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 of hydrogen atom. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalka ...

, sometimes used to introduce the trityl

protecting group A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In man ...

Preparation

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

acetyl chloride Acetyl chloride () 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 an ...

, or by the Friedel–Crafts alkylation of

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

with

carbon tetrachloride Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a n ...

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; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

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

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

. 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 = phenyl, 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 (chemi ...

.{{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, url-access=subscription :2 (C₆H₅)₃CCl + Zn → ((C₆H₅)₃C)₂ + ZnCl₂

References

Alkylating agents Organochlorides Phenyl compounds

Preparation

Reactions

See also

References