Trichloroiodomethane

Trichloroiodomethane
Identifiers
3D model (JSmol)	Interactive image;
	SMILES IC([Cl])([Cl])[Cl];
Properties
Chemical formula	CCl3I
Molar mass	245.27 g·mol−1
Appearance	Pale orange liquid
Boiling point	142 °C (288 °F; 415 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trichloroiodomethane is a tetrahalomethane with the chemical formula CCl₃I. It contains one chlorine and three iodine atoms attached to a central carbon atom.

Despite its relative simplicity, trichloroiodomethane was not commercially available as of 2015.^[3]

Like other iodinated tetrahalomethanes, trichloroiodomethane decomposes easily, releasing iodine,^[2] The iodine atom is susceptible to halogen bonds; CCl₃I forms 1:1 adducts with pnictogen bases.^[1]

It is the minor product of chloroform oxidation with sodium hypoiodite (the major product being dichloroiodomethane),^[4] but can be produced efficiently through electrophilic substitution between carbon tetrachloride and aluminum iodide.^[1]

References

1 2 3 Pullman, B. J.; West, B. O. (1961) [14 Nov 1960]. "The reaction of trichloroiodomethane with some organometallic compounds of group VB elements". J. Inorg. Nucl. Chem. 19. Northern Ireland: Pergamon: 262–271. doi:10.1016/0022-1902(61)80115-2.
1 2 Mann, Richard H.; Manis, Peter M. (1973) [June 20, 1972]. "A vibrational analysis of trichloroiodomethane". Journal of Molecular Spectroscopy. 45. Academic Press: 65–70. doi:10.1016/0022-2852(73)90175-6.
↑ Chemical evaluation of drinking water disinfection byproducts (Report). Agencia Estatal Consejo Superior de Investigaciones Cientificas. 24 July 2015.
↑ Kennedy, John Rider; Vickrey, Thomas M.; G. R. Somayajulu; Zwolinski, Bruno J. (1979). "Synthesis of CHCl₂I, CCl₃I, CHBr₂I, and CBr₃I". Journal of Chemical and Engineering Data. 24 (3). American Chemical Society: 251. doi:10.1021/je60082a003.

[Adduct-1] 1 2 3 Pullman, B. J.; West, B. O. (1961) [14 Nov 1960]. "The reaction of trichloroiodomethane with some organometallic compounds of group VB elements". J. Inorg. Nucl. Chem. 19. Northern Ireland: Pergamon: 262–271. doi:10.1016/0022-1902(61)80115-2.

[REU-2] 1 2 Mann, Richard H.; Manis, Peter M. (1973) [June 20, 1972]. "A vibrational analysis of trichloroiodomethane". Journal of Molecular Spectroscopy. 45. Academic Press: 65–70. doi:10.1016/0022-2852(73)90175-6.

[3] Chemical evaluation of drinking water disinfection byproducts (Report). Agencia Estatal Consejo Superior de Investigaciones Cientificas. 24 July 2015.

[4] Kennedy, John Rider; Vickrey, Thomas M.; G. R. Somayajulu; Zwolinski, Bruno J. (1979). "Synthesis of CHCl₂I, CCl₃I, CHBr₂I, and CBr₃I". Journal of Chemical and Engineering Data. 24 (3). American Chemical Society: 251. doi:10.1021/je60082a003.

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