Carbon tetraiodide

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Carbon tetraiodide
Stereo, skeletal formula of carbon tetraiodide
Ball and stick model of carbon tetraiodide
Spacefill model of carbon tetraiodide
Names
IUPAC name
Tetraiodomethane[1]
Identifiers
507-25-5 N
1733108
ChemSpider 10055 YesY
EC number 208-068-5
Jmol-3D images Image
PubChem 10487
RTECS number FG4960000
Properties
CI4
Molar mass 519.63 g·mol−1
Appearance Dark violet crystals
Density 4.32 g mL−1
Structure
Tetragonal
Tetrahedral
0 D
Thermochemistry
0.500 J K−1 g−1
384.0–400.4 kJ mol−1
−794.4–−778.4 kJ mol−1
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H315, H319, H335
P261, P305+351+338
EU classification Irritant Xi
R-phrases R36/37/38
S-phrases S26, S36
Related compounds
Related alkanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Carbon tetraiodide is CI4, a tetrahalomethane. Being bright red, it is a relatively rare example of a highly colored methane derivative. It is only 2% by weight carbon, although other methane derivatives are known with still less carbon.

The tetrahedral molecule features C-I distances of 2.12 ± 0.02 Å.[2] The molecule is slightly crowded with short I---I contacts of 3.459 ± 0.03 Å, and possibly for this reason, it is thermally and photochemically unstable. Hexaiodoethane is unknown, probably for the same reason.

Carbon tetraiodide crystallizes in tetragonal crystal structure (a 6.409, c 9.558 (.10−1 nm)).[3]

It has zero dipole moment due to its symmetrically substituted tetrahedral molecule.

Properties, synthesis, uses[edit]

CI4 is slightly reactive towards water, giving iodoform and I2. Otherwise it is soluble in nonpolar organic solvents. It decomposes thermally and photochemically to tetraiodoethylene, I2C=CI2. Its synthesis entails AlCl3-catalyzed halide exchange, which is conducted at room temperature:[4]

CCl4 + 4 EtI → CI4 + 4 EtCl

The product crystallizes from the reaction solution.

CI4 is used as an iodination reagent, often upon reaction with base. [5] Ketones are converted to 1,1-diiodoethenes upon treatment with PPh3 and CI4. Alcohols are converted in and to iodide, by a mechanism similar to the Appel reaction. In an Appel reaction carbon tetrachloride is used to generate the chloride from alcohols.

Safety considerations[edit]

Manufacturers recommend that CI4 be stored near 0 °C (32 °F). As a ready source of iodine, it is an irritant. LD50: 178 mg.kg−1. In general, perhalogenated organic compounds should be considered toxic, with the narrow exception of small perfluoroalkanes (essentially inert due to the strength of the C-F bond).

References[edit]

  1. ^ "Tetraiodomethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 29 February 2012. 
  2. ^ Finbak, Chr.; Hassel, O. "Kristallstruktur und Molekülbau von CI4 und CBr4" Zeitschrift für Physikalische Chemie (1937), volume B36, page 301-8
  3. ^ Pohl, S. "Die Kristallstruktur von CI4" Zeitschrift für Kristallographie (1982), volume 159, page 211-216 http://www.oldenbourg-link.com/doi/abs/10.1524/zkri.1982.159.1-4.211
  4. ^ McArthur, R. E.; Simons, J. H., “Carbon Tetraiodide” Inorganic Syntheses 1950, volume III, 37–39
  5. ^ P. R. Schreiner, A. A. Fokin, “Carbon Tetraiodide” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2005; John Wiley & Sons, Ltd

Further reading[edit]

Sorros, H., Hinkam J. B., “The Redistribution Reaction. XI. Application to the Preparation of Carbon Tetraiodide and Related Halides” Journal of the American Chemical Society 1945, 67, 1643. DOI.