5,5'-dinitro-2H,2'H-3,3'-bipyrazole

• 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: 5,5'-dinitro-2H,2'H-3,3'-bipyrazole
• 英文别名: 5-nitro-3-(5-nitro-1H-pyrazol-3-yl)-1H-pyrazole
• 化学式: C₆H₄N₆O₄
• 分子量: 224.136
• InChiKey: ROYNNMFNYYKTHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-dinitro-2H,2'H-3,3'-bipyrazole 在 硫酸 、 硝酸 作用下， 反应 12.0h， 以95%的产率得到4,4',5,5'-tetranitro-2H,2'H-3,3'-bipyrazole
  参考文献：
  名称：

  Synthesis of 4,4'-dinitro-1H,1'H-[3,3'-bipyrazole]-5,5'-diamine

  摘要：

  All of the synthetically accessible symmetric tetranitro-3,3'-bipyrazoles were prepared. On their basis, a method was developed for the synthesis of 4,4'-dinitro-1H, 1'H-[3,3'-bipyrazole]-5,5'-diamine and its nitration was studied.

  DOI：

  10.1007/s10593-018-2336-5
• 作为产物：
  描述：

  1,4-bis-ethoxymethylen-2,3-butanedione 在 硝酸 、 乙酸酐 、 对甲苯磺酸 、 一水合肼 作用下， 以 四氢呋喃 、 苯甲腈 为溶剂， 反应 35.0h， 生成 5,5'-dinitro-2H,2'H-3,3'-bipyrazole
  参考文献：
  名称：

  通过3,3'-联吡唑部分上的硝基基团改组的多用途含能材料

  摘要：

  通过使用各种硝化条件，合成了具有C-NO 2 / N-NO 2官能团的3,3'-联吡唑基高能化合物。与相应的硝基吡唑类似物相比，联吡唑的这些硝基衍生物具有更高的密度和能量，同时保持了所需的热稳定性和敏感性。根据高能硝基基团（C-NO 2 / N-NO 2）的数量和性质，获得了不同种类的高能材料，例如绿色初级炸药，高性能二级炸药和耐热炸药。所有化合物均通过IR，NMR [ 1 H，13 C { 1 H}，15 N]，元素分析和差示扫描量热法（DSC）。还通过单晶X射线衍射研究对四个结构进行了表征。分别使用高斯03和EXPLO5 v6.01程序计算了地层热和爆轰性能。

  DOI：

  10.1002/chem.201804418

文献信息

• Multipurpose Energetic Materials by Shuffling Nitro Groups on a 3,3′‐Bipyrazole Moiety
  作者：Dheeraj Kumar、Yongxing Tang、Chunlin He、Gregory H. Imler、Damon A. Parrish、Jean'ne M. Shreeve

  DOI：10.1002/chem.201804418

  日期：2018.11.22

  family of 3,3′‐bipyrazole‐based energetic compounds having C‐NO2/N‐NO2 functionalities was synthesized by using various nitrating conditions. These nitro derivatives of bipyrazole are significantly more dense and energetic compared to the corresponding nitropyrazole analogues while maintaining the desired thermal stability and sensitivity. Depending on the number and nature of energetic nitro groups (C‐NO2/N‐NO2)

  通过使用各种硝化条件，合成了具有C-NO 2 / N-NO 2官能团的3,3'-联吡唑基高能化合物。与相应的硝基吡唑类似物相比，联吡唑的这些硝基衍生物具有更高的密度和能量，同时保持了所需的热稳定性和敏感性。根据高能硝基基团（C-NO 2 / N-NO 2）的数量和性质，获得了不同种类的高能材料，例如绿色初级炸药，高性能二级炸药和耐热炸药。所有化合物均通过IR，NMR [ 1 H，13 C 1 H}，15 N]，元素分析和差示扫描量热法（DSC）。还通过单晶X射线衍射研究对四个结构进行了表征。分别使用高斯03和EXPLO5 v6.01程序计算了地层热和爆轰性能。
• Investigation of the alkylation of nitroazoles with ?-haloketones by13C,15N, and14N NMR
  作者：V. V. Semenov、B. I. Ugrak、S. A. Shevelev、M. I. Kanishchev、A. T. Baryshnikov、A. A. Fainzil'berg

  DOI：10.1007/bf00961497

  日期：1990.8

  General methods have been worked out for the alkylation of nitroazoles with bromoacetone, bromoacetophenone, and diazoacetone in homogeneous media and by phase-transfer catalysis. The structures of the N-acetonylazoles were established by C-13, N-15, and N-14 high-resolution NMR spectroscopy.
• Balancing Excellent Performance and High Thermal Stability in a Dinitropyrazole Fused 1,2,3,4-Tetrazine
  作者：Yongxing Tang、Dheeraj Kumar、Jean’ne M. Shreeve

  DOI：10.1021/jacs.7b08789

  日期：2017.10.4

  The key to successfully designing highperformance and insensitive energetic compounds for practical applications is through adjusting the molecular organization including both fuel and oxidizer. Now a superior hydrogen -free 5/6/5 fused ring energetic material, 1,2,9,10-tetranitrodipyrazolo[1,5-d:5',1'-f][1,2,3,4]tetrazine (6) obtained from 4,4',5,5'-tetranitro-2H,21H3,3'-bipyrazole (4) by N-amination and N-azo coupling reactions is described. The structures of 5 and 6 were confirmed by single crystal X-ray diffraction measurements. Compound 6 has a remarkable room temperature experimental density of 1.955 g cm(-3) and shows excellent detonation performance. In addition, it has a high decomposition temperature of 233 degrees C. These fascinating properties, which are comparable to those of CL-20, make it very attractive in high performance applications.
• CEMEHOB, V. V.;UGRAK, B. I.;SHEVELEV, S. A.;KANISHCHEV, M. I.;BARYSHNIKOV+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 1827-1836
  作者：CEMEHOB, V. V.、UGRAK, B. I.、SHEVELEV, S. A.、KANISHCHEV, M. I.、BARYSHNIKOV+

  DOI：——

  日期：——
• Synthesis of 4,4'-dinitro-1H,1'H-[3,3'-bipyrazole]-5,5'-diamine
  作者：Tatyana K. Shkineva、Alexandr V. Kormanov、Valeriya N. Boldinova、Irina A. Vatsadze、Igor L. Dalinger

  DOI：10.1007/s10593-018-2336-5

  日期：2018.7

  All of the synthetically accessible symmetric tetranitro-3,3'-bipyrazoles were prepared. On their basis, a method was developed for the synthesis of 4,4'-dinitro-1H, 1'H-[3,3'-bipyrazole]-5,5'-diamine and its nitration was studied.