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| | 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 | | Product Categories: | | | 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 | | InChI | 1S/C2H4I2/c1-2(3)4/h2H,1H3 | | InChIKey | JNVXRQOSRUDXDY-UHFFFAOYSA-N | | SMILES | CC(I)I |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 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.
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| | 1,1-diiodoethane Preparation Products And Raw materials |
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