4-hydroxy-3,5-dinitropyrazole | 1092799-14-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-hydroxy-3,5-dinitropyrazole
• 英文别名: 4-Hydroxy-3,5-dinitro-1H-pyrazole；3,5-dinitro-1H-pyrazol-4-ol
• CAS: 1092799-14-8
• 化学式: C₃H₂N₄O₅
• 分子量: 174.073
• InChiKey: MHHCWYNIYJZBIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3,5-dinitropyrazole 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以86%的产率得到lithium 3,5-dinitropyrazolate
  参考文献：
  名称：

  硝基吡唑锂作为潜在的红色烟火着色剂

  摘要：

  评估了聚硝基吡唑的锂盐作为红色烟火着色剂的适用性。虽然 3,4-二硝基吡唑锂和 3,4,5-三硝基吡唑锂具有吸湿性，但 3,5-二硝基吡唑锂和 4-氧代-3,5-二硝基吡唑锂对点火刺激有反应。4-氨基-3,5-二硝基吡唑类似物是该行中最不敏感的化合物，它被应用于产生主波长为 599 nm 的橙红色光的耀斑配方中。

  DOI：

  10.1002/ejic.202101048
• 作为产物：
  描述：

  3,4,5-trinitropyrazole 在 sodium hydroxide 、 水 作用下， 反应 3.0h， 生成 4-hydroxy-3,5-dinitropyrazole
  参考文献：
  名称：

  WO2008/152525

  摘要：

  公开号：

文献信息

• Selective Preparation of 3,4,5-Trinitro-1<i>H-</i>Pyrazole: A Stable All-Carbon-Nitrated Arene
  作者：Grégoire Hervé、Christian Roussel、Hervé Graindorge

  DOI：10.1002/anie.201000764

  日期：2010.4.19

  Lowering the boom: 3,4,5‐trinitro‐1H‐pyrazole (TNP, see picture) has been prepared by the unexpected nitration of 3,5‐dinitropyrazole with a super‐electrophile generated from 20–30 % sulfuric oleum mixed with nitric acid. The remarkable stability of TNP results from the preservation of the ring geometry and the specific conformation of the nitro group at C4 which confers low acidity on the material

  降低起重臂：3,4,5-三硝基-1 H-吡唑（TNP，参见图片）是通过将20,30％硫酸发烟硫酸与硝酸。TNP的显着稳定性来自保留环的几何形状和C4处硝基的特定构象，从而赋予了该材料低酸度。
• Construction of Layered High-Energy Materials via Directional Hydrogen Bonding
  作者：Yongan Feng、Jie Wang、Zhimin Li

  DOI：10.1021/acs.cgd.1c00537

  日期：2021.8.4

  Energetic substances with layered crystal packing have been identified as the most promising next-generation high-energy materials (HEMs) due to their excellent insensitivity. The challenge, however, is how to design layered HEMs. In this study, a novel strategy called “acceptor–donor separation” was proposed to control the layer-by-layer stacking of energetic molecules through directional hydrogen boding: that is, a hydrogen bond donor and acceptor are located in different energetic segments and at least one of them has a conjugated planar structure, which will enable the energetic fragments to be infinitely extended in a two-dimensional plane to form a target layered structure. The experimental results showed that three exemplary substances designed by using this strategy possess the expected layered structures, which have been confirmed by single-crystal X-ray diffraction, demonstrating the robustness of this strategy. Moreover, the three as-synthesized HEMs all exhibit excellent insensitivity (impact sensitivity IS > 40 J; friction sensitivity FS > 360 N), affording safety far beyond those of the most powerful HEMs in use today. Especially, the hydroxylammonium energetic salts possess good detonation performance (detonation velocity D = 8924 m s–1; detonation pressure P = 36.9 GPa) comparable to that of 1,3,5-trinitro-1,3,5-triazine (RDX), one of the most powerful high explosives in use today.

  具有层状晶体结构的高能物质因其卓越的不敏感性而被认为是最有前途的下一代高能材料（HEMs）。然而，如何设计层状高能材料是一项挑战。本研究提出了一种名为 "受体-供体分离 "的新策略，通过定向氢键来控制高能分子的逐层堆积：即氢键供体和受体位于不同的高能片段，且其中至少有一个具有共轭平面结构，从而使高能片段在二维平面上无限延伸，形成目标层状结构。实验结果表明，利用这一策略设计的三种示例物质具有预期的层状结构，并通过单晶 X 射线衍射得到了证实，证明了这一策略的稳健性。此外，这三种合成的 HEM 都具有出色的不敏感性（冲击敏感性 IS > 40 J；摩擦敏感性 FS > 360 N），其安全性远远超过了目前使用的最强 HEM。特别是羟基铵高能盐具有良好的起爆性能（起爆速度 D = 8924 m s-1；起爆压力 P = 36.9 GPa），可与目前使用的威力最大的烈性炸药之一 1,3,5-三硝基-1,3,5-三嗪（RDX）相媲美。
• Multidimensional Energetic Coordination Polymers as Flame Colorants: Intriguing Architecture and Excellent Performance
  作者：Wen-Shuai Dong、Xiaojun Wang、Chao Zhang、Lu Zhang、Yong Hu、Wenli Cao、Xiaowei Wu、Tingwei Wang、Jian-Guo Zhang

  DOI：10.1021/acs.cgd.2c00539

  日期：2022.9.7

  was combined in a specific and characteristic manner. All the prepared ECPs show excellent thermal stability, and the decomposition temperatures are higher than 347.0 °C (ECP-9) and 418.0 °C (ECP-1), due to the numerous coordination bonds and the network structure of the complex. The sensitivities toward impact and friction were tested using standard methods, and most of ECPs (ECP-1, ECP-2, and ECP-6

  在寻求“绿色”高能配位聚合物 (ECP) 的同时，制备了一种灵活的多功能 4-羟基-3,5-二硝基吡唑 (DNPO) 配体。成功制备了DNPO的一系列碱金属和碱土金属ECPs，并采用元素分析、红外光谱、差示扫描量热法和热重分析对其进行了综合表征。所有 ECP 均通过单晶 X 射线衍射进行表征。它们具有高晶体密度，范围从 1.743 ( ECP-6 ) 到 3.399 g cm –3 ( ECP-5）。此外，还发现了各种形状的零维（0D）、一维（1D）、二维（2D）和三维（3D）超分子结构来制备ECP，并且每种金属结合在一个具体而有特色的方式。所制备的 ECPs 均表现出优异的热稳定性，由于配合物众多的配位键和网络结构，其分解温度均高于 347.0 ℃（ECP-9）和 418.0 ℃ （ECP-1 ）。使用标准方法测试了对冲击和摩擦的敏感性，并且大多数 ECP（ECP-1、ECP-2和ECP-6到ECP-9)
• Energetic bimetallic complexes as catalysts affect the thermal decomposition of ammonium perchlorate
  作者：Wen-Shuai Dong、Wen-Li Cao、Qamar-un-Nisa Tariq、Xiao-Wei Wu、Yong Hu、Chao Zhang、Jian-Guo Zhang

  DOI：10.1039/d2dt00593j

  日期：——

  analyses. The results showed that BMEP-1 and BMEP-2 exhibited excellent catalytic performance in the thermal decomposition of ammonium perchlorate. Notably, there was only a single exothermic peak at 302.6 °C and 318.6 °C, and the activation energy values of ammonium perchlorate decreased to 123.88 kJ mol−1 and 128.43 kJ mol−1, respectively. TGA-FTIR results showed that BMEP-1 and BMEP-2, as effective components

  4-羟基-3,5-二硝基吡唑的两种双金属配合物，[K 2 Mn(DNPO) 2 (H 2 O) 4 ] n ·2H 2 O ( BMEP-1 ) 和 [K 2 Zn(DNPO) 2 (H 2 O) 6 ] n ( BMEP-2 ) 被合成并通过红外光谱和元素分析进行​​表征。BMEP-1和BMEP-2的晶体结构通过单晶X射线衍射确定。值得注意的是，这些配合物呈现出不同的金属-有机框架。BMEP-1的热行为和通过差示扫描量热法和热重分析测量研究了BMEP-2 。由于它们的大配位键和三维互连结构，这些双金属配合物表现出高热稳定性（348.0°C 和 331.0°C）。通过TGA-DSC、TGA-FTIR和非等温动力学分析研究了BMEP-1和BMEP-2对高氯酸铵热分解的催化性能。结果表明，BMEP-1和BMEP-2在高氯酸铵的热分解中表现出优异的催化性能。值得注意的是，在302.6 ℃和318
• Efficient Procedure for High-Yield Synthesis of 4-Substituted 3,5-Dinitropyrazoles Using 4-Chloro-3,5-dinitropyrazole
  作者：Igor Dalinger、Irina Vatsadze、Tatyana Shkineva、Galina Popova、Svyatoslav Shevelev

  DOI：10.1055/s-0031-1291134

  日期：2012.7

  The transformations of readily available 4-chloro-3,5-dinitropyrazole and its N-methylated derivative under the action of anionic S-/O-nucleophiles and neutral N-nucleophiles were studied. Independent of the substrate's charge (anionic, R = H, or neutral, R = Me), the nucleophilic substitution proceeds exclusively at position 4 replacing the chlorine nucleofuge. As a result of this study, the effective synthetic method for the preparation of 4-substituted 3,5-dinitropyrazoles via the nucleophilic substitution in 4-chloro3,5-dinitropyrazole was elaborated.