10211. Trifluoroiodomethane

Nomenclature

CAS number: 2314-97-8
Iodotrifluoromethane; trifluoromethyl iodide.
CF3I; mol wt 195.91.
C 6.13%, F 29.09%, I 64.78%.

Description and references

Non-ozone depleting gas with very low global warming potential. Prepn from IF5 and CCl4: A. A. Banks et al., J. Chem. Soc. 1948, 2188 DOI; from silver trifluoroacetate and iodine: A. L. Henne, W. G. Finnegan, J. Am. Chem. Soc. 72, 3806 (1950) DOI; from ZnBr(CF3).2DMF and ICl: D. Naumann et al., J. Fluorine Chem. 67, 91 (1994) DOI; from CHF3 and I2: N. Nagasaki et al., Catal. Today 88, 121 (2004) DOI. Physical properties: E. A. Nodiff et al., J. Org. Chem. 18, 235 (1953) DOI. Microwave spectrum: A. P. Cox et al., J. Chem. Soc. Faraday Trans. 2 76, 339 (1980) DOI. Powder neutron diffraction structure: S. J. Clarke et al., Z. Kristallogr. 206, 87 (1993). Raman spectra: A. J. Beardsall et al., J. Raman Spectrosc. 25, 761 (1994) DOI. Spectroscopic evaluation of ozone depletion and global warming potentials: S. Solomon et al., J. Geophys. Res. 99, 20929 (1994) DOI. Thermal decompn: S. S. Kumaran et al., Chem. Phys. Lett. 243, 59 (1995) DOI. 19F- and 13C-NMR spectra: W. Tyrra et al., Z. Anorg. Allg. Chem. 623, 1857 (1997) DOI. Thermodynamic properties: Y. Y. Duan et al., Int. J. Thermophys. 21, 393 (2000) DOI. FTIR spectroscopy: S. M. Webb et al., J. Quant. Spectrosc. Radiat. Transfer 94, 425 (2005) DOI. Use as a dielectric etchant: R. A. Levy et al., J. Mater. Res. 13, 2643 (1998) DOI. Synthetic use with tetrakis(dimethylamino)ethylene as a trifluoromethylation reagent: W. Xu, W. R. Dolbier, Jr., J. Org. Chem. 70, 4741 (2005) DOI PubMed.

Properties

bp760 22.5°. mp ≈130°. d478.5 2.5485. d432.5 2.3608. nD29.8 1.3710. nD42.2 1.3790. Misc with mineral oil; compat with materials of refrigeration systems. Light sensitive.

Use

Trifluoromethylating agent in organic synthesis; etchant gas; halon alternative in fire extinguishers and refrigerant applications.