4-HYDROXY-5-METHOXY-2-NITRO-BENZOIC ACID METHYL ESTER Chemical Properties

Boiling point:

389.2±42.0 °C(Predicted)

Density 

1.405±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

6.63±0.24(Predicted)

Appearance

Brown to reddish brown Solid

InChI

InChI=1S/C9H9NO6/c1-15-8-3-5(9(12)16-2)6(10(13)14)4-7(8)11/h3-4,11H,1-2H3

InChIKey

SKKNLIAUOSEGNQ-UHFFFAOYSA-N

SMILES

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2916310090

4-HYDROXY-5-METHOXY-2-NITRO-BENZOIC ACID METHYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 4-hydroxy-5-methoxy-2-nitrobenzoate from methyl 4-benzyloxy-5-methoxy-2-nitrobenzoate: Methyl 2-nitro-4-benzyloxy-5-methoxybenzoate (4.1 mmol, 1.3 g) was dissolved in trifluoroacetic acid (8 mL), and the reaction was carried out at reflux for 1 hour. Upon completion of the reaction, trifluoroacetic acid was removed by decantation and the reaction mixture was extracted with water and ethyl acetate. The organic phases were combined, concentrated and purified by column chromatography to give 0.796 g methyl 2-nitro-4-hydroxy-5-methoxybenzoate in 86% yield.

References

[1] Patent: CN105884699, 2016, A. Location in patent: Paragraph 0064; 0065
[2] Patent: WO2016/148674, 2016, A1. Location in patent: Page/Page column 114
[3] Bioorganic and medicinal chemistry, 2004, vol. 12, # 16, p. 4337 - 4350
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 15, p. 6518 - 6545
[5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2989 - 2992