Trichlorotoluene

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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.

Contents

Trichlorotoluenes
Name2,3,4-Trichlorotoluene2,3,5-Trichlorotoluene2,3,6-Trichlorotoluene2,4,5-Trichlorotoluene2,4,6-Trichlorotoluene3,4,5-Trichlorotoluene
Structure 2,3,4-Trichlorotoluene.svg 2,3,5-Trichlorotoluene.svg 2,3,6-Trichlorotoluene.svg 2,4,5-Trichlorotoluene.svg 2,4,6-Trichlorotoluene.svg 3,4,5-Trichlorotoluene.svg
CAS Registry Number [7359-72-0][56961-86-5][2077-46-5][6639-30-1][23749-65-7][21472-86-0]
Melting pt (°C)42.944.6542.9579.9532.044.85
Boiling pt (°C)249.3240.4241.8240.5235.4248.3

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.

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<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

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<span class="mw-page-title-main">Trichlorobenzene</span>

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6
H
6
Cl
6
, is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to each carbon. This structure has nine stereoisomers, which differ by the stereochemistry of the individual chlorine substituents on the cyclohexane. It is sometimes erroneously called "benzene hexachloride" (BHC). They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. The isomers are poisonous, pesticidal, and persistent organic pollutants, to varying degrees.

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Dichlorotoluenes are organochlorine compounds, in particular aryl chlorides, with the formula CH3C6H3Cl2. Six constitutional isomers exist, differing in the relative position of the two chlorine substituents around the ring. They are all colorless and lipophilic. The 3,5 isomer is a solid at room temperature, whereas the others are liquids.

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.