Synthesis of [13C](C1–C6),[15N](N1,N2)-labeled 2,4-dinitroanisole (DNAN) and [13C](C3,C5),[15N](N6)-labeled 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO)

Abstract

ABSTRACT Manufacture and use of explosives in the past have led to environmental contamination by energetic materials. Today, there is an emphasis to better understand the environmental fate and transport of new and improved energetic materials before they can cause expensive or irreparable damage to an ecosystem. In order to conduct these environmental studies with the new insensitive energetic materials (IEM) 2,4-dinitroanisole (DNAN) and 5-nitro-1,2,4-triazol-3-one (NTO) their syntheses with isotopic labels was necessary. [13C](C1–C6),[15N](N1,N2)-labeled DNAN was synthesized in two-steps in 94% overall yield starting from chlorobenzene-13C6. [13C](C3,C5),[15N](N6)-labeled NTO was synthesized in three-steps in 28% overall yield starting from urea-13C.