4-Chloroindole-3-carbaldehyde Chemical Properties

Melting point:

164 °C

Boiling point:

373.4±22.0 °C(Predicted)

Density 

1.431±0.06 g/cm3(Predicted)

storage temp. 

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

pka

14.60±0.30(Predicted)

Appearance

Light brown to brown Solid

CAS DataBase Reference

876-72-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

Hazard Note 

Irritant

HS Code 

2933998090

4-Chloroindole-3-carbaldehyde Usage And Synthesis

Synthesis

Trichlorophosphorus (3.55 mL) was added slowly and dropwise to N,N-dimethylformamide (10.63 mL) in stirring at 10-20 °C. Subsequently, a solution of 4-chloroindole (2 g, 13.19 mmol) was added at 20-30 °C. The reaction mixture was stirred at 35-37 °C for 45 min, after which it was poured into a stirred mixture of ice (28 g) and water (21 mL). The pH of the reaction solution was adjusted to 8 by adding a solution of sodium hydroxide (6.86 g) in water (36 mL) at 20-30 °C. The mixture was boiled for 5 min, cooled to room temperature and then extracted with ethyl acetate and washed with brine. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with 60% petroleum ether/ethyl acetate as eluent to give 4-chloroindole-3-carboxaldehyde (1.037 g, 44% yield) as an off-white solid. m/z = 180 [M+H]+ by LC-MS.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9179 - 9195
[2] Organic Letters, 2013, vol. 15, # 17, p. 4330 - 4333
[3] Patent: WO2016/44777, 2016, A1. Location in patent: Page/Page column 72; 73
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1793 - 1798
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6647 - 6651

4-Chloroindole-3-carbaldehyde(876-72-2)Related Product Information

• Indole-3-acetic acid
• Indole-3-butyric acid
• 4-Chloroindole
• Indometacin
• 5-BROMO-1H-INDOLE-2-CARBALDEHYDE
• Formaldehyde
• 5-Chloroindole-3-carboxaldehyde
• 6-Chloroindole-3-carboxaldehyde
• Methyl4-chloro-1H-indole-3-carboxylate
• 2-TERT-BUTYL-4-CHLORO-7-METHYL-1H-INDOLE-3-CARBALDEHYDE
• ETHYL 4,6-DICHLORO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE
• 4-CHLOROINDOLE-3-CARBOXYLIC ACID
• 4-Chloroindole-3-carbaldehyde
• RARECHEM AL BI 1257
• 1H-Indole-3-carboxylic acid, 2-aminomethyl-1-ethyl-4,5,6,7-tetrachloro -, ethyl ester
• 4-CHLORO-1-(4-METHYLPYRIMIDIN-2-YL)-1H-INDOLE-3-CARBOXYLIC ACID
• RARECHEM AL BF 1257
• 4-CHLORO-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER