Toluene

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−93 °C

110.6 °C

Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. Chemically it is a mono-substituted benzene derivative, i.e. one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.

It is an aromatic hydrocarbon that is widely used as an industrial feedstock and as a solvent. Like other solvents, toluene is sometimes also used as an inhalant drug for its intoxicating properties; however, this can potentially cause severe neurological harm.[1][2]

Contents

History

The name toluene was derived from the older name toluol, which refers to tolu balsam, an aromatic extract from the tropical Colombian tree Myroxylon balsamum, from which it was first isolated. It was originally named by Jöns Jakob Berzelius.

Chemical properties

Toluene reacts as a normal aromatic hydrocarbon towards electrophilic aromatic substitution.[3][4][5] The methyl group makes it around 25 times more reactive than benzene in such reactions. It undergoes smooth sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene. It undergoes nitration to give ortho and para nitrotoluene isomers, but if heated it can give dinitrotoluene and ultimately the explosive trinitrotoluene (TNT).

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