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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.
Hazard Statements: H302-H312-H315-H319-H332-H335
Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant