1,3,5-Tris[(2H-tetrazol-5-yl)methyl]isocyanurate and Its Tricationic Salts as Thermostable and Insensitive Energetic Materials

Abstract

Various energetic salts (3a–f) were obtained from 1,3,5-tris­[(2H-tetrazol-5-yl)­methyl]­isocyanurate (3), while N2,N4,N6-tri­(1H-tetrazol-5-yl)-1,3,5-triazine-2,4,6-triamine (5) and N,N′-{6-[(1H-tetrazol-5-yl)­amino]-1,3,5-triazine-2,4-diyl}­bis­[N-(1H-tetrazol-5-yl)­nitramide] (6) were obtained from cyanuric chloride via a simple, efficient two-step synthetic route from inexpensive starting materials. Compounds 3a–f and 6 show excellent detonation properties (VOD = 7876–8832 m s–1, and DP = 20.73–30.0 GPa), a high nitrogen content (>62%), and high positive heats of formation (205.2–1888.9 kJ mol–1) with excellent thermostability and remarkable insensitivity.

Promising Thermally Stable Energetic Materials with the Combination of Pyrazole–1,3,4-Oxadiazole and Pyrazole–1,2,4-Triazole Backbones: Facile Synthesis and Energetic Performance

“…Further, compound 16 was reacted with 100% HNO 3 for 12 h at room temperature, forming (Z)-N-(5-(4nitro-1H-pyrazol-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)nitramide (18). 38 Compound 18 treated with various nitrogenrich bases in methanol to get energetic salts hydrazine (19), hydroxyl amine (20), and 7H- [1,2,4]triazolo [4,3-b][1,2,4]triazole-3,6,7-triamine (TATOT) (21) in quantitative yields. Compound 16 was diazotised using 37% HCl and KMnO 4 in water at 50 °C for 8 h, and the molecule (E)-1,2-bis(5-(4nitro-1H-pyrazol-3-yl)-1H-1,2,4-triazol-3-yl)diazene (22) was isolated in 52% yield.…”

“…Nitrogen-rich heterocycles such as pyrazole, oxadiazole, and triazole rich in C–N, O–N, and N–N bonds in their structures have drawn extensive attention for the design and preparation of nitrogen-rich materials owing to their inherently high energy content, density, high thermal stability, availability of sites for functional group substitution, and the ability to decompose into nitrogen gas. − The importance of these nitrogen-rich azole rings as energetic materials backbone has been well explored. Introducing azo-bridged and energy/oxygen-rich explosophoric groups (−N 3 , −NO 2 , −NHNO 2 , −ONO 2 , etc.)…”

Silver-Catalyzed Synthesis of 2-Cyano-5-pyrazolyl-2H-tetrazole: A Promising Precursor to Insensitive Energetic Compounds

“…The combination of pyrazole and tetrazole rings is beneficial to improving the detonation performance and safety of energetic compounds. However, traditional methods of constructing polycyclic energetic materials, such as nucleophilic substitution and functional transformation, have been widely reported, − which greatly limit the space for constructing new energetic skeletons. Therefore, exploring new synthetic methods for the synthesis of energetic materials has become one of the key factors for the breakthrough in the dilemma of energetic materials.…”

High-Energy and Insensitive Tetrazole-Substituted 2,5-Dinitroiminooctahydroimidazo[4,5-d]imidazole: Synthesis, Characterization, and Energetic Properties

“…Since Nobel’s successful improvement of the explosives manufacturing process, the development of energetic materials has received extensive attention in the military and civilian fields such as propellants, explosives, and so forth. − In the pursuit of high-performance energetic materials, although high energy has always been the primary consideration, there is a growing interest in the safety of energetic materials because of the increasing number of safety-related issues in practical applications. − However, to achieve a good balance between energy and safety remains a great challenge because high energy is mainly at the expense of molecular stability. − Therefore, a high-level energy material with a fine balance between energy and security is highly desirable.…”