5-CHLORO-1H-INDOLE-2-CARBALDEHYDE Chemical Properties

Melting point:

204-206 °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

14.14±0.30(Predicted)

Appearance

Off-white to brown Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-20/21/22

Safety Statements 

26-36/37

HazardClass 

IRRITANT

HS Code 

29339900

5-CHLORO-1H-INDOLE-2-CARBALDEHYDE Usage And Synthesis

Chemical Properties

Light yellow solid

Synthesis

General procedure for the synthesis of 5-chloro-1H-indole-2-carboxaldehyde from (5-chloro-1H-indol-2-yl)methanol: (5-chloro-1H-indol-2-yl)methanol (1 eq.) was dissolved in tetrahydrofuran (THF, 0.5 M), manganese dioxide (3 eq.) was added, the reaction was stirred for 1.5 hr. at room temperature, and the progress of the reaction was monitored by thin layer chromatography (TLC) until the complete conversion of the feedstock. After completion of the reaction, the mixture was filtered through a diatomaceous earth pad, the filtrate was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent to give the crude 5-chloro-1H-indole-2-carbaldehyde in 82% yield.

References

[1] Synlett, 2007, # 11, p. 1707 - 1710
[2] Chemical Communications, 2013, vol. 49, # 28, p. 2894 - 2896
[3] Patent: US2008/9485, 2008, A1. Location in patent: Page/Page column 41
[4] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 561 - 577
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 6, p. 1889 - 1900

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