4-Fluoroindole-2-carboxylic acid Chemical Properties

Melting point:

219-220 °C (decomp)

Boiling point:

422.2±25.0 °C(Predicted)

Density 

1.510±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder

pka

4.32±0.30(Predicted)

color 

Pale yellow

CAS DataBase Reference

399-68-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933998090

4-Fluoroindole-2-carboxylic acid Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-fluoroindole-2-carboxylic acid from the compound (CAS: 7593-91-1): 4.8 g (31 mmol) of compound 32 was dissolved in 60 mL of 4% NH4OH solution, which was subsequently added to a solution prepared from 52.45 g (188.7 mmol) of ferrous sulfate heptahydrate and 23 mL of concentrated NH4OH in 200 mL of water in a suspension of ferrous hydroxide. The reaction mixture was kept at boiling point for 5 minutes. Upon completion of the reaction, the resulting iron hydroxide precipitate was separated by filtration and washed repeatedly with dilute NH4OH and water. The filtrate was acidified with dilute HCl to a suitable pH and the precipitated solid was subsequently collected by filtration to afford 1.2 g (22% yield) of 4-fluoro-1H-indole-2-carboxylic acid (34) as a white solid. The resulting product could be used directly in the next step of the reaction without further purification.

References

[1] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 944 - 948
[2] Patent: US2014/66453, 2014, A1. Location in patent: Paragraph 0184-0185

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