Synthesis and Characterization of N5-(2-Fluoro-2,2-dinitroethyl)-N1-methyl-1H-tetrazole-5-amine and its Nitramide Based on Functionalized Amino Group in 5-Amino-1H-tetrazole

N-5-(2-fluoro-2,2-dinitroethyl)-N-1-methyl-1H-tetrazole-5-amine and its nitramide were designed and synthesized by a strategy based on functionalized amino group in 5-amino-1H-tetrazole. Their structures were fully determined by H-1, (CNMR)-C-13, infrared spectrum as well as elementary analysis. Single-crystal X-ray diffraction was employed for characterizing their crystal structures. Comparing with its nitramide N-5-(2-fluoro-2,2-dinitroethyl)-N-1-methyl-1H-tetrazol-5-yl)-nitramide (T-m: 76 C-o, T-d: 135 C-o, T-p: 163 C-o), N-5-(2-fluoro-2,2-dinitroethyl)-N-1-methyl-1H-tetrazole-5-amine exhibits better thermal stability (T-m: 167 C-o, T-d: 191 C-o, T-p: 205 C-o), which is superior to those of N-3,N-4-bis(2-fluoro-2,2'-dinitroethyl)-1,2,5-oxadiazole-3,4-diamine (LLM-208) (T-m: 149 C-o, T-p: 188 C-o). They both present insensitivity towards impact but slightly sensitive to friction. It is worth noting that N-5-(2-fluoro-2,2-dinitroethyl)-N-1-methyl-1H-tetrazol-5-yl)-nitramide shows its detonation performance approaching those of RDX. The above-mentioned energetic performance show that they are insensitive and worth further potential applications as oxidizers, melt-cast explosives, energetic plasticizers, or high-performance ligands for constructing energetic coordination polymers.