Chlorofluoroiodomethane

Last updated
Chlorofluoroiodomethane
CHFClI.png
Names
Preferred IUPAC name
Chloro(fluoro)iodomethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/CHClFI/c2-1(3)4/h1H
    Key: HLSRAOHMHGINPN-UHFFFAOYSA-N
  • C(F)(Cl)I
Properties
CHClFI
Molar mass 194.37 g·mol−1
AppearanceLight yellow liquid
Density 2.4 g/cm³
Boiling point 76.1 °C (169.0 °F; 349.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlorofluoroiodomethane is a trihalomethane with the chemical formula CHClFI. [1] This complex organic compound is characterized by having three halogen atoms—fluorine, chlorine, and iodine—bonded to a methane backbone. The molecule is chiral. [2] [3]

Contents

Synthesis

The compound can be obtained by reacting dichloromethane with mercury fluoride. [4] Also, by heating dry (+)- strychnine fluorochloroiodoacetate at 100 mmHg and 110 °C can produce (+)-chlorofluoroiodomethane. [5]

Uses

Chlorofluoroiodomethane serves as a potentially important reagent in organic synthesis, especially for the transfer of halogenated methyl groups. Its three distinct carbon-halogen bonds exhibit varied reactivity, rendering it a flexible precursor for assembling more complex molecular structures. [6]

References

  1. ↑ Informatics, NIST Office of Data and. "chlorofluoroiodomethane". NIST . Retrieved 31 August 2025.
  2. ↑ Cuisset, A.; Aviles Moreno, J. R.; Huet, T. R.; Petitprez, D.; Demaison, J.; Crassous, J. (1 June 2005). "The Chiral Molecule CHClFI: First Determination of Its Molecular Parameters by Fourier Transform Microwave and Millimeter-Wave Spectroscopies Supplemented by ab Initio Calculations". The Journal of Physical Chemistry A . 109 (25): 5708–5716. Bibcode:2005JPCA..109.5708C. doi:10.1021/jp0443658. ISSN   1089-5639. PMID   16833903 . Retrieved 31 August 2025.
  3. ↑ Soulard, Pascale; Asselin, Pierre; Cuisset, Arnaud; Moreno, Juan Ramon Aviles; Huet, Thérèse R.; Petitprez, Denis; Demaison, Jean; Freedman, Teresa B.; Cao, Xiaolin; Nafie, Laurence A.; Crassous, Jeanne (15 December 2006). "Chlorofluoroiodomethane as a potential candidate for parity violation measurements". Physical Chemistry Chemical Physics . 8 (1): 79–92. Bibcode:2006PCCP....8...79S. doi:10.1039/B510675C. ISSN   1463-9084. PMID   16482247 . Retrieved 31 August 2025.
  4. ↑ Li, Dong Bo; Ng, Siu-Choon; Novak, Igor (15 July 2002). "Novel synthetic approaches to CHBrFI, CHClFI and CHBrClI". Tetrahedron . 58 (29): 5923–5926. doi:10.1016/S0040-4020(02)00532-X. ISSN   0040-4020 . Retrieved 31 August 2025.
  5. ↑ Crassous, Jeanne; Jiang, Zhengjin; Schurig, Volker; Polavarapu, Prasad L. (5 July 2004). "Preparation of (+)-chlorofluoroiodomethane, determination of its enantiomeric excess and of its absolute configuration". Tetrahedron: Asymmetry. 15 (13): 1995–2001. doi:10.1016/j.tetasy.2004.06.006. ISSN   0957-4166 . Retrieved 31 August 2025.
  6. ↑ "Methane, chlorofluoroiodo- (1512-28-3) for sale". vulcanchem.com. Retrieved 31 August 2025.
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