Trichlorotoluene

This article is about compounds with chlorine atoms on the ring. For compounds with chlorine atoms on the methyl, see Benzotrichloride.

Trichlorotoluenes are organochlorine compounds, in particular aryl chlorides, with the formula CH3C6H2Cl3. Six constitutional isomers exist, differing in the relative position of the three chlorine substituents around the ring. All isomers colorless and lipophilic solids.

Trichlorotoluenes
Name 2,3,4-Trichlorotoluene 2,3,5-Trichlorotoluene 2,3,6-Trichlorotoluene 2,4,5-Trichlorotoluene 2,4,6-Trichlorotoluene 3,4,5-Trichlorotoluene
Structure
CAS Registry Number [7359-72-0] [56961-86-5] [2077-46-5] [6639-30-1] [23749-65-7] [21472-86-0]
Melting pt (°C) 42.9 44.65 42.95 79.95 32.0 44.85
Boiling pt (°C) 249.3 240.4 241.8 240.5 235.4 248.3

Preparation and use

Four trichlorotoluenes—the 2,3,4-, 2,3,6-, 2,4,5-, and 2,4,6- isomers—are produced in significant yields by treatment of toluene with three equivalents of chlorine in the presence of various Lewis acids.[1] These isomers result from the usual selectivity of electrophilic aromatic substitution reactions of substituted benzenes.

2,3,6-Trichlorotoluene is a precursor to 2,3,6-trichlorobenzoic acid (2,3,6-TBA), a commercial herbicide.

References

  1. ^ Beck, Uwe; Löser, Eckhard (2011). "Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o03. ISBN 978-3527306732.