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5-Chloro-1H-indole-2-carbaldehyde

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5-Chloro-1H-indole-2-carbaldehyde Basic information
Product Name:5-Chloro-1H-indole-2-carbaldehyde
Synonyms:5-chloro-indole-2-carbaldehyde;1H-Indole-2-carboxaldehyde, 5-chloro-;5-Chloro-1H-indole-2-carbaldehyde ,97%;5-Chloroindole-2-carboxaldehyde;5-Chloro-1H-indole-2-carbaldehyde
CAS:53590-49-1
MF:C9H6ClNO
MW:179.6
EINECS:
Product Categories:
Mol File:53590-49-1.mol
5-Chloro-1H-indole-2-carbaldehyde Structure
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
pka14.14±0.30(Predicted)
AppearanceOff-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
MSDS Information
5-Chloro-1H-indole-2-carbaldehyde Usage And Synthesis
Chemical PropertiesLight yellow solid
Synthesis
(5-chloro-1H-indol-2-yl)methanol

53590-47-9

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

53590-49-1

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
5-Chloro-1H-indole-2-carbaldehyde Preparation Products And Raw materials
Raw materials(5-chloro-1H-indol-2-yl)methanol
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