N‐Alkylation of 4‐Hydroxy‐3,5‐Dinitropyrazole: A Facile Route for the Synthesis of Insensitive Energetic Materials

Propellants Explosives Pyrotechnics, Год журнала: 2025, Номер unknown

Опубликована: Фев. 4, 2025

ABSTRACT Behind the synthesis of any new high‐energy density material is objective to achieve equilibrium between energy and stability, which becomes laborious because their adversarial nature. Nitropyrazoles, with viable syntheses easy modifiability, have been adopted typically as backbones this goal. However, acidic nature pyrazole N H in nitropyrazoles limits usefulness despite exhibiting appealing characteristics. 4‐Hydroxy‐3,5‐dinitropyrazole (HODNP) an interesting skeleton presence hydroxy functionality two nitro groups, not only provides additional oxygen content for better output but also possesses quality strong hydrogen bonding interactions tuning properties via salt formation. N‐alkylation most straightforward technique protection unwanted proton, addition making them more physically stable. In work, we synthesized ‐methylated , N’ ‐ethylene‐bridged derivatives ( 2 7 ) HODNP. Mono dicationic salts 3 ‐ 6 8 11 were boost performance further. N‐methylated neutral compound its ammonium confirmed through 15 NMR analysis, was single‐crystal analysis. All compounds showed excellent physical stability (IS >40 J, FS > 360 N), good thermal (T d 180°C). The detonation characteristics found be similar ones 1,3,5‐triamino‐2,4,6‐trinitrobenzene (D v = 7704–8172 m/s, p 22.4–27.3 GPa).

Язык: Английский

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Understanding how Molecular Skeletal Isomerism Affects the Stability of Energetic Fused-ring Molecules: a Comparative Study of ICM-103 and NAPTO

Energetic Materials Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Март 1, 2025

Язык: Английский

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Promising Energetic Asymmetric Bistetrazoles Synthesized via Sequential Cycloaddition Reactions

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Herein, we report the successful synthesis of a series asymmetric bistetrazole-based energetic compounds (4, 8, 4a-c, and 5a-c) starting from 2-(5-amino-4-nitro-1H-pyrazol-3-yl)-2H-5-cyanotetrazol (3), which was obtained via reaction 3,5-diamino-4-nitropyrazole hydrochloride with diazoacetonitrile using [3 + 2] cycloaddition strategy. All newly synthesized displayed superior detonation performances, particularly 2'-(5-amino-4-nitro-1H-pyrazol-4-yl)-2H,2'H-5,5'-bistetrazole (4), exhibited exceptional overall performances. These findings underscore potential bistetrazole derivatives as promising candidates for development advanced materials.

Язык: Английский

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Integration of 1,2,3-Triazine N-Oxide and 2,4,6-Trinitroaniline Moieties for the Design of Heat-Resistant Energetic Compounds

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Heat-resistant energetic compounds are of great importance in the field material chemistry. Here, we report a practical synthesis series fused-ring via combination 1,2,3-triazine N-oxide and 2,4,6-trinitroaniline moieties. Starting from known compound 4,6-diamino-2-chloropyrimidine-5-carbonitrile (1), nucleophilic substitution followed by one-step nitration introduced three nitro groups onto benzene ring moiety, simultaneously. The resulting 4-7 exhibited high decomposition temperature (Td > 250 °C) as well relatively good detonation properties low sensitivities.

Язык: Английский

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4,4′-Dimethyl-1,1′-bi(1,2,3-triazole): exploring new insensitive energy source materials

New Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

One step oxidation in a long nitrogen chain compound with good detonation properties.

Язык: Английский

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Bistetrazoles Featuring Ultra Thermal Stability

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

As the global demand for mining resources continues to rise and as advances in aerospace exploration accelerate, need high-performance energetic materials capable of withstanding extreme conditions has become increasingly critical. This study focuses on rational design synthesis a series molecules incorporating bistetrazole chiral diol functional groups. The inclusion units enhances performance stability these compounds, while groups contribute their structural integrity.

Язык: Английский

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1,3,4-Oxadiazole-Bridged 3,5-Dinitropyrazoles: Powerful Alliance toward High Performance and High Thermal Stability

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 3, 2025

The ever-increasing demand for heat-resistant energetic materials in deep mining and space exploration has led to significant interest developing new with exceptional thermal stability detonation performance. In this work, a novel compound, 2,5-bis(3,5-dinitro-1H-pyrazol-4-yl)-1,3,4-oxadiazole (3), was achieved through simple straightforward method where two 3,5-dinitropyrazole moieties are linked 1,3,4-oxadiazole ring. Compound 3, symmetrical conjugated molecule, demonstrates superior (Tdec = 325 °C), good performance (Dv 8464 m s-1), improved physical (IS 7.5 J) compared the industrially used explosive, HNS. properties of 3 were further optimized by forming salts, 4 5. An attempted reaction synthesize zwitterionic compound 7, having 3,5-diamino-1,2,4-triazole ring connected via C-C bond, resulted another 6. Energetic salts 291 °C) 5 275 as well 6 286 demonstrated excellent decomposition temperatures stability. dihydroxylammonium salt (5) 8507 s-1, P 31.25 GPa) exhibited best properties, approaching RDX. remarkable overall compounds 3-5 makes them suitable candidates high-performance, explosives.

Язык: Английский

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Towards advanced N-rich energetic explosives: based on tetrazole and triazole groups with large conjugated systems and extensive hydrogen bonds

Journal of Materials Chemistry A, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The N3-3 molecule has achieved superior overall performance among N-rich energetic materials ( T d = 302 °C and D v 9341 m s −1 ), which significantly surpasses that of HMX.

Язык: Английский

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Molecular modification of energetic fused 1,2,3-triazine 2-oxides: an effective approach to achieve enhanced thermal stability and detonation performance.

Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 141126 - 141126

Опубликована: Дек. 1, 2024

Язык: Английский

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