Nitroacetonitrile as a versatile precursor in energetic materials synthesis

Nitroacetonitrile is the simplest alpha-nitronitrile; it possesses a single central carbon attached to two strong electronegative, electron-withdrawing groups allowing extensive chemistry through the active methylene center. Free nitroacetonitrile has purification and stability issues, however stable salts of nitroacetonitrile possess the same reactivity as the free acid and are much more stable. Nitroacetonitrile serves as a versatile synthetic precursor in the formation of heterocyclic and polyfunctional aliphatic products and can allow for straightforward conversion to amino, acyl, and other functional groups. A main advantage of using nitroacetonitrile in the formation of heterocyclic-based energetics is its ability to add vicinal amino and nitro moieties onto fused ring structures, a common structural motif in insensitive energetic materials. In this minireview we discuss the preparation of nitroacetonitrile and its stable salts, as well as discuss the range of energetic materials this versatile precursor has found use in.