Chlorodifluoroiodomethane

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Chlorodifluoroiodomethane
Names
Preferred IUPAC name
Chloro(difluoro)iodomethane
Other names
Difluorochloroiodomethane, chloro-difluoro-iodomethane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CClF2I/c2-1(3,4)5
    Key: CDNQVRRPSZBJQC-UHFFFAOYSA-N
  • C(F)(F)(Cl)I
Properties
CClF2I
Molar mass 212.36 g·mol−1
Density 2.5 g/cm³
Boiling point 34.6 °C (94.3 °F; 307.8 K)
Hazards
Flash point -25.3 °C
Related compounds
Related compounds
 Chlorofluoroiodomethane; Dichlorofluoroiodomethane; Chlorofluorodiiodomethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlorodifluoroiodomethane is a tetrahalomethane with the chemical formula CClF2I.[1][2] This is a halomethane containing two fluorine atoms, one chlorine atom, and one iodine atom attached to the methane backbone.[3]

Synthesis

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It can be prepared by reacting methyl difluorochloroacetate, LiCl/HMPA, and iodine or iodine monobromide at 90–95 °C, or by reacting silver difluorochloroacetate and iodine at 120–260 °C:[4]

CClF2COOAg + I2 → CClF2I + CO2 + AgI

The compound can also be obtained by the inductively coupled plasma (12 MHz) reaction of hexafluoroethane or trifluorochloromethane with iodine.[5] Other methods are also known.[6]

References

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  1. ^ Luo, Yu-Ran (9 March 2007). Comprehensive Handbook of Chemical Bond Energies. CRC Press. p. 244. ISBN 978-1-4200-0728-2. Retrieved 4 September 2025.
  2. ^ "Chlorodifluoroiodomethane". NIST. Retrieved 4 September 2025.
  3. ^ Frenkel, Michael; Kabo, G. J.; Marsh, K. N.; Roganov, G. N.; Wilhoit, R. C. (15 June 1994). Thermodynamics of Organic Compounds in the Gas State. CRC Press. ISBN 978-1-883400-04-0. Retrieved 4 September 2025.
  4. ^ Katritzky, A.R.; Gilchrist, T. L.; Meth-Cohn, O.; Rees, C. W. (1995). Comprehensive Organic Functional Group Transformations (1. ed.). Oxford: Elsevier Science. p. 224. ISBN 978-0-08-042704-1. Retrieved 4 September 2025.
  5. ^ Schmeisser, M.; Heuser, W.; Danzmann, E. (1976). "ChemInform Abstract: PREPARATION OF TRIFLUOROIODOMETHANE, BROMOTRIFLUOROMETHANE, AND TRIFLUORONITROSOMETHANE BY CHEMICAL PLASMA". Chemischer Informationsdienst (in German). 7 (2) chin.197602127. doi:10.1002/chin.197602127. ISSN 2199-2924. Retrieved 4 September 2025.
  6. ^ Comprehensive Organic Functional Group Transformations II: A Comprehensive Review of the Synthetic Literature 1995 - 2003. Elsevier. 16 December 2004. p. 3050. ISBN 978-0-08-052347-7. Retrieved 4 September 2025.