Potentially harmful disinfection byproducts, formed through the reaction of disinfectants with natural water constituents, are a long-standing challenge of water disinfection. Recently, chloronitramide was revealed as the long-standing unidentified product of chloramine decay [1]. Chloronitramide as a disinfection byproduct, is unique, in that it is formed in the decomposition of chloramines and does not, to our knowledge, require additional precursors, unlike regulated disinfection byproduct classes, including trihalomethanes, haloacetic acids, and nitrosamines. Although the structure of chloronitramide was finally elucidated last year, it remains unknown if brominated and iodated analogues form in drinking water systems. To this end, work is underway to synthesize pure standards of chloronitramide, bromonitramide, and iodonitramide. We have developed successful synthetic routes albeit with modest yields to produce chloronitramide and bromonitramide. Optimized synthetic pathways will be discussed along with challenges in the analytical methodologies needed for these disinfection byproducts. Drinking water samples from chloraminated water systems that have source water with elevated bromide and iodide levels will be obtained to determine whether these bromonitramide and iodonitramide are formed in real systems. Overall, these results will inform risk assessment by providing occurrence data for halogenated nitramines, a novel class of disinfection byproducts.

[1] J.L. Fairey, J.R. Laszakovits, H.T. Pham, T.D. Do, S.D. Hodges, K. McNeill, D.G. Wahman, Science, 2024, 386, 882-887