Chlorodifluoroiodomethane

Chlorodifluoroiodomethane

Names
Preferred IUPAC name Chloro(difluoro)iodomethane
Other names Difluorochloroiodomethane Chloro-difluoro-iodomethane
Identifiers
CAS Number	420-49-5  Y
3D model (JSmol)	Interactive image
ChemSpider	10752007
PubChem CID	22016178
InChI InChI=1S/CClF2I/c2-1(3,4)5 Key: CDNQVRRPSZBJQC-UHFFFAOYSA-N
SMILES C(F)(F)(Cl)I
Properties
Chemical formula	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). Infobox references

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

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

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.