Tetraiodoethylene

Tetraiodoethylene (TIE), or diiodoform, is the periodinated analogue of ethylene with the chemical formula C2I4. It is a decomposition product of carbon tetraiodide and diiodoacetylene.[5] It is an odourless yellow crystalline solid that is soluble in benzene and chloroform, and insoluble in water.[2] It has been used as an antiseptic and a component in pesticide and fungicide formulations.[6][7]

Tetraiodoethylene
Names
IUPAC name
tetraiodoethene
Other names
Periodoethylene, Periodoethene, Diiodoform, Ethylene tetraiodide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.434
EC Number
  • 208-176-2
UNII
  • InChI=1S/C2I4/c3-1(4)2(5)6
    Key: ZGQURDGVBSSDNF-UHFFFAOYSA-N
  • C(=C(I)I)(I)I
Properties
C2I4
Molar mass 531.640 g·mol−1
Appearance yellow crystalline solid
Odor Odourless[1]
Density 2.98
Melting point 187–192 °C (369–378 °F; 460–465 K)[2]
Boiling point Sublimates[2]
Insoluble
Solubility Soluble in chloroform, carbon disulphide, benzene and toluene[3]
Hazards
GHS labelling:[4]
GHS07: Exclamation mark
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetraiodoethylene reacts with ethylamine to give ethylamine di-tetraiodoethylene, EtNH2.(C2I4)2, and ethylaminetetraiodoethylene.[8] Tetraiodoethylene and iodine pentafluoride yield iodopentafluoroethane.[9]

Tetraiodoethylene turns brown and emits a "characteristic" odour due to decomposition when exposed to light.[10]

History

Tetraiodoethylene was discovered by Baeyer in 1885.[5] It was proposed as an antiseptic under the name Diiodoform, in 1893 by M. L. Maquenne and Taine.[10] It was an alternative to iodoform[10] which has a strong and persistent odour that caused difficulties for physicians in private practices.[11]

Synthesis

Tetraiodoethylene can be made by the iodination of calcium carbide:[1]

2 CaC2 + 5I2 → 2 C2I4 + 2 CaI

Diiodoacetylene is a byproduct of the reaction which can later be iodinated to TIE.[1]

The action of aqueous solution of potassium hydroxide and iodine on barium carbide in chloroform or benzene can also give TIE.[10] Another synthesis involves mixing separate solutions of diiodoacetylene and iodine in carbon disulphide. Tetraiodoethylene would be left as a residue after carbon disulphide was evaporated.[10]

See also

References

  1. TETRA-IODO-ETHYLENE, The Pharmaceutical Era. (1897). USA, D. O. Haynes & Company.
  2. Lide, D. R. (1995). CRC Handbook of Chemistry and Physics. (Special Student Edition): A Ready-Reference Book of Chemical and Physical Data. CRC-Press. Page 522
  3. Diiodoform in Notes on New Remedies. (1893). USA: Lehn & Fink.
  4. "Tetraiodoethylene". pubchem.ncbi.nlm.nih.gov.
  5. Peculiar Decomposition of Diiodoacetylene, Victor Meyel and Wilhelm Pemsel (1896)
  6. The Code of Federal Regulations of the United States of America (1984). U.S. Government Printing Office.
  7. Iodine and Plant Life: Annotated Bibliography, 1813-1949. With Review of the Literature. (1950). UK: Chilean Iodine Educational Bureau. page 22
  8. Action of Tetraiodoethylene on Organic Bases, Chemical Abstracts. (1912). American Chemical Society.
  9. Journal of the Chemical Society. (1948). page 2188
  10. New Remedies – Diiodoform in Merck's Market Report and Pharmaceutical Journal: An Independent Monthly Magazine Devoted to the Professional and Commercial Interests of the Druggist. (1894).
  11. Selections – DIIODOFORM in The International Dental Journal. (1895). USA: International Dental Publication Company.
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