Carbon tetrabromide

• Catalog No.: L00821
• CAS Number: 558-13-4
• M. F.: CBr4
• M. W.: 331.6267
• Purity: 98% (dry wt.), may cont. up to ca 6% water

SYNONYMS

• Title: 四溴化碳
• IUPAC name: tetrabromomethane
• IUPAC Traditional name: carbon tetrabromide
• Synonyms: Tetrabromomethane

DATABASE IDS

• Beilstein Number: 1732799
• CAS Number: 558-13-4
• MDL Number: MFCD00000117
• EC Number: 209-189-6

PROPERTIES

• Purity: 98% (dry wt.), may cont. up to ca 6% water
• Boiling Point: 190°C
• Density: 3.420
• Melting Point: 90-95°C
• GHS Hazard statements: H318-H315-H302-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 22-37/38-41
• RTECS: FG4725000
• Safety Statements: 26-36/37/39-60
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2516
• Packing Group: III

REFERENCES

• 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 -111^o 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).