4-BROMO-7-METHOXY-1H-INDOLE Chemical Properties

Boiling point:

356.5±22.0 °C(Predicted)

Density 

1.591±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

15.56±0.30(Predicted)

Appearance

Light yellow to brown Solid-Liquid Mixture

4-BROMO-7-METHOXY-1H-INDOLE Usage And Synthesis

Uses

4-BROMO-7-METHOXY-1H-INDOLE has garnered interest due to its potential biological activities and applications in the synthesis of pharmaceuticals and organic chemistry, serving as a valuable building block and chemical intermediate.

Synthesis

Example 13 Synthesis of 4-bromo-7-methoxyindole (LII): to a tetrahydrofuran (THF) solution (300 ml) of 4-bromo-2-nitroanisole (7.89 g, 33.3 mmol) was slowly added vinylmagnesium bromide (1 M in THF) at -60 °C. The reaction temperature was kept below -40 °C while the reaction mixture was stirred so that the temperature was gradually raised to -40 °C within 2 hours. After completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl) solution (100 ml, 0.1 mol). The aqueous phase was extracted with ether (Et2O, 200 ml), the organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. Finally, the target product 4-bromo-7-methoxyindole (LII, 594 mg, 8% yield) was purified by fast chromatography.

References

[1] Patent: WO2009/62285, 2009, A1. Location in patent: Page/Page column 111
[2] Patent: US2007/123527, 2007, A1. Location in patent: Page/Page column 67-68