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Carbon tetrabromide is widely utilized as a solvent for greases, waxes and oils. In Appel reaction, it is used to convert alcohols to alkyl bromides. It has the property of non-flammability and finds application in fire-resistant chemicals as an active ingredient. It is also used for separating minerals. It can serves as an intermediate in manufacturing agrochemicals. It plays a vital role in the plastic and rubber industries for blowing and vulcanization.
Brominating agent for Li ester enolates, where bromine tends to give erratic results: J. Org. Chem., 43, 3687 (1978). Exchange reaction with n-BuLi or PhLi in ether at -111o generates tribromomethyllithium, giving 91% yield on carbonation: Chem. Ber., 101, 3230 (1968).
In combination with triphenylphosphine, effects the dibromomethylenation of aldehydes to 1,1-dibromoalkenes: J. Am. Chem. Soc., 84, 1745 (1962). Dehydrobromination of the products with n-BuLi provides a valuable aldehyde to alkyne homologation: Tetrahedron Lett., 3769 (1972); 31, 3141 (1990). An improved procedure, suitable for sensitive aldehydes, has been described using triethylamine in the dibromomethylenation step to suppress side reactions, and the hindered base sodium bis(trimethylsilylamide) (NaHMDS) for the elimination step: Tetrahedron Lett., 35, 3529 (1994); Synth. Commun., 25, 3641 (1995):
Also frequently used in combination with triphenylphosphine for the conversion of alcohols to alkyl bromides under mild conditions, applicable to sensitive substrates such as allylic or carbohydrate molecules: Chem. Ind. (London), 1017 (1969); J. Org. Chem., 36, 403 (1971); Synth. Commun., 24, 1117 (1994).
Sugiura, Y.; Tachikawa, Y.; Nagasawa, Y.; Tada, N.; Itoh, A. Synthesis of benzoyl cyanide through aerobic photooxidation of benzyl cyanide using carbon tetrabromide as a catalyst. RSC Adv. 2015, 5 (87), 70883-70886.
Choi, T.; Jung, H.; Lee, C. W.; Mun, K. Y.; Kim, S. H.; Park, J.; Kim, H. Growth characteristics of graphene synthesized via chemical vapor deposition using carbon tetrabromide precursor. Appl. Surf. Sci. 2015, 343, 128-132.
Gefahrenhinweise (EU): H302-H315-H318-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.