5-METHYLINDOLE-3-CARBOXALDEHYDE Chemical Properties

Melting point:

148-151 °C(lit.)

Boiling point:

348.2±22.0 °C(Predicted)

Density 

1.226±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

15.68±0.30(Predicted)

Appearance

Off-white to pink Solid

CAS DataBase Reference

52562-50-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

5-METHYLINDOLE-3-CARBOXALDEHYDE Usage And Synthesis

Uses

5-Methyl-1H-indole-3-carbaldehyde (cas# 52562-50-2) is a useful reagent for regio- and enantioselective preparation of N-alkylated indole- and pyrrole-3-carbaldehydes.

Uses

5-Methylindole-3-carboxaldehyde was used in the synthesis of novel flexible tripodal ligand derived from 3-methylindole and its mononuclear Zn(II),Cu(II), Ni(II), Hg(II) and Pd(II) complexes.

Synthesis

GENERAL STEPS: Oxalyl chloride (0.3 mL) was slowly added dropwise to cooled (ice bath) N,N-dimethylformamide (DMF, 3 mL) under stirring conditions. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, a solution of 5-methylindole (4 mmol) dissolved in DMF (1.5 mL) was added slowly dropwise to the above reaction mixture. The resulting mixture was stirred and reacted at room temperature for 5 hours. Upon completion of the reaction, 2N sodium hydroxide solution (2 mL) was added and the mixture was heated to 100 °C and maintained for 10 min. 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 finally obtain the purified 5-methyl-1H-indole-3-carbaldehyde.

References

[1] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[2] Patent: EP1932833, 2008, A1. Location in patent: Page/Page column 11; 12
[3] Chemistry - A European Journal, 2016, vol. 22, # 2, p. 716 - 723
[4] Marine Drugs, 2014, vol. 12, # 4, p. 1757 - 1772
[5] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 70 - 81

5-METHYLINDOLE-3-CARBOXALDEHYDE(52562-50-2)Related Product Information

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• 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER
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• 5-METHYLINDOLE-3-CARBOXALDEHYDE
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• 7-METHYLINDOLE-3-CARBOXALDEHYDE,7-Methylindole-3-carboxaldehyde 98%,7-METHYLINDOLE-3-CARBOXALDEHYDE 98% (HPLC)
• 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE
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• 2,5-DI-TERT-BUTYL-1H-INDOLE-3-CARBALDEHYDE
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• 1-METHYLINDOLE-2-CARBOXALDEHYDE 97
• 5-FLUORO-1-METHYLINDOLE-3-CARBOXALDEHYDE
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