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ChemicalBook CAS DataBase List 3,6-dibroMo-1,2-BenzenediaMine
69272-50-0

3,6-dibroMo-1,2-BenzenediaMine synthesis

8synthesis methods
-

Yield:30757-50-7 98%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 0 - 20; for 20 h;

Steps:

Preparation of compound 1.

Sodium borohydride (4.2 g, 110 mmol) was added portion wise into a solution of 4,7-Dibromo-2,1,3-Benzothiadiazole (3.3 g, 11.2 mmol) in ethanol (100 mL) at 0 °C. The resulting mixture was stirred at room temperature for 20 h. The reaction mixture was quenched by adding 50 mL of water, and extracted with CH2Cl2 (40 mL 2). The combined organic layers were washed with water and brine successively, dried over anhydrous sodium sulfate. Removing the solvent under rotary evaporator, the crude product was purified by column chromatography using hexane/ethyl acetate (5/1, v/v) as an eluent to afford compound 1 as an white solid (2.9 g, yield: 98%), mp: 128.2-131.3 °C. 1H NMR (600 MHz, CDCl3) δ: 6.84 (s, 2H), 3.89 (s, 4H). 13C NMR (150 MHz, CDCl3) δ: 133.7, 123.3, 109.7. Anal. calcd for C6H6Br2N2: C, 27.10; H, 2.27; N, 10.53; found: C, 27.04; H, 2.28; N, 10.49.

References:

Chen, Hongjin;Han, Yiying;Liu, Jian;Wang, Wenyuan;Zhu, Jianjun [Polymer,2022,vol. 240,art. no. 124485]