Chlorotoluene

Chlorotoluene is a group of three isomeric chemical compounds. They (ortho-chlorotoluene, meta-chlorotoluene, and para-chlorotoluene) consist of a disubstituted benzene ring with one chlorine atom and one methyl group.

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.

Chlorotoluene isomers
General
Common name	o-chlorotoluene	m-chlorotoluene	p-chlorotoluene
Structure
Systematic name	1-chloro-2-methylbenzene	1-chloro-3-methylbenzene	1-chloro-4-methylbenzene
Molecular formula	C₇H₇Cl (C₆H₄ClCH₃)
Molar mass	126.586 g/mol
Appearance	colorless liquid
CAS number	[95-49-8]	[108-41-8]	[106-43-4]
Properties
Density and phase	1.073 g/ml, liquid	1.072 g/ml, liquid	1.069 g/ml, liquid
Solubility in water	practically insoluble
Other solubilities	Soluble in non-polar solvents such as aromatic hydrocarbons
Melting point	−35 °C (−31 °F; 238 K)	−47 °C (−52.6 °F; 226 K)	7 °C (44.6 °F; 280 K)
Boiling point	159 °C (318.2 °F; 432 K)	162 °C (323.6 °F; 435 K)	162 °C (323.6 °F; 435 K)
Magnetic susceptibility	-81.98 x 10⁻⁶ cm³/mol	-80.07 x 10⁻⁶ cm³/mol	-80.07 x 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.

Uses

2- and 4-Chlorotoluene are precursors to the corresponding benzyl chloride (ClC₆H₄CH₂Cl), benzaldehyde (ClC₆H₄CHO), and benzoyl chloride (ClC₆H₄C(O)Cl).[1]

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References

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.

CDC - NIOSH Pocket Guide to Chemical Hazards - o-Chlorotoluene

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[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.