Halogenated Esters
The use of ethyl iodoacetate was advocated at a time when the price of bromine seemed prohibitive. Because of the relative price of bromine and iodine under ordinary conditions, it is not likely that it would be commonly used. However, it is an efficient lachrymator and is more stable than the halogenated ketones, so that on a smaller scale it might be advisable to use it.
It is prepared by the reaction of sodium iodide upon an alcoholic solution of ethyl chloroacetate. It is a colorless oil, boiling at 178-180° C. (69° C. at 12 mm.) and having a density of about 1.8. It is very much less volatile than bromoacetone, having a vapor pressure of 0.54 mm. of mercury at 20° C. Ethyl iodoacetate is about one-third as toxic as bromoacetone, but has about the same lachrymatory value.