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Chlorotoluene

Group of ortho, meta, para isomers

Group of ortho, meta, para isomers

Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–nCln, where n = 1–5 is the number of chlorine atoms.

Monochlorotoluene

Monochlorotoluenes are chlorotoluenes containing one chlorine atom. There are three isomers, each with the formula C7H7Cl.

Properties

The isomers differ in the location of the chlorine, but have the same chemical formula. All have very similar boiling points, although p-chlorotoluene has a much higher melting point due to a more tightly packed crystal structure.

Monochlorotoluene isomersProperties
Common name
Structure[[File:o-Chlortoluol.svg90px]]
Systematic name1-chloro-2-methylbenzene
Molecular formulaC7H7Cl (C6H4ClCH3)
Molar mass126.586 g/mol
Appearancecolorless liquid
CAS number[95-49-8]
Density and phase1.073 g/ml, liquid
Solubility in waterpractically insoluble
Other solubilitiesSoluble in non-polar solvents such as aromatic hydrocarbons
Melting point−35 °C (−31 °F; 238 K)
Boiling point159 °C (318.2 °F; 432 K)
Magnetic susceptibility−81.98·10−6 cm3/mol

Benzyl chloride is an isomer, which has a chlorine substituted for one of the hydrogens of toluene's methyl group, and it is sometimes named α-chlorotoluene.

Preparation

A laboratory route to 2- and 4-chlorotoluene proceeds from 2- and 4-toluidines (i.e. 2- and 4-aminotoluene). These compounds are diazotized followed by treatment with cuprous chloride. Industrially, the diazonium method is reserved for 3-chlorotoluene. The industrial route to 2- and 4-chlorotoluene entails direct reaction of toluene with chlorine. The more valuable 4-chlorotoluene is separated from 2-chlorotoluene by distillation. Distillation cannot be applied to separating 3-chlorotoluene from 4-chlorotoluene.

Uses

2- and 4-chlorotoluene are precursors to the corresponding benzyl chloride (ClC6H4CH2Cl), benzaldehyde (ClC6H4CHO), and benzoyl chloride (ClC6H4C(O)Cl). Chlorotoluenes are precursors to dichlorotoluenes.

References

References

  1. C. S. Marvel and S. M. McElvain. (1923). "o-Chlorotoluene and p-Chlorotoluene". Organic Syntheses.
  2. (2011). "Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons".
  3. (2000). "Nitriles".
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chlorobenzene-derivatives toluenes multiple-compounds,-tabular
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