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 Edit this at Wikidata
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).

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

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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

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

CaC2 + 3I2 → C2I4 + CaI2

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

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References

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  1. ^ a b c TETRA-IODO-ETHYLENE, The Pharmaceutical Era. (1897). USA, D. O. Haynes & Company.
  2. ^ a b c 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. ^ a b Diiodoform in Notes on New Remedies. (1893). USA: Lehn & Fink.
  4. ^ "Tetraiodoethylene". pubchem.ncbi.nlm.nih.gov.
  5. ^ a b 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. ^ a b c d e 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.