2034-22-2

BEIGE-YELLOW POWDER

2,4,5-Tribromoimidazole(2,4,5-TBI) on condensation with sugar precursors yields 2,4,5-TBI nucleosides.

2,4,5-Tribromoimidazole induces poisoning typical of uncouplers of oxidative phosphorylation in rats.

The general procedure for the synthesis of 2,4,5-tribromoimidazole from imidazole was as follows: to a three-necked flask equipped with a thermostatic separatory funnel was added imidazole (29.24 g, 0.43 mol), sodium acetate (317.34 g, 3.87 mol) and acetic acid (150 mL). The mixture was dissolved in additional acetic acid (100 mL). Bromine (65 mL, 1.28 mol) was added slowly dropwise through a thermostatic separatory funnel at room temperature, controlling the reaction temperature to not exceed 40°C. After the dropwise addition was completed, the reaction mixture continued to be stirred for 3 hours at room temperature. Upon completion of the reaction, the reaction solution was poured into 1.5 L of water to induce precipitation of the solid product. The solid product was collected by filtration and washed several times with water to remove impurities. Finally, the solid product was dried to afford the target compound 2,4,5-tribromoimidazole (120 g, 92% yield).

[1] Patent: CN106256830, 2016, A. Location in patent: Paragraph 0044; 0049; 0050; 0051
[2] Tetrahedron Letters, 2015, vol. 56, # 41, p. 5646 - 5650
[3] Tetrahedron Letters, 1998, vol. 39, # 44, p. 8163 - 8166
[4] Tetrahedron, 1999, vol. 55, # 4, p. 935 - 942
[5] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2740 - 2741