Bromochlorobenzene Explained

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

align="center" colspan="4"	Isomers of Bromochlorobenzene
Skeletal formula
align="center" colspan="4"	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
Appearance at room temperature and pressure
CAS number
ChemSpider

align="center" colspan="4"	Properties
Density and phase	g/cm³, solid	g/cm³, liquid	g/cm³, liquid
Solubility in pure water at 20−25 °C	g/100 ml	g/100 ml	g/100 ml
Other solvents e.g. ethanol, acetone -->	solubility info on other solvents -->	- -->	Melting point	-13°C	-22°C	NaN°C
Boiling point	NaN°C	NaN°C	196°C
align="center" colspan="4"	Structure
Dipole moment	D	D	D-->

All three have been synthesized by various routes:

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

Notes and References

10.1021/jo00380a031. Use of aryltrimethylgermanium substrates for facile aromatic chlorination, bromination, and iodination. The Journal of Organic Chemistry. 52. 4. 664–667. 1987. Moerlein. S. M..
10.1246/cl.1981.243. 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. 1981. Hosomi. Akira. Iijima. Susumu. Sakurai. Hideki.
10.1021/ja01059a073. 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. 1964. Wiley. G. A.. Hershkowitz. R. L.. Rein. B. M.. Chung. B. C..
10.1021/jo00297a087. Preparation of aryl chlorides from phenols. The Journal of Organic Chemistry. 55. 10. 3415–3417. 1990. Bay. Elliott. Bak. David A.. Timony. Peter E.. Leone-Bay. Andrea.