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]
^Hartwell, Jonathan L. (1944). "o-Chlorobromobenzene". Organic Syntheses. 24: 22.
^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.
^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.
^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.
^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.
Bromochlorobenzenes are mixed aryl halides (aryl chloride and aryl bromide) consisting bromine and chlorine as substituents on a benzene ring. All three...
basis for chemoselectivity for nickel insertion into the C–Br bond of bromochlorobenzene using a NiCl2-based catalyst. The Kumada coupling is suitable for...