Tetraiodoethylene, TIE or diiodoform, is an organoiodine compound with the chemical formula . Its structure is . It is an odourless yellow crystalline solid that is soluble in benzene and chloroform, and insoluble in water.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 It has been used as an antiseptic and a component in pesticide and fungicide formulations.The Code of Federal Regulations of the United States of America (1984). U.S. Government Printing Office.Iodine and Plant Life: Annotated Bibliography, 1813-1949. With Review of the Literature. (1950). UK: Chilean Iodine Educational Bureau. page 22 It is the periodinated analogue of ethylene. It is a decomposition product of carbon tetraiodide and diiodoacetylene.Peculiar Decomposition of Diiodoacetylene, Victor Meyel and Wilhelm Pemsel (1896)
Tetraiodoethylene reacts with ethylamine to give ethylamine di-tetraiodoethylene, , and ethylamine tetraiodoethylene, .Action of Tetraiodoethylene on Organic Bases, Chemical Abstracts. (1912). American Chemical Society. Tetraiodoethylene and iodine pentafluoride yield iodopentafluoroethane.Journal of the Chemical Society. (1948). page 2188
Tetraiodoethylene turns brown and emits a characteristic odour due to decomposition when exposed to light.
History Tetraiodoethylene was discovered by Baeyer in 1885. It was proposed as an antiseptic under the name Diiodoform, in 1893 by M. L. Maquenne and Taine. It was an alternative to iodoformNew 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). which has a strong and persistent odour that caused difficulties for physicians in private practices.Selections – DIIODOFORM in The International Dental Journal. (1895). USA: International Dental Publication Company.
Synthesis Tetraiodoethylene can be made by the iodination of calcium carbide:TETRA-IODO-ETHYLENE, The Pharmaceutical Era. (1897). USA, D. O. Haynes & Company.
Diiodoacetylene is a byproduct of the reaction which can later be iodinated to TIE.
The action of aqueous solution of potassium hydroxide and iodine on barium carbide in chloroform or benzene can also give TIE. 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.
See also 1,2-Diiodoethylene Triiodoethylene Tetrafluoroethylene Tetrachloroethylene Tetrabromoethylene
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