5-Chloro-6-fluoro-1H-indole Chemical Properties

Melting point:

83 °C

Boiling point:

299.8±20.0 °C(Predicted)

Density 

1.436±0.06 g/cm3(Predicted)

storage temp. 

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

pka

15.49±0.30(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933998090

5-Chloro-6-fluoro-1H-indole Usage And Synthesis

Application

5-Chloro-6-fluoroindole can be used as a pharmaceutical synthesis intermediate.

Synthesis

General procedure for the synthesis of 5-chloro-6-fluoroindole from methyl (4-chloro-5-fluoro-2-((trimethylsilyl)ethynyl)phenyl)carbamate: dissolve the crude (4-chloro-5-fluoro-2-trimethylsilylethynylphenyl)carbamate methyl ester (ca. 21 mmol) in tetrahydrofuran (200 mL) and add tetrabutylammonium fluoride (43.3 mL, 1 M in tetrahydrofuran, 43.3 mmol). The reaction was carried out at room temperature. After stirring for 5 minutes, the reaction mixture was refluxed for 1 hour under argon protection. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting oil was treated with water (55 mL), stirred for 10 minutes and subsequently extracted twice with ethyl acetate (100 mL). The combined organic phases were washed sequentially with 1 M aqueous hydrochloric acid (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated aqueous sodium chloride (50 mL), and finally dried with magnesium sulfate. The dried organic phase was filtered and concentrated under reduced pressure. The residue was stirred with hexane (200 mL) under reflux, cooled to 5 °C and filtered to afford 5-chloro-6-fluoro-1H-indole (3.15 g, 85% yield) as a light brown solid. Mass spectrometry (EI) showed a molecular ion peak m/z 169.1 (M+).

References

[1] Patent: US2007/185182, 2007, A1. Location in patent: Page/Page column 12
[2] Patent: US2006/30613, 2006, A1. Location in patent: Page/Page column 30

5-Chloro-6-fluoro-1H-indole(169674-57-1)Related Product Information

• 5-FLUOROINDOLE-3-CARBOXYLIC ACID
• 6-BROMO-4-INDOLE CARBOXYLIC ACID
• 6-Methylindole
• 6-BROMO-4-METHOXYINDOLE
• 6-BROMO-5-METHYLINDOLE
• 6-Chloro-4-methoxyindole
• 6-CHLOROINDOLE-3-CARBOXYLIC ACID
• 5-CHLORO-1H-INDOL-3-METHYLAMINE
• 5-METHYLINDOLE-2-CARBOXYLIC ACID
• 6-BROMO-4-INDOLECARBOXYLIC ACID METHYL ESTER
• Ethyl 5-cyanoindole-2-carboxylate
• 5-CHLORO-4-FLUOROINDOLE
• 4-Chloro-5-fluoroindole
• 6-CHLORO-5-FLUOROINDOLE
• 6-Fluoroindole
• 5-CHLORO-6-FLUOROINDOLE
• 7-CHLORO-4-FLUOROINDOLE
• 4-CHLORO-7-FLUOROINDOLE