1,1-diiodoethane
1,1-diiodoethane Basic information
- Product Name:
- 1,1-diiodoethane
- Synonyms:
-
- 1,1-diiodoethane
- Ethylidene diiodide
- unsym-Diiodoethanee
- 1,1-Diiodoethane >=98.0% (GC)
- Ethane, 1,1-diiodo- (7CI,8CI,9CI)
- CAS:
- 594-02-5
- MF:
- C2H4I2
- MW:
- 281.86
- EINECS:
- 209-821-0
- Mol File:
- 594-02-5.mol
1,1-diiodoethane Chemical Properties
- 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
Safety Information
- Hazard Codes
- Xn
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26
- WGK Germany
- 3
1,1-diiodoethane Usage And Synthesis
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.