Bromochlorobenzene

Bromochlorobenzenes are mixed aryl halides (aryl chloride and aryl bromide) consisting bromine and chlorine as substituents on a benzene ring.

Isomers of Bromochlorobenzene
Skeletal formula
General
Common names	o-bromochlorobenzene ortho-bromochlorobenzene	m-bromochlorobenzene meta-bromochlorobenzene	p-bromochlorobenzene para-bromochlorobenzene
Systematic name	1-bromo-2-chlorobenzene	1-bromo-3-chlorobenzene	1-bromo-4-chlorobenzene
Molecular formula	BrC6H4Cl
Molar mass	191.45 g/mol
CAS number	694-80-4	108-37-2	106-39-8
ChemSpider	12230	13875377	7518
PubChem CID	12754	7928	7806
Properties
Melting point	−13 °C (260 K)	−22 °C (251 K)	63–67 °C (336–340 K)
Boiling point	203–205 °C (476–478 K)	195–196 °C (468–469 K)	196 °C (469 K)

All three have been synthesized by various routes:

• 1-Bromo-2-chlorobenzene: from 2-chloroaniline, via diazotization followed by a Sandmeyer reaction^[1]
• 1-Bromo-3-chlorobenzene: by (3-chlorophenyl)trimethylgermanium by electrophilic substitution^{[2][better source needed]}
• 1-Bromo-4-chlorobenzene:
  • From a derivative of (4-bromophenyl)silane using N-bromosuccinimide^[3]
  • From 4-chlorophenol using triphenylphosphine dibromide^[4] or phenylphosphorus tetrachloride^[5]

See also

• Bromoiodobenzene

References

1. Hartwell, Jonathan L. (1944). "o-Chlorobromobenzene". Organic Syntheses. 24: 22.
2. Moerlein, S. M. (1987). "Use of aryltrimethylgermanium substrates for facile aromatic chlorination, bromination, and iodination". The Journal of Organic Chemistry. 52 (4): 664–667. doi:10.1021/jo00380a031.
3. Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki (1981). "Carbon–silicon bond cleavage of organotrialkoxysilanes and organosilatranes with m-chloroperbenzoic acid and N-bromosuccinimide. New route to phenols, primary alcohols and bromides". Chemistry Letters. 10 (2): 243–246. doi:10.1246/cl.1981.243.
4. Wiley, G. A.; Hershkowitz, R. L.; Rein, B. M.; Chung, B. C. (1964). "Studies in Organophosphorus Chemistry. I. Conversion of Alcohols and Phenols to Halides by Tertiary Phosphine Dihalides". Journal of the American Chemical Society. 86 (5): 964–965. doi:10.1021/ja01059a073.
5. Bay, Elliott; Bak, David A.; Timony, Peter E.; Leone-Bay, Andrea (1990). "Preparation of aryl chlorides from phenols". The Journal of Organic Chemistry. 55 (10): 3415–3417. doi:10.1021/jo00297a087.