Methyl-4-amino-3-fluorobenzoate Chemical Properties

Melting point:

109-110°C

Boiling point:

296℃

Density 

1.264

Flash point:

133℃

storage temp. 

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

form 

powder

pka

1.07±0.10(Predicted)

color 

White to off-white

Safety Information

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37/39-45

HazardClass 

IRRITANT

HS Code 

2922500090

Methyl-4-amino-3-fluorobenzoate Usage And Synthesis

Uses

4-Amino-3-fluorophenylcarboxylic acid methyl ester is a carboxylic acid ester derivative that can be used as a pharmaceutical intermediate.

Chemical Properties

Brown solid

Synthesis

General procedure for the synthesis of methyl 4-amino-3-fluorobenzoate from methyl 3-fluoro-4-nitrobenzoate: Methyl 3-fluoro-4-nitrobenzoate (2.50 g, 12.5 mmol) and Pd/C catalyst (300 mg, 10 wt%) were placed in a 1:1 EtOAc/EtOH solvent mixture (40 mL). The reaction mixture was stirred at room temperature and 1 atm hydrogen atmosphere for 16 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to afford methyl 4-amino-3-fluorobenzoate (2.1 g, 99% yield) as a beige solid. Mass spectrometry analysis (ES+): the theoretical molecular weight of C8H8FNO2 was 169 and the measured value was 170 [M + H]+.

References

[1] Patent: WO2018/81276, 2018, A1. Location in patent: Page/Page column 154
[2] Patent: EP3401315, 2018, A1. Location in patent: Paragraph 0096; 0097
[3] Patent: WO2007/16392, 2007, A2. Location in patent: Page/Page column 48
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[5] Patent: US2003/232889, 2003, A1. Location in patent: Page/Page column 15

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