Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, 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.[3]
Reactions
Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium:[4]
- (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.[5]
- 2 (C6H5)3CCl + Zn → ((C6H5)3C)2 + ZnCl2
See also
- Triphenylmethyl radical
- Triphenylmethane
- Triphenylmethyl hexafluorophosphate
- Triphenylmethanol
- Gomberg's dimer
References
- ^ "Archived copy". Archived from the original on 2013-01-24. Retrieved 2014-01-08.
{{cite web}}: CS1 maint: archived copy as title (link) - ^ "Trityl chloride | CAS 76-83-5".
- ^ W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955). "Triphenylchloromethane". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 3, p. 841.. - ^ W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses; Collected Volumes, vol. 2, p. 607.
- ^ Gomberg, M. (1900). "An Instance of Trivalent Carbon: Triphenylmethyl". Journal of the American Chemical Society. 22 (11): 757–771. doi:10.1021/ja02049a006.
Recent Comments