4-Fluoroindole-2-carboxylic acid

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4-Fluoroindole-2-carboxylic acid Basic information
Product Name:4-Fluoroindole-2-carboxylic acid
Synonyms:INDOLE-2-CARBOXYLIC ACID, 4-FLUORO-;4-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID;4-FLUOROINDOLE-2-CARBOXYLIC ACID;1H-Indole-2-carboxylic acid, 4-fluoro-;4-Fluoro-1H-indol-2-carboxylic acid
CAS:399-68-8
MF:C9H6FNO2
MW:179.15
EINECS:
Product Categories:pharmacetical;Indole
Mol File:399-68-8.mol
4-Fluoroindole-2-carboxylic acid Structure
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
pka4.32±0.30(Predicted)
color Pale yellow
CAS DataBase Reference399-68-8(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
HS Code 2933998090
MSDS Information
4-Fluoroindole-2-carboxylic acid Usage And Synthesis
Synthesis
Benzenepropanoic acid, 4-fluoro-2-nitro-α-oxo-

7593-91-1

4-Fluoroindole-2-carboxylic acid

399-68-8

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
4-Fluoroindole-2-carboxylic acid Preparation Products And Raw materials
Raw materialsBenzenepropanoic acid, 4-fluoro-2-nitro-α-oxo--->iron dihydroxide-->Ammonium hydroxide
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