Chlorotriiodomethane

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Chlorotriiodomethane
Names
Preferred IUPAC name
Chloro(triiodo)methane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CClI3/c2-1(3,4)5
    Key: NHPRHZOZGKPNLB-UHFFFAOYSA-N
  • ClC(I)(I)I
Properties
CClI3
Molar mass 428.17 g·mol−1
Density 3.8 g/cm3
Boiling point 268.8 °C (515.8 °F; 542.0 K)
Hazards
Flash point 116.4±18.4 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlorotriiodomethane is a tetrahalomethane with the chemical formula CClI3.[1][2] This is a halomethane containing one iodine atom and three chlorine atoms attached to the methane backbone.[3]

Synthesis

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Chlorination of iodoform leads to chlorotriiodomethane.[4]

It can also be obtained by distilling trichloroacetyl chloride and hydrogen iodide at 140 °C, with hexachloroethane as a byproduct. Trichloromethane or carbon tetrachloride can also be reacted with iodine and sodium hydroxide at 0 °C to obtain the compound, but the yield is very low.[5]

References

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  1. ^ Comprehensive Organic Functional Group Transformations II: A Comprehensive Review of the Synthetic Literature 1995 - 2003. Elsevier. 16 December 2004. p. 3049. ISBN 978-0-08-052347-7. Retrieved 5 September 2025.
  2. ^ Luo, Yu-Ran (9 March 2007). Comprehensive Handbook of Chemical Bond Energies. CRC Press. p. 220. ISBN 978-1-4200-0728-2. Retrieved 5 September 2025.
  3. ^ "chlorotriiodomethane". NIST. Retrieved 5 September 2025.
  4. ^ Bartley, JP; Carman, RM; Russellmaynard, JKL (1985). "The Conversion of Primary and Aryl Iodides Into the Corresponding Chlorides". Australian Journal of Chemistry. 38 (12): 1879–1881. doi:10.1071/CH9851879.
  5. ^ Katritzky, A.R.; Gilchrist, T. L.; Meth-Cohn, O.; Rees, C. W. (1995). Comprehensive Organic Functional Group Transformations (1 ed.). Oxford: Elsevier Science. p. 221. ISBN 978-0-08-042704-1. Retrieved 4 September 2025.