1-Methyl-1H-indole-6-carbaldehyde

1-Methyl-1H-indole-6-carbaldehyde Property

Melting point:

81 °C

Boiling point:

318.7±15.0 °C(Predicted)

Density 

1.10±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

2-8°C

form 

solid

Appearance

Light yellow to brown Solid

Safety

Hazard Codes 

Xi

Risk Statements 

41-52-36

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Methyl-1H-indole-6-carbaldehyde Chemical Properties,Usage,Production

Uses

1-methyl-1H-indole-6-carbaldehyde is used as a component of organic synthesis or pharmaceutical intermediates.

Synthesis

GENERAL METHOD: Indole-6-carboxaldehyde (435 mg, 3 mmol) was dissolved in acetonitrile (30 mL), cesium carbonate (829 mg, 6 mmol) was added, and the reaction mixture was heated and refluxed for 2 hours. Subsequently, iodomethane (3.3 mmol) was added to the reaction system and heating and refluxing was continued for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the residue and extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Finally, the resulting residue was purified by fast column chromatography to give the target product 1-methylindole-6-carbaldehyde.

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2060 - 2079
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5888 - 5891
[3] Patent: WO2004/52890, 2004, A1. Location in patent: Page 46-47