1,3-Dichloro-2-nitro-2-azapropane is an excellent precursor to dense energetic functionalized dipyrazolyl-N-nitromethanamines. This new family of energetic compounds was fully characterized by using 1H, 13C, and 15N NMR and IR spectroscopy, differential scanning calorimetry, elemental analysis, and impact sensitivity tests. Additionally, single-crystal X-ray structuring was done for 3 and 5⋅CH3CN, which gave insight into structural characteristics. The experimentally determined densities of 2–9 fall between 1.69 and 1.90 g cm−3. Heats of formation and detonation properties were calculated by using Gaussian 03 and EXPLO5 programs, respectively. The influence of different energetic moieties on the structural and energetic properties was established theoretically.