Yadav Abhishek Kumar, Kumar Navaneet, Ghule Vikas D, Dharavath Srinivas
Energetic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, Uttar Pradesh, India.
Department of Chemistry, National Institute of Technology Kurukshetra, Kurukshetra 136119, Haryana, India.
Org Lett. 2023 Dec 8;25(48):8606-8610. doi: 10.1021/acs.orglett.3c03277. Epub 2023 Nov 29.
In this work, we have synthesized 3,5-dihydrazinyl-4-nitro-1-pyrazole (), 9-nitro-1-pyrazolo[3,2-:5,1-']bis([1,2,4]triazole)-3,6-diamine (), and N-N-bonded ,'-{[4,4'-bi(1,2,4-triazole)]-3,3'-diyl}dinitramide () and its stable nitrogen-rich energetic salts in one and two steps in quantitative yields from commercially available inexpensive starting material 4,6-dichloro-5-nitropyrimidine (). Along with characterization via nuclear magnetic resonance, infrared, differential scanning calorimetry, and elemental analysis, the structures of and were confirmed by single-crystal X-ray diffraction. Interestingly, show excellent thermal stability (242, 221, 250, and 242 °C, respectively) compared to that of RDX (210 °C). Detonation velocities of , , , and range from 8992 to 9069 m s, which are better than that of RDX (8878 m s) and close to that of HMX (9221 m s). All of these compounds are insensitive to impact (10-35 J) and friction (360 N) sensitivity. These excellent energetic performances, stabilities, and synthetic feasibilities make compounds , , , and promising candidates as secondary explosives and potential replacements for the presently used benchmark explosives RDX and HMX.
在本工作中，我们以市售廉价起始原料4,6-二氯-5-硝基嘧啶为原料，通过一步法和两步法分别以定量产率合成了3,5-二肼基-4-硝基-1-吡唑（）、9-硝基-1-吡唑并[3,2 - :5,1 - ']双（[1,2,4]三唑）-3,6-二胺（）以及N - N键合的,'-{[4,4'-联（1,2,4-三唑）]-3,3'-二基}二硝酰胺（）及其稳定的富氮含能盐。通过核磁共振、红外光谱、差示扫描量热法和元素分析进行表征的同时，和的结构通过单晶X射线衍射得以确认。有趣的是，与RDX（210℃）相比，显示出优异的热稳定性（分别为242、221、250和242℃）。、、和的爆速范围为8992至9069 m/s，优于RDX（8878 m/s）且接近HMX（9221 m/s）。所有这些化合物对撞击（10 - 35 J）和摩擦（360 N）均不敏感。这些优异的含能性能、稳定性和合成可行性使得化合物、、、成为有潜力的二次炸药候选物以及当前使用的基准炸药RDX和HMX的潜在替代品。
