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Benzyltrimethylammonium Tribromide

Benzyltrimethylammonium tribromide (BTMA-Br₃) can be used as a replacement for liquid elemental bromine, a highly toxic and corrosive reagent. For small scale reactions it is difficult to add a stocichiometric amount of bromine. BTMA-Br₃ is a crystalline solid that can be conveniently weighed out for use in small scale synthesis work.
BTMA-Br₃ has been used for the oxidation of sulfides to sulfoxides¹.

BTMA-Br₃ is a convenient reagent for the conversion of aryl thioureas to 2-aminobenzothiazoles².

These same authors also developed a one-pot synthesis of 2-aminobenzothiazoles from either aryl isothiocyanates and amines or Bu₄N⁺ NCS^- and anilines using BTMA-Br_3.
BTMA-Br₃ has also been used for the oxidation of aldehydes³,diols⁴ and alcohols⁵.
Bromination of alkenes proceeds smoothly with BTMA-Br₃ in aprotic solvents⁶.

Kowalski, P.; Mitka, K.; Ossowska, K.; Kolarska, Z. Tetrahedron,  2005, 61, 1933.

1. Jordan, A.; Luo, C.; Reitz, A. JOC,  2003, 68, 8693
2. Goswami, G.; Kothari, S.; Banerji, K. J. Chem. Research, 1999, 176.
3. Goswami, G.; Kothari, S.; Banerji, K. Proc. Indian Acad. Sci., 2001, 113, 43.
4. Kajigaeshi, S.; Kawamukai, H.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1989, 62, 2585.
5. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Fujisaki, S.; Tashiro, M. Rep. Inst. Advanced Material Study, 1988, 2, 87.