Triphenylmethane

Chemical properties

colorless or light brown powder. soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

The Uses of Triphenylmethane

Triphenylmethane is a triarylmethane compound used as the backbone of synthetic dyes. Triphenylmethane has also been shown to inhibit 3-methylcholanthrene-induced neoplastic transformation of 10T1/2 cells.

Definition

ChEBI: Triphenylmethane is a triarylmethane in which the three aryl groups are phenyl. It forms the basic skeleton of several synthetic dyes. It has a role as a xenobiotic and an environmental contaminant.

Preparation

Triphenylmethane can be synthesized by Friedel–Crafts reaction from benzene and chloroform with aluminium chloride catalyst:
3 C6H6 + CHCl3 → Ph3CH + 3 HCl

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 5846, 1951 DOI: 10.1021/ja01156a116
Organic Syntheses, Coll. Vol. 1, p. 548, 1941
Tetrahedron Letters, 21, p. 801, 1980 DOI: 10.1016/S0040-4039(00)71509-7

Purification Methods

Crystallise triphenylmethane from EtOH or *benzene (with one molecule of *benzene of crystallisation which is lost on exposure to air or by heating on a water bath). It can also be sublimed under vacuum. It has been given a preliminary purification by refluxing with tin and glacial acetic acid, then filtered hot through a glass sinter disc, and precipitated by addition of cold water. [Beilstein 5 H 698, 5 IV 2495.]