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Names | |||
---|---|---|---|
IUPAC name
tetraiodoethene
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Other names
Periodoethylene, Periodoethene, Diiodoform, Ethylene tetraiodide
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Identifiers | |||
3D model (
JSmol)
|
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ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.434 | ||
EC Number |
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PubChem
CID
|
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UNII | |||
CompTox Dashboard (
EPA)
|
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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] | |||
![]() | |||
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 (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 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]
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]
Tetraiodoethylene can be made by the iodination of calcium carbide: [1]
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]
| |||
Names | |||
---|---|---|---|
IUPAC name
tetraiodoethene
| |||
Other names
Periodoethylene, Periodoethene, Diiodoform, Ethylene tetraiodide
| |||
Identifiers | |||
3D model (
JSmol)
|
|||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.434 | ||
EC Number |
| ||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
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] | |||
![]() | |||
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 (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 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]
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]
Tetraiodoethylene can be made by the iodination of calcium carbide: [1]
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]