Combining Performance with Thermal Stability: Synthesis and Characterization of 5‐(3,5‐Dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its Energetic Derivatives

Abstract

In this study, we present the synthesis of 5‐(3,5‐dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole and its energetic derivatives starting from 4‐amino‐3,5‐dinitropyrazole, which was diazotized and cyanide substituted. A subsequent cycloaddition reaction with sodium azide led to 5‐(3,5‐dinitro‐1H‐pyrazol‐4‐yl)‐1H‐tetrazole (3). Several alkaline metal and nitrogen‐rich salts were prepared and characterized by low‐temperature X‐ray diffraction. Additionally, all compounds were analyzed by vibrational spectroscopy (IR), 1H, 13C and 14N NMR spectroscopy, elemental analysis and differential thermal analysis (DTA). Additionally, the heats of formation for selected compounds were calculated using the atomization method based on CBS‐4M enthalpies as well as important detonation parameters by using the EXPLO5 code (V6.05). Furthermore, the sensitivities of 3 and all synthesized salts toward friction, impact and electrostatic discharge according to BAM (Bundesamt für Materialforschung) were determined and compared to RDX.

4H-[1,2,3]Triazolo[4,5-c][1,2,5]oxadiazole 5-oxide and Its Salts: Promising Multipurpose Energetic Materials

“…Generally, such systems show good thermochemical stability and high heats of formation . One of the modern strategies to obtain energetic materials with high detonation performance involves combining a number of heterocyclic rings (e.g., furazans, furoxans, triazoles, tetrazoles, tetrazines, N-oxides of heterocycles), which would give a combination of the advantages of each of the units. − …”

Energetic multifunctionalized nitro/nitramino isomeric pyrazole–tetrazole hybrids: enhancing density and detonation properties through hydrogen bonding and π–π interactions

“…26 Benz reported the rst example of a fully nitro-functionalized pyrazole-tetrazole hybrid, 5-(3,5-dinitro-1H-pyrazol-4-yl)-1H-tetrazole (H 2 DNP-4T), and its energetic derivatives. 27 However, compound H 2 DNP-4T exhibits low detonation performance (D v : 8062 m s −1 ; P: 26 GPa) because of its low density of 1.669 g cm −3 , which results from the non-coplanarity of both rings (Scheme 2). Achieving a density > 1.80 g cm −3 is imperative for the fabrication of advanced EMs, as it is directly contributing to the high detonation performance.…”

Polynitro-Functionalized Azopyrazole with High Performance and Low Sensitivity as Novel Energetic Materials

“…4c, each coordinated K(I) ion is bonded by five O atoms and four N atoms from three TNAP 2anion ligands, with O−K and N−K bond distances in the length range of 2.686(1)−2.847(1) Å, which are in the normal range compared with previously reported K(I) metal−organic frameworks (MOFs). 38,39 The TNAP 2ligands in the single-crystal structure of K 2 TNAP display a μ 8 -mode, while its four nitro groups and −NN− of pyrazole display the uniform chelating mode (Figure 4d). In the two-dimensional structure (ac-plane), the bridged nitro groups connect the K centers into chains of K−O−N−O−K with K...K = 6.976 Å, whereas the K ions are bridged (K...K = 4.995 Å) by azo groups (Figure 4d).…”