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

Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction...

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Preparation

Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol

Triphenylmethanol

Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene...

 with acetyl chloride

Acetyl chloride

Acetyl chloride, CH3COCl, also known as ethanoyl chloride or acyl chloride, is an acid chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless liquid. Acetyl chloride does not exist in nature, because contact with water would hydrolyze...

, or by the Friedel-Crafts alkylation of benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 with carbon tetrachloride

Carbon tetrachloride

Carbon tetrachloride, also known by many other names is the organic compound with the formula CCl4. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, and as a cleaning agent...

 to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed.

Reactions

Triphenylmethylsodium may can be prepared from trityl chloride and sodium

Sodium

Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...

:₃CCl + 2 Na → (C₆H₅)₃CNa + NaCl
Reaction with silver hexafluorophosphate

Silver hexafluorophosphate

Silver hexafluorophosphate, sometimes referred to "silver PF-6," is an inorganic compound with the formula AgPF6.-Uses and reactions:Silver hexafluorophospate is a commonly encountered reagent in inorganic and organometallic chemistry...

 gives triphenylmethyl hexafluorophosphate

Triphenylmethyl hexafluorophosphate

Triphenylmethyl hexafluorophosphate is an organic salt with the formula C3PF6. This compound is a brown powder that is air sensitive and changes colors when exposed to light. Triphenylmethyl hexafluorophosphate is used as a catalyst and reagent in organic syntheses.-Preparation:Triphenylmethyl...

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