Triphenylmethyl chloride or trityl chloride (TrCl) is an organic compound with the chemical formula (C6H5)3CCl. It is a white solid although impure samples can appear yellowish. It is 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.
Reactions Triphenylmethylsodium can be prepared from trityl chloride 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 (C6H5)3CCl + Zn → [(C6H5)3C]2 + ZnCl2
See also Triphenylmethyl radical Triphenylmethane Triphenylmethyl hexafluorophosphate Triphenylmethanol Gomberg's dimer
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