10366. Trityl Chloride

Nomenclature

CAS number: 76-83-5
1,1′,1″-(Chloromethylidyne)trisbenzene; chlorotriphenylmethane; triphenylchloromethane; triphenylmethyl chloride; TPCM.
C19H15Cl; mol wt 278.78.
C 81.86%, H 5.42%, Cl 12.72%.

Description and references

Reagent for the introduction of the triphenylmethyl (trityl) protecting group, commonly used to protect alcohols as trityl ethers. Prepn: W. Hemilian, Ber. 7, 1203 (1874); W. E. Bachmann, Org. Synth. coll. vol. III, 841 (1955). Crystal structure analysis: R. Gerdil, A. Dunand, Acta Crystallogr. B31, 936 (1975) DOI; A. Dunand, R. Gerdil, ibid. B38, 570 (1982) DOI. Polymorphism studies: A. H. Brunetti, Solid State Nuc. Magn. Reson. 25, 167 (2004) DOI PubMed. Hydroxyl group protection: S. K. Chaudhary, O. Hernandez, Tetrahedron Lett. 20, 95 (1979) DOI; S. Colin-Messager et al., ibid. 33, 2689 (1992) DOI. Additional synthetic applications: M. S. Newman, C. H. Chen, J. Am. Chem. Soc. 95, 278 (1973) DOI; A. Khalafi-Nezhad et al., Synthesis 2008, 617 DOI.

Chemical structure

Properties

Colorless crystals, mp 111-112°. bp20 230-235°. d 1.26. Corrosive. Lachrymator. Sol in most organic solvents. Moisture sensitive.

Use

Reagent and catalyst in synthetic organic chemistry.