4,7-DIBROMO-1H-INDOLE Chemical Properties

Melting point:

54-56°

storage temp. 

Sealed in dry,Room Temperature

Appearance

Off-white to brown Solid

Safety Information

HazardClass 

IRRITANT

4,7-DIBROMO-1H-INDOLE Usage And Synthesis

Uses

4,?7-?Dibromo-?1H-?indole is a reagent used in the synthesis of carbazole carboxamide based inhibitors used in the treatment of lymphomatic leukemia.

Synthesis

General procedure for the synthesis of 4,7-dibromo-1H-indoles from 2,5-dibromonitrobenzene and vinylmagnesium bromide: 1. To a solution of 1,4-dibromo-2-nitrobenzene (18 g, 64.1 mmol) in tetrahydrofuran (THF, 200 mL) was slowly added vinylmagnesium bromide (1.0 M solution in THF, 199 mL, 199 mmol) at -40 °C (dry ice-acetonitrile bath). 2. The reaction mixture was stirred continuously at -40 °C for 1.5 hours. 3. the reaction was quenched with saturated aqueous ammonium chloride (NH4Cl) solution (500 mL) followed by stirring for 1 hour at room temperature. 4. pH was adjusted to 7 by adding 1 M hydrochloric acid (HCl). 5. Ethyl acetate (EtOAc) was added for extraction, the organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. 6. The crude product was purified by silica gel column chromatography (330 g silica gel) using ethyl acetate-hexane (5:95) as eluent. 7. The target fraction was collected and concentrated under reduced pressure to give a light yellow oil, which solidified to a solid on standing. 8. 4,7-dibromo-1H-indole (8.35 g, 47% yield) was finally obtained, LCMS analysis showed the main peak, no ionization was observed.

References

[1] Synlett, 1999, # 10, p. 1594 - 1596
[2] Organic Letters, 2010, vol. 12, # 9, p. 2162 - 2165
[3] Patent: WO2011/159857, 2011, A1. Location in patent: Page/Page column 200
[4] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
[5] Patent: WO2010/145203, 2010, A1. Location in patent: Page/Page column 17

4,7-DIBROMO-1H-INDOLE(126811-31-2)Related Product Information

• 4,7-DIBROMO-2-METHYL-1H-INDOLE
• 4,7-DIBROMO-1H-INDOLE
• 2-(4,7-DIBROMO-2-METHYL-1H-INDOL-3-YL)ETHANAMINE HYDROCHLORIDE