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Names | |||
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Preferred IUPAC name
1,1-Diiodoethane
[1] | |||
Other names
Ethylidene iodide
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Identifiers | |||
3D model (
JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.008.930 | ||
EC Number |
| ||
PubChem
CID
|
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CompTox Dashboard (
EPA)
|
|||
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Properties | |||
C2H4I2 | |||
Molar mass | 281.863 g·mol−1 | ||
Density | 3.0±0.1 g/cm3 [2] | ||
Boiling point | 154.7±23.0 °C | ||
Solubility | most organic solvents | ||
Hazards | |||
GHS labelling: | |||
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).
|
1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH3CHI2.
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]
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]
1,1-Diiodoethane is commonly used as a reactant in reaction such as SN2. The following are some examples of SN2 reaction using 1,1-diiodoethane as a reactant. [5]
Moreover, is can also be used as a reactant in enolate substitution reaction as the following examples. [5]
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
1,1-Diiodoethane
[1] | |||
Other names
Ethylidene iodide
| |||
Identifiers | |||
3D model (
JSmol)
|
|||
ChemSpider | |||
ECHA InfoCard | 100.008.930 | ||
EC Number |
| ||
PubChem
CID
|
|||
CompTox Dashboard (
EPA)
|
|||
| |||
Properties | |||
C2H4I2 | |||
Molar mass | 281.863 g·mol−1 | ||
Density | 3.0±0.1 g/cm3 [2] | ||
Boiling point | 154.7±23.0 °C | ||
Solubility | most organic solvents | ||
Hazards | |||
GHS labelling: | |||
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).
|
1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH3CHI2.
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]
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]
1,1-Diiodoethane is commonly used as a reactant in reaction such as SN2. The following are some examples of SN2 reaction using 1,1-diiodoethane as a reactant. [5]
Moreover, is can also be used as a reactant in enolate substitution reaction as the following examples. [5]