5-CHLORO-2-METHYLINDOLE Chemical Properties

Melting point:

112-118 °C

Boiling point:

140 °C / 0.1mmHg

Density 

1.1705 (rough estimate)

refractive index 

1.5390 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

16.66±0.30(Predicted)

color 

White to Gray to Brown

InChIKey

WUVWAXJXPRYUME-UHFFFAOYSA-N

CAS DataBase Reference

1075-35-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-CHLORO-2-METHYLINDOLE Usage And Synthesis

Chemical Properties

light pink to beige-pale brown crystalline powder

Uses

2-Methyl-5-chloroindole has been shown to depress brainstem and telencephalon serotonin for 3 days after 24 hours of being administered intraventricularly.Dyes and metabolites.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 5495, 1974 DOI: 10.1021/ja00824a028

Synthesis

In a 100 mL stainless steel autoclave, 1.09 g (5.1 mmol) of 5-chloro-2-nitrophenylacetone and 72 mg (4 mol%) of cyclopentadienyl ferric dicarbonyl (dimer) were added as a catalyst and 40 g of toluene as a solvent, and the system was protected by nitrogen. After displacing the atmosphere in the reactor three times (10 kgf/cm2 nitrogen each time), carbon monoxide gas was injected to a pressure of 30 kgf/cm2. The reaction mixture was stirred at 120 °C for 5 h. The reaction was completed by cooling to room temperature. Upon completion of the reaction, it was cooled to room temperature and the complete conversion of 5-chloro-2-nitrophenylacetone was confirmed by liquid chromatography analysis. Subsequently, the reaction mixture was post-treated and purified by silica gel column chromatographic separation to afford 0.79 g (94.0% yield) of the target product 5-chloro-2-methylindole.

References

[1] Patent: US2007/83053, 2007, A1. Location in patent: Page/Page column 7

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