4-Bromo-3-methyl-indole Chemical Properties

Melting point:

ca. 25-30℃

Boiling point:

325.1±22.0 °C(Predicted)

Density 

1.563±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder

pka

16.37±0.30(Predicted)

color 

White

Sensitive 

Light Sensitive

Safety Information

HS Code 

2933998090

4-Bromo-3-methyl-indole Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-bromo-3-methyl-1H-indole from 4-bromoindole-3-carboxaldehyde: Lithium aluminum hydride (LAH, 1.0 M tetrahydrofuran (THF) solution, 5.75 mL, 5.75 mmol) was added slowly and dropwise to refluxed 4-bromo-1H-indole-3-carboxaldehyde (644 mg, 2.87 mmol) in anhydrous THF (20 mL); Intermediate 27) solution. The reaction mixture was refluxed for 1 h and cooled to room temperature. The reaction was quenched sequentially by the addition of water (220 μL), 15% aqueous sodium hydroxide solution (220 μL) and water (650 μL). The resulting precipitate was collected by filtration, the filtrate was concentrated, and the residue was extracted with aqueous sodium hydroxide (10 mL) and dichloromethane (2 x 10 mL). The organic layer was combined with a previous batch (from 4-bromo-1H-indole-3-carboxaldehyde, 100 mg, 0.45 mmol; starting with Intermediate 27) of this intermediate, dried and concentrated to give the title compound (556 mg, 80% yield) as a light brown oil. Mass spectrometry (ESI+) analysis showed the molecular ion peak m/z 210 (M+H)+ for C9H8BrN.

References

[1] Patent: WO2008/3703, 2008, A1. Location in patent: Page/Page column 85-86
[2] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 160
[3] Patent: WO2013/16197, 2013, A1. Location in patent: Page/Page column 80-81
[4] Patent: WO2015/66344, 2015, A1. Location in patent: Page/Page column 223
[5] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107

4-Bromo-3-methyl-indole(475039-81-7)Related Product Information

• 5-CHLORO-3-METHYLINDOLE
• 5-Bromoindole-3-carboxaldehyde
• 1H-Indole, 7-broMo-3-Methyl-
• 7-BROMO-1H-INDOLE-3-CARBALDEHYDE
• 6-broMo-3-Methyl-1H-indole
• 3-Acetylindole
• 6-Bromoindole-3-carboxaldehyde