From Nitro- to Heterocycle-Functionalized 1,2,4-Triazol-3-one Derivatives: Achieving High-Performance Insensitive Energetic Compounds

Abstract

5-Nitro-1,2,4-triazol-3-one, a nitro-functionalized 1,2,4-triazol-3-one (TO) derivative, shows excellent energetic properties and promising application potential. However, the use of the TO skeleton as an energetic material is still largely underexplored both theoretically and practically. We report here a mild and efficient method for obtaining the TO skeleton via a reaction of aminocarbohydrazide with BrCN. Two energetic compounds (2 and 5) were synthesized and fully characterized by 15 N nuclear magnetic resonance, two-dimensional 1 H− 15 N heteronuclear multiple-bond correlation, and single-crystal X-ray diffraction. The reaction mechanism was also studied with the aid of quantum calculations. Compound 2 shows promising properties as a high-performance insensitive energetic material.

Increasing the Energy Limit of Single Triazole–Tetrazole: HNANTT Modified with Its Energetic Coordination Polymers, Co-Crystals, and Energetic Salts

“…The oxygen balance (OB), based on CO (%), is a parameter used to describe the balance between the oxygen required and released during the combustion of energetic materials, which reflects the thermodynamic properties such as gas yield, flame temperature, and detonation velocity. ,, As shown in Table , the oxygen balance of NANTT and NANTT-ECPs were all 0.00%, same as the RDX and HMX, which indicated that NANTT and NANTT-ECPs can undergo full combustion during the explosion process to generate CO, H 2 O, and N 2 and resulting in a relatively complete release of heat at the same time.…”

Synthesis and Properties of 1,2,4-Triazol-3-one-Based Energetic Compounds

“… a Thermal decomposition temperature (heating rate: 5 °C min –1 ). b Measured density at 298 K. c Calculated enthalpy of formation in the solid state. d Detonation velocity. e Detonation pressure. f Impact sensitivity. g Friction sensitivity. h ref . i ref . j ref . …”

“…In 2022, Tang’s group reported two TO derivatives: 4-((1 H -tetrazol-5-yl) amino)-5-amino-2,4-dihydro-3 H -1,2,4-triazol-3-one ( III ) and 5-amino-4-(4-amino-1,2,5-oxadiazol-3-yl)-2,4-dihydro-3 H -1,2,4-triazol-3-one ( IV ). Compound III has a high detonation performance ( D v = 9034 m s –1 ) and a low sensitivity (IS = 18 J) and could be used as a high-performance insensitive energetic material (Figure b). , All four TO derivatives have good detonation performances, high densities, and low mechanical sensitivities. However, none of them can be used as heat-resistant energetic materials because of their low decomposition temperatures ( T d = 127; 164; 228; 244 °C).…”

“…However, not all these derivatives are suitable as energetic materials, such as 4-amino-2,4-dihydro-3H-1,2,4-triazol-3-one (ATO) and 4,4'-(diazene-1,2-diyl) bis ) and a low sensitivity (IS = 18 J) and could be used as a high-performance insensitive energetic material (Figure 1b). 24,25 All four TO derivatives have good detonation performances, high densities, and low mechanical sensitivities. However, none of them can be used as heat-resistant energetic materials because of their low decomposition temperatures (T d = 127; 164; 228; 244 °C).…”

Construction of High-Performance Energetic MOFs: C4N8O42– and C3N4O42– with Their Derivatives, Compared with Their Energetic Salts

“…Currently, the ever-growing demand for new energetic materials (EMs) with significant amounts of energy and superior stability has become a high priority in explosives, propellants, and pyrotechnics in society. − An increasing number of researchers have attempted to handle the inherent contradiction of EMs and energy with stability to improve their comprehensive performances. − Energetic salts, particularly energetic metal–organic frameworks ( E -MOFs), provide a new strategy. − …”