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558-13-4 - Carbon tetrabromide, 98% (dry wt.), may cont. up to ca 6% water - Tetrabromomethane - L00821 - Alfa Aesar

L00821 Carbon tetrabromide, 98% (dry wt.), may cont. up to ca 6% water

Codice CAS
558-13-4
Sinonimi
Tetrabromomethane

Dimensioni Prezzo ($) Quantità Disponibilità
25g 24,84
100g 53,25
500g 190,79
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Carbon tetrabromide, 98% (dry wt.), may cont. up to ca 6% water

MDL
MFCD00000117
EINECS
209-189-6

Proprietà chimiche

Formula
CBr4
Peso formula
331.63
Punto di fusione
90-95°
Punto di ebollizione
190°
Densità
3.420
Solubilità
Insoluble in water. Soluble in ether, chloroform and ethanol.

Applicazioni

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.

Note

Store in cool place. Incompatible with strong oxidizing agents, strong bases and lithium.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H318-H315-H302-H335

Causes serious eye damage. Causes skin irritation. Harmful if swallowed. May cause respiratory irritation.

Dichiarazioni precauzionali: P261-P280-P305+P351+P338-P304+P340-P310-P362-P301+P312-P312-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Immediately call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1732799
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2903.39
TSCA
Yes
RTECS
FG4725000

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