| Identification | Back Directory | [Name]
1,1-diiodoethane | [CAS]
594-02-5 | [Synonyms]
1,1-diiodoethane
Ethylidene diiodide
unsym-Diiodoethanee
1,1-Diiodoethane >=98.0% (GC)
Ethane, 1,1-diiodo- (7CI,8CI,9CI) | [EINECS(EC#)]
209-821-0 | [Molecular Formula]
C2H4I2 | [MDL Number]
MFCD00015747 | [MOL File]
594-02-5.mol | [Molecular Weight]
281.86 |
| Chemical Properties | Back Directory | [Melting point ]
63.01°C (estimate) | [Boiling point ]
223.38°C (estimate) | [density ]
2.7600 | [refractive index ]
1.6500 | [storage temp. ]
-20°C | [form ]
liquid | [BRN ]
1730848 |
| Hazard Information | Back Directory | [Uses]
1,1-diiodoethane is a reagent for methylcyclopropanation of alkenes and ethylidenation of carbonyl compounds.
| [Synthesis Reference(s)]
Journal of the American Chemical Society, 73, p. 4476, 1951 DOI: 10.1021/ja01153a524 | [Synthesis]
The Preparative Methods of 1,1-diiodoethane: mix 39.6 g (0.40 mol) of 1,1-dichloroethane, 187 g (1.2 mol) of ethyl iodide, and 2.0 g of Aluminum Chloride and heat on a steam bath for 3 h; wash the mixture with H2O and then NaHSO3, and dry over MgSO4; distillation provides 67.3 g (60%) of the product 1,1-diiodoethane boiling at 75-76 °C/25 mmHg. An alternative procedure utilizes the reaction of Iodine, Triethylamine, and the hydrazone of Acetaldehyde: from 1 mol of acetaldehyde, 95 g (34% from acetaldehyde) of 1,1-diiodoethane can be isolated; this procedure is a little more involved but provides a viable alternative if 1,1-dichloroethane is not available.
| [Precautions]
Corrosive and irritant; emits toxic fumes if heated to decomposition or mes in contact with acids. Use in a fume hood; store over copper powder and protect from light.
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