6-FLUOROINDOLE-3-CARBOXALDEHYDE Chemical Properties

Melting point:

174-178°C

Boiling point:

342.4±22.0 °C(Predicted)

Density 

1.385±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in methanol.

form 

crystalline

pka

14.90±0.30(Predicted)

color 

yellow

CAS DataBase Reference

2795-41-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

6-FLUOROINDOLE-3-CARBOXALDEHYDE Usage And Synthesis

Chemical Properties

Yellow crystal

Uses

6-Fluoroindole-3-carboxaldehyde is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Synthesis

GENERAL STEPS: Oxalyl chloride (0.3 mL) was slowly added dropwise to cooled (ice bath) N,N-dimethylformamide (3 mL) under stirring conditions. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, 6-fluoroindole (4 mmol) was dissolved in N,N-dimethylformamide (1.5 mL) and the resulting solution was added slowly dropwise to the above reaction mixture. The reaction system was stirred at room temperature for 5 hours. Upon completion of the reaction, 2 N sodium hydroxide solution (2 mL) was added and the mixture was heated to 100 °C and held for 10 minutes. The reaction solution was cooled and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography with the eluent of ethyl acetate/petroleum ether (3:1, v/v) to obtain pure 6-fluoroindole-3-carbaldehyde.

References

[1] Journal of the American Chemical Society, 2009, vol. 131, # 31, p. 10796 - 10797
[2] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 10, p. 3307 - 3312
[4] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 2, p. 261 - 269
[5] Patent: CN103664895, 2018, B. Location in patent: Paragraph 0124-0126

6-FLUOROINDOLE-3-CARBOXALDEHYDE(2795-41-7)Related Product Information

• 6-fluoroindole-3-acetonitrile
• 6-Fluoroindoline
• 6-FLUOROINDOLE-3-ACETIC ACID
• Ethyl 6-fluoroindole-2-carboxylate
• 1H-Isoindol-1-one,6-fluoro-2,3-dihydro-(9CI)
• 6-Fluoroindole-2-carboxylic acid
• 6-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• 6-FLUORO-1H-INDOLE-3-CARBOXYLIC ACID
• 5-FLUOROINDOLE-3-CARBOXALDEHYDE
• 7-FLUOROINDOLE-3-CARBOXALDEHYDE
• 6-FLUORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• 6-FLUOROINDOLE-3-CARBOXALDEHYDE
• 6-Fluoroindole
• 4-FLUOROINDOLE-3-CARBOXALDEHYDE
• 6-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE
• 6-FLUORO-2-METHYLINDOLE-3-CARBOXYLIC ACID ETHYL ESTER
• 5,6-DIFLUORO-1H-INDOLE-3-CARBOXYLIC ACID
• 4,5,6,7-TETRAFLUOROINDOLE-3-CARBOXALDEHYDE