N-(4H-1,2,4-triazol-4-yl)nitramide | 52096-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(4H-1,2,4-triazol-4-yl)nitramide
• 英文别名: 1,2,4-triazolium 4-nitrimide；4-nitroamino-1,2,4-triazole；N-4H-1,2,4-Triazol-4-ylnitramide；N-(1,2,4-triazol-4-yl)nitramide
• CAS: 52096-16-9
• 化学式: C₂H₃N₅O₂
• 分子量: 129.078
• InChiKey: JCKJLFCLEVXHNE-UHFFFAOYSA-N

物化性质

• 沸点：
  239.09°C (rough estimate)
• 密度：
  1.7860 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  癸基溴 、 N-(4H-1,2,4-triazol-4-yl)nitramide 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到1-decyl-1,2,4-triazol-1-io-4-N-nitroimide
  参考文献：
  名称：

  摘要：

  Nitration of 4-amino-1,2,4-triazole with nitric acid in acetic anhydride gives the corresponding N-nitroamino derivative which has an inner salt structure. Its alkylation with alkyl halides, as well as with oxiranes, occurs only at the endocyclic nitrogen atom, while the exocyclic reaction center is not involved. All the I-substituted products have the structure of 1-alkyl-1,2,4-triazol-1-io-4-N-nitroimides.

  DOI：

  10.1023/a:1021616232356
• 作为产物：
  描述：

  4-氨基-1,2,4-三氮唑 在 硫酸 、 硝酸 作用下， 反应 1.5h， 以63%的产率得到N-(4H-1,2,4-triazol-4-yl)nitramide
  参考文献：
  名称：

  Cu(I)-Catalyzed Regioselective Synthesis of Pyrazolo[5,1-c]-1,2,4-triazoles

  摘要：

  Cycloadditions of terminal alkynes to 1,2,4-triazolium N-imides in the presence of base and Cu(I) afford pyrazolo[5,1-c]-1,2,4-triazoles regioselectively. The scope of alkynes, the influence of the electronic nature of the leaving group, and variations in the 1-alkyl substituent were examined. Quantum chemical calculations were employed to explain the distinct reactivity of the propiolates.

  DOI：

  10.1021/jo300611a

文献信息

• Nitrogen-Rich Salts Based on Energetic Nitroaminodiazido[1,3,5]triazine and Guanazine
  作者：Yangen Huang、Yanqiang Zhang、Jean'ne M. Shreeve

  DOI：10.1002/chem.201002363

  日期：2011.2.1

  Highly dense nitrogen‐rich ionic compounds are potential high‐performance energetic materials for use in military and industrial venues. Guanazinium salts with promising energetic anions and a family of energetic salts based on nitrogen‐rich cations and the 6‐nitroamino‐2,4‐diazido[1,3,5]triazine anion (NADAT) were prepared and fully characterized by elemental analysis, IR spectroscopy, 1H NMR and

  高密度的富氮离子化合物是潜在的高性能高能材料，可用于军事和工业场所。制备了具有前途高能阴离子的胍盐和基于富氮阳离子和6-硝基氨基-2,4-二叠氮基[1,3,5]三嗪阴离子（NADAT）的高能盐家族，并通过元素分析对其进行了全面表征，红外光谱，1 H NMR和13 C NMR光谱以及差示扫描量热法（DSC）。中性NADAT（2）及其双胍盐5的晶体结构是通过单晶X射线衍射确定的（2：斜方晶系，Pnma ; 5：单斜晶系，P 21）。此外，通过质子去耦的13 C和15 N NMR光谱研究了溶液中2的异构化行为。所有这些新盐都表现出理想的物理性能，例如相对较高的密度（1.63–1.78 g cm -3）和适度的热稳定性（T d对于3 – 10为130–196°C，对于11 – 15为209–257°C ）。理论性能计算（高斯03和Cheetah 5.0），得到的离子化合物爆轰压力和速度3 - 15在21
• Synthesis of 1,2,4-triazolium 4-nitrimides with polyfunctionalized substituents
  作者：O. P. Shitov、V. L. Korolev、V. A. Tartakovsky

  DOI：10.1007/s11172-009-0326-6

  日期：2009.11

  Methods for the synthesis of 1,2,4-triazolium 4-nitrimides with nitraminoalkyl-, hetaryl-methyl, nitro ether, and dinitroalkyl substituents are developed. These compounds are useful models for evaluation of the effect of relative positions of the nitro groups on the properties of substances.

  开发了1,2,4-三氮唑鎓4-硝基亚胺与硝基氨基烷基、杂芳基甲基、硝基醚和二硝基烷基取代基的合成方法。这些化合物是评估硝基基团相对位置对物质性质的影响的有用模型。
• Synthetic routes towards tetrazolium and triazolium dinitromethylides
  作者：A. R. Katritzky、G. L. Sommen、A. V. Gromova、R. M. Witek、P. J. Steel、R. Damavarapu

  DOI：10.1007/s10593-005-0116-5

  日期：2005.1
• ——
  作者：T. P. Kofman、G. Yu. Kartseva、M. B. Shcherbinin

  DOI：10.1023/a:1021616232356

  日期：——

  Nitration of 4-amino-1,2,4-triazole with nitric acid in acetic anhydride gives the corresponding N-nitroamino derivative which has an inner salt structure. Its alkylation with alkyl halides, as well as with oxiranes, occurs only at the endocyclic nitrogen atom, while the exocyclic reaction center is not involved. All the I-substituted products have the structure of 1-alkyl-1,2,4-triazol-1-io-4-N-nitroimides.
• Cu(I)-Catalyzed Regioselective Synthesis of Pyrazolo[5,1-<i>c</i>]-1,2,4-triazoles
  作者：Davit Jishkariani、C. Dennis Hall、Alexander A. Oliferenko、David Leino、Alan R. Katritzky

  DOI：10.1021/jo300611a

  日期：2012.7.6

  Cycloadditions of terminal alkynes to 1,2,4-triazolium N-imides in the presence of base and Cu(I) afford pyrazolo[5,1-c]-1,2,4-triazoles regioselectively. The scope of alkynes, the influence of the electronic nature of the leaving group, and variations in the 1-alkyl substituent were examined. Quantum chemical calculations were employed to explain the distinct reactivity of the propiolates.