Tetraiodoethylene

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Tetraiodoethylene
Tetraiodoethylene.png
C2I4 3D.png
Names
IUPAC name
Tetraiodoethene
Other names
  • Periodoethylene
  • Periodoethene
  • Diiodoform
  • Ethylene tetraiodide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.434 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-176-2
PubChem CID
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
Appearanceyellow crystalline solid
Odor Odourless [1]
Density 2.98 g/cm3
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] sparingly soluble in ether [3]
Hazards
GHS labelling: [4]
GHS-pictogram-exclam.svg
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
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetraiodoethylene, TIE or diiodoform, is an organoiodine compound with the chemical formula C2I4. Its structure is I2C=CI2. 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. [5] [6] It is the periodinated analogue of ethylene. It is a decomposition product of carbon tetraiodide and diiodoacetylene. [7]

Contents

Tetraiodoethylene reacts with ethylamine to give ethylamine di-tetraiodoethylene, CH3CH2NH2·(C2I4)2, and ethylamine tetraiodoethylene, CH3CH2NH2·C2I4. [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. [7] 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]

CaC2 + 3 I2 → 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

References

  1. 1 2 3 TETRA-IODO-ETHYLENE, The Pharmaceutical Era. (1897). USA, D. O. Haynes & Company.
  2. 1 2 3 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. 1 2 Diiodoform in Notes on New Remedies. (1893). USA: Lehn & Fink.
  4. ↑ "Tetraiodoethylene". pubchem.ncbi.nlm.nih.gov.
  5. ↑ The Code of Federal Regulations of the United States of America (1984). U.S. Government Printing Office.
  6. ↑ Iodine and Plant Life: Annotated Bibliography, 1813-1949. With Review of the Literature. (1950). UK: Chilean Iodine Educational Bureau. page 22
  7. 1 2 Peculiar Decomposition of Diiodoacetylene, Victor Meyel and Wilhelm Pemsel (1896)
  8. ↑ Action of Tetraiodoethylene on Organic Bases, Chemical Abstracts. (1912). American Chemical Society.
  9. ↑ Journal of the Chemical Society. (1948). page 2188
  10. 1 2 3 4 5 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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