5-FLUOROINDOLE-3-CARBOXALDEHYDE Chemical Properties

Melting point:

164°C

Boiling point:

342.4±22.0 °C(Predicted)

Density 

1.385±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

crystalline

pka

14.66±0.30(Predicted)

color 

yellow to green

Sensitive 

Air Sensitive

BRN 

1449216

CAS DataBase Reference

2338-71-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-FLUOROINDOLE-3-CARBOXALDEHYDE Usage And Synthesis

Uses

5-Fluoroindole-3-carboxaldehyde is used as a reagent in the synthetic preparation of compounds requiring an indole group or more specifically a fluoroindole group.

Synthesis

GENERAL METHOD: Phosphoryl chloride (0.42 g, 2.74 mmol) was slowly added dropwise to a solution of N,N-dimethylformamide (0.84 g, 11.4 mmol) of 5-fluoroindole (0.30 g, 2.29 mmol) at 0 °C, the dropwise process lasted for 30 min. Subsequently, the reaction mixture was warmed up to 40 °C and kept for 1 hour. Upon completion of the reaction, ice was added to the reaction vessel followed by 2 M sodium hydroxide solution. The mixture was refluxed for 40 minutes. After the reaction solution was cooled to room temperature, it was extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of petroleum ether-ethyl acetate to give the target compound 5-fluoroindole-3-carboxaldehyde [19].

References

[1] Archiv der Pharmazie, 2017, vol. 350, # 1,
[2] Journal of the American Chemical Society, 2009, vol. 131, # 31, p. 10796 - 10797
[3] Marine Drugs, 2014, vol. 12, # 4, p. 1757 - 1772
[4] Patent: WO2015/90233, 2015, A1. Location in patent: Paragraph 00263
[5] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 344 - 367

5-FLUOROINDOLE-3-CARBOXALDEHYDE(2338-71-8)Related Product Information

• 5-FLUOROINDOLE-3-CARBOXYLIC ACID
• 5-Fluoroindole-2-carboxylic acid
• 5-FLUOROINDOLE-3-ACETIC ACID
• 4,5-DIFLUORO-2-METHYLINDOLE-3-CARBOXYLIC ACID ETHYL ESTER
• 7-FLUOROINDOLE-3-CARBOXALDEHYDE
• 5-FLUOROINDOLE-3-CARBOXALDEHYDE
• 6-FLUOROINDOLE-3-CARBOXALDEHYDE,6-FLUOROINDOLE-3-CARBOXALDEHYDE 98% (HPLC),1H-6-FLUOROINDOLE-3-CARBOXALDEHYDE
• Indole-3-carboxaldehyde
• 5-Fluoroindole
• 2-CHLORO-1-(5-FLUORO-2-METHYL-1H-INDOL-3-YL)-ETHANONE
• 4,5,6,7-TETRAFLUOROINDOLE-3-CARBOXALDEHYDE
• 5-FLUORO-3-FORMYL-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• 5-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE
• 4-FLUOROINDOLE-3-CARBOXALDEHYDE
• 7-Fluoroindole-3-carboxaldehyde
• 5-FLUORO-2-METHOXY-[1-[2-[(METHYLSULFONYL)AMINO]ETHYL]-4-PIPERIDINYL]-1H-INDOLE-3-METHYLCARBOXYLATE SULFAMATE
• 5-FLUORO-2-METHYLINDOLE-3-CARBOXYLIC ACID ETHYL ESTER
• 6-Fluoroindole-3-carboxaldehyde