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Triphenylmethyl Chloride: A Comprehensive Overview

Oct 21，2024

Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide commonly used in organic synthesis to introduce the trityl protecting group.

Article illustration

Triphenylmethyl chloride is used in the preparation of S-trityl-L-cysteine (STLC), a tight-binding inhibitor of Eg5 that prevents mitotic progression.

Preparation

Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed.

References:

[1] FONKEN G J. Alkylation of Benzene with Triphenylmethyl Chloride[J]. Journal of Organic Chemistry, 1963, 28 7: 3A - 1948. DOI:10.1021/jo01042a510.

[2] BILL B. SMITH J E L. The Behavior of Triphenylmethyl Chloride in Nitromethane[J]. Journal of the American Chemical Society, 1955, 77 6: 1397-1714. DOI:10.1021/ja01611a101.

[3] C. GARDNER SWAIN E E P. Mechanism of Methanolysis of Triphenylmethyl Chloride in Benzene Solution1-3[J]. Journal of the American Chemical Society, 1958, 80 4: 761-1014. DOI:10.1021/ja01537a016.