8.2 Hz).

References

[1] Green Chemistry, 2015, vol. 17, # 2, p. 785 - 790
[2] Patent: EP1437344, 2004, A1. Location in patent: Page 49
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 13, p. 3881 - 3891
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 71 - 90
[5] Journal of Chemical Research, Miniprint, 1988, # 9, p. 2236 - 2261

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