Triphenylmethyl chloride explained

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

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.^[1]

Reactions

Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium:

(C₆H₅)₃CCl + 2 Na → (C₆H₅)₃CNa + NaCl

Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate.

Trityl chloride reacts with zinc in nonpolar solvents (e.g. benzene) to form Gomberg's dimer.^[2]

2 (C₆H₅)₃CCl + Zn → ((C₆H₅)₃C)₂ + ZnCl₂

See also

• Triphenylmethyl radical
• Triphenylmethane
• Triphenylmethyl hexafluorophosphate
• Triphenylmethanol
• Gomberg's dimer

References

1. .
2. Gomberg . M. . An Instance of Trivalent Carbon: Triphenylmethyl . Journal of the American Chemical Society . 1900 . 22 . 11 . 757–771 . 10.1021/ja02049a006 .