1-Chloro-2-iodoethane is used as a mild electrophile for iodination of metallated species, as in the conversion of an ortho-lithiated benzyl ether to the corresponding ortho-iodide. It reacts with 5-hydroxy-[1,4]naphthoquinone, and obtain the 5-(2-chloro-ethoxy)-[1,4]naphthoquinone.
The Preparative Methods of 1-chloro-2-iodoethane: prepared in 76% yield by bubbling Ethylene gas into a CH2Cl2 solution of freshly redistilled Iodine Monochloride maintained at 30 °C by ice-cooling until the temperature begins to fall. Other methods of preparation include reaction of ethylene, Copper(II) Chloride, and Iodine at 75-85 °C in a pressure reactor; reaction of excess 1,2-dichloroethane with Sodium Iodide in acetone or with Aluminum Iodide in CS2; and by reaction of 2-iodoethanol with Thionyl Chloride.
1-chloro-2-iodoethane that is exposed to light and air develops a slight rose-colored tint due to the formation of I2. It is usually suitable for use unless the color is very pronounced. The compound is purified by washing with aq thiosulfate and redistillation at reduced pressure.
1-chloro-2-iodoethane is a dialkylating agent and should be used only in an effective fume hood. Avoid inhalation of the vapour and contact of the liquid with the skin. The compound is light-sensitive and should be stored refrigerated in the dark.
