1,1-Diiodoethane
Chemical compound
From Wikipedia, the free encyclopedia
1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH3CHI2.
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| Names | |||
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| Preferred IUPAC name
1,1-Diiodoethane[1] | |||
| Other names
Ethylidene iodide | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.008.930 | ||
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C2H4I2 | |||
| Molar mass | 281.863 g·molâ1 | ||
| Density | 3.0±0.1 g/cm3[2] | ||
| Boiling point | 154.7±23.0 °C | ||
| Solubility | most organic solvents | ||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |||
| Flash point | 63.7±18.1 °C | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
1,1-Diiodoethane can be synthesized from gem-dihaloalkanes. The starting material is 1,1-dichloroethane, and iodoethane is a source of iodine. In the presence of aluminium trichloride, 1,1-dichloroethane will converted to 1,1-diiodoethane.[3]
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To be specific, mix 0.4 mol (~39.6 g) of 1,1-dichloroethane with 1.2 mol (~187 g) of ethyl iodide, and ~2.0 g of aluminium chloride. Heat for three hours using steam bath. Then, wash the mixture with H2O and NaHSO3 respectively, and dry with MgSO4. By boiling at 76-76 °C and 25 mmHg, about 67.3 g of product will be received when distilled.[4]
The alternative method, which does not require 1,1-dichloroethane, is the reaction of iodine, triethylamine and hydrazone of acetaldehyde. Using 1 mol of acetaldehyde, about 95 g, which is 34% from acetaldehyde, of 1,1-diiodoethane formed.[4]