1,1-Diiodoethane

1,1-diiodoethane (bond and stick model).png 100 Ball and stick model correct ?? 1,1-diiodoethane(skeleton model).png 100 Skeletal model correct ?? 1,1-Diiodoethane1,1-Diiodoethane - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/68980 PubChem Compound Database National Center for Biotechnology Information 7 June 2017 USA Identification Ethylidene iodide 209-821-0 594-02-5 correct CAS CC(I)I 68980 62202 correct chemspider 1S/C2H4I2/c1-2(3)4/h2H,1H3 correct PubChem JNVXRQOSRUDXDY-UHFFFAOYSA-N 2 4 2 3.0±0.1 g/cm3CSID:8014297 http://www.chemspider.com/Chemical-Structure.8014297.html ChemSpider 7 June 2017 154.7±23.0 °C most organic solvents 06 07 WARNING 261 264 270 271 280 301+312 302+352 304+340 305+351+338 312 321 330 332+313 337+313 362 403+233 405 501 63.7±18.1 °C 1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH3CHI2. 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.Benneche T. Challenger S. Chemla F. Cordier C. Demchenko A. V. De Meo C. Diaper C. M. Fascione M. A. Ferreira F. Gunn S. J. Kouklovsky C. Kryezka B. Leach S. Leroy B. Lewkowaki J. Ley S. V. Merino P. Milroy L.-G. Myers R. M. Nelson A. Oshima K. Rowlands G. J. Roy B. Stalford S. A. Turnbull W. B. Angerer S. von Warriner S. L. White J. W. Yorimitsu H. Zawisza A. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Thieme New York 2007 29 106 978-1-58890-461-4 https://books.google.com/books?id=VSGGAwAAQBAJ&q=1%2C1-diiodoethane&pg=PA106 8 June 2017 thumb|center|500px|alt=The preparation of 1,1-diiodoethane from gem-dihaloalkanes.|The preparation of 1,1-diiodoethane from gem-dihaloalkanes 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.Taschner Michael J. e-EROS Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons 2001 10.1002/047084289X.rd239 1,1-Diiodoethane 978-0471936237 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. See also 1,2-Diiodoethylene 1,2-Difluoroethane 1,2-Diiodoethane 1,1-Dibromoethane 1,2-Difluoroethylene References External links PubChem Compound Summary for CID 68980 Chemistry of Ethylidene Moieties on Platinum Surfaces:  1,1-Diiodoethane on Pt(111) Category:Iodoalkanes Category:Haloethanes