Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C₁₉H₁₅Cl. It is an

alkyl halide The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely ...

, sometimes used to introduce the trityl protecting group.

Preparation

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

triphenylmethanol Triphenylmethanol (also known as triphenylcarbinol, TrOH) 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. In strongly acidic solutions ...

with

acetyl chloride Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On a ...

, or by the Friedel–Crafts alkylation of

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

with

carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...

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

Reactions

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

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...

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

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

gives

triphenylmethyl hexafluorophosphate Triphenylmethyl (also triphenylcarbenium, trityl, or tritylium) hexafluorophosphate is an organic salt with the formula or , consisting of the triphenylmethyl cation and the hexafluorophosphate anion . Triphenylmethyl hexafluorophosphate is a ...

. Trityl chloride reacts with zinc in nonpolar solvents (e.g.

) to form

Gomberg's dimer Gomberg's dimer is the organic compound with the formula Ph2C=C6H5-CPh3, where Ph = C6H5. It is a yellow solid that is air-stable for hours at room temperature and soluble in organic solvents. The compound achieved fame as the dimer of triphenylm ...

.{{cite journal , last1=Gomberg , first1=M. , title=An Instance of Trivalent Carbon: Triphenylmethyl , journal=Journal of the American Chemical Society , date=1900 , volume=22 , issue=11 , pages=757–771 , doi=10.1021/ja02049a006 , url=https://pubs.acs.org/doi/abs/10.1021/ja02049a006 :2 (C₆H₅)₃CCl + Zn → ((C₆H₅)₃C)₂ + ZnCl₂

References

Alkylating agents Organochlorides Phenyl compounds

Preparation

Reactions

See also

References