Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C
19H
15Cl. 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 ...
:
:(C
6H
5)
3CCl + 2 Na → (C
6H
5)
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.
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 ...
) 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 (C
6H
5)
3CCl + Zn → ((C
6H
5)
3C)
2 + ZnCl
2
See also
*
Triphenylmethyl radical
The triphenylmethyl radical (often shortened to trityl radical after 1927 suggestion by Burckhardt Helferich, Helferich et al.) is an organic compound with the formula (C6H5)3C. It is a persistent radical. It was the first radical (chemistry), rad ...
*
Triphenylmethane
Triphenylmethane or triphenyl methane (sometimes also known as Tritan), is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many syn ...
*
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 ...
*
Triphenylmethanol
*
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 ...
References
Alkylating agents
Organochlorides
Phenyl compounds