ALKYLATION OF 2,4,5-TRIIODOIMIDAZOLE MOLECULES

Abstract

Alkylated 2,4,5,-triiodoimidazole molecules could be of interesting in a variety of situations, including pharmaceuticals and complex molecule synthesis. The most obvious route to such compounds is the alkylation of 2,4,5-triiodoimidazoles with alkyl halides. Interestingly, little has been reported in this area. In conjunction with our interest in highly iodinated compounds, we undertook a study of this alkylation. Reactions of various types of alkyl halides were studied. In most cases, reactions were performed at room temperature in dimethylformamide (DMF) with potassium carbonate, although some less reactive alkyl halides required heating. The future goal is to use these alkylated triiodoimidazoles in energetic and biological applications. In an attempt to synthesize energetic binders to replace current isocyanate-based binders, my target begins with 2,4,5-triiodoimidazole which is alkylated on one of the nitrogens using allyl bromide. The tethered alkene can be later used to crosslink the final polymer, replacing the isocyanate crosslinker. These energetic binders make transporting volatile materials safer. This stabilization is provided by a surrounding structure of the binder molecule, that upon crosslinking will combine to become larger units. The resulting matrix makes the explosive more thermodynamically stable by being able to absorb more shock.