Compared with the well-established 2,2,2-trinitroethyl group in the chemistry of energetic materials, the 3,3,3-trinitropropyl group is less investigated regarding its chemical and energetic properties. Thus, investigations on the syntheses of several compounds containing the 3,3,3-trinitropropyl group were performed and their properties compared with the 2,2,2-trinitroethyl group. All materials were thoroughly characterized, including single-crystal X-ray diffraction studies. The thermal stabilities were examined using differential thermal analysis (DSC) and the sensitivities towards impact, friction, and electrostatic discharge were tested using a drop hammer, a friction tester, and an electrical discharge device. The energies of formation were calculated and several detonation parameters such as the velocity of detonation and the propulsion performance were estimated with the program package EXPLO5.