Alkylating Ionic Liquids (AILs) as synthetic reagents for practical and safe alkylators

One function that has yet to be introduced in to ionic liquids (ILs) is the ability to alkylate other molecules, where the IL can selectively transfer one of its alkyl groups to a nucleophile under mild conditions. Such alkylating ionic liquids (AILs) would combine the highly useful designer nature of ILs, such as tunable properties, solubility, and non-volatility, with the function of alkylation simultaneously. This approach would introduce a new platform for molecular design and scope with applications common to alkylators, such as synthesis, pharmaceuticals, cancer therapeutics (Mustargen and Cytoxan for example), gene expression and epigenetic modifications. This platform would also serve to conjugate these molecules to complex systems like biomolecules, polymers, materials, surfaces, particles, and others.  The benefits of AILs are numerous, including reduced exposure to otherwise toxic/carcinogenic alkylating agents, simplified transport, tunable reactivity, and their introduction in to polymers/materials using currently established methodologies.

Currently we have developed a library of AILs that are highly reactive once heated to their activation temperature, yet are otherwise non-volatile and non-reactive. The activation temperature is directly correlated to the IL structure and can be fine-tuned in a simple fashion. Unlike conventional alkylators, here these AILs undergo a chemical modification upon reaching their activation point, which then improves reactivity. In this fashion, we obtain both fast kinetics and improved safety. We are currently underway to investigate the use of these new reagents in biochemical systems and as novel alkylation reagents that are both cheap and safe.

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