10355. Triphosgene

Nomenclature

CAS number: 32315-10-9
1,1,1-Trichloromethanol 1,1′-carbonate; bis(trichloromethyl) carbonate; hexachlorodimethyl carbonate; trichloromethyl carbonate; BTC.
C3Cl6O3; mol wt 296.75.
C 12.14%, Cl 71.68%, O 16.17%.

Description and references

Versatile substitute for phosgene, q.v.; reagent used for oxidations, chlorinations, and nucleophilic substitutions. Prepn: C. Councler, Ber. 13, 1696 (1880); and synthetic applications: H. Eckert, B. Forster, Angew. Chem. Int. Ed. Engl. 26, 894 (1987) DOI. Additional synthetic applications: M. J. Coghlan, B. A. Caley, Tetrahedron Lett. 30, 2033 (1989) DOI; C. Palomo et al., J. Org. Chem. 56, 5948 (1991) DOI; R. Wilder, S. Mobashery, ibid. 57, 2755 (1992) DOI. Crystal structure: A. M. Sorenson, Acta Chem. Scand. 25, 169 (1971) DOI. Reviews: L. Cotarca et al., Synthesis 1996, 553-576 DOI; W. Su et al., Org. Prep. Proced. Int. 36, 499-547 (2004).

Chemical structure

Properties

White crystalline solid, mp 81-83°. bp760 203°; bp50 124°; bp36 117°; bp22 105°. Poisonous. Corrosive. Lachrymator. d 1.78; d (calc) 2.01; d80 1.629. Sol in methanol, ethanol, benzene, diethyl ether, hexane, tetrahydrofuran, ethyl acetate, chloroform. Dec slowly in cold water.

Use

Reagent in synthetic organic chemistry.