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ChemicalBook CAS DataBase List 5-BROMO-1H-BENZOTRIAZOLE
32046-62-1

5-BROMO-1H-BENZOTRIAZOLE synthesis

3synthesis methods
4-Bromo-1,2-benzenediamine

1575-37-7

5-BROMO-1H-BENZOTRIAZOLE

32046-62-1

The general procedure for the synthesis of 5-bromo-1H-benzotriazole from 4-bromo-o-phenylenediamine was as follows: 4-bromobenzene-1,2-diamine (10 g, 53.5 mmol) was dissolved in a mixture of acetic acid (20 ml, 349 mmol) and water (100 ml) in an ice-bath at 0-5 °C. A solution of sodium nitrite (4.06 g, 58.8 mmol) in water (10 ml) was added slowly and dropwise. The ice bath condition was maintained and the reaction mixture was stirred for 1 hour. Subsequently, additional acetic acid (20 ml, 349 mmol) was added and the reaction system was heated to 80-85°C and stirring was continued for 1 hour. Upon completion of the reaction, the hot solution was filtered to remove insoluble black impurities. The filtrate was cooled to 0-5 °C and left to age for 30 min. The precipitate precipitated was washed with water and dried under vacuum at 45 °C to afford the target product 5-bromo-1H-benzotriazole in a yield of 9.48 g (90% yield).

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: 97 percent / H2NNH2; FeCl3*6H2O / methanol
2: 75 percent / NaNO2; 5 percent AcOH

References:

Young, Jonathan R.;Huang, Song X.;Walsh, Thomas F.;Wyvratt Jr., Matthew J.;Yang, Yi Tien;Yudkovitz, Joel B.;Cui, Jisong;Mount, George R.;Ren, Rena Ning;Wu, Tsuei-Ju;Shen, Xiaolan;Lyons, Kathryn A.;Mao, An-Hua;Carlin, Josephine R.;Karanam, Bindhu V.;Vincent, Stella H.;Cheng, Kang;Goulet, Mark T. [Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,# 5,p. 827 - 832]

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