1-(2-nitratoethyl)-5-(nitroimino)tetrazole | 1135076-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-nitratoethyl)-5-(nitroimino)tetrazole
• 英文别名: 1-(2-nitratoethyl)-5-nitriminotetrazole
• CAS: 1135076-62-8
• 化学式: C₃H₅N₇O₅
• 分子量: 219.117
• InChiKey: GCLKBXFOEGVBRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.09
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  154.37
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2-nitratoethyl)-5-(nitroimino)tetrazole 在 羟胺 作用下， 以 水 为溶剂， 反应 0.08h， 以92%的产率得到
  参考文献：
  名称：

  1-Nitratoethyl-5-nitriminotetrazole derivatives – Shaping future high explosives

  摘要：

  1-(2-Nitratoethyl)-5-nitriminotetrazole (2) was formed by the reaction of 1-(2-hydroxyethyl-5-aminotetrazole (1) and 100% HNO3. Compound 1 was obtained by alkylation of 5-amino-1H-tetrazole. Next to the known byproduct 1-(2-hydroxyethyl)-5-nitriminotetrazole (3), a second one, 1-(2-nitratoethyl)-5-aminotetrazolium nitrate (4) was obtained and fully characterized. Nitrogen-rich salts such as the ammonium (5), hydroxylammonium (6), guanidinium (7), aminoguanidinium (8), diaminoguanidinium (9) and triaminoguanidinium (10) 1-(2-nitratoethyl)-5-nitriminotetrazolate were prepared by deprotonation or metathesis reactions. The reaction of 2 and diaminourea yielded 1-(2-nitratoethyl)-5-aminotetrazole (11). Compounds 4-11 were fully characterized by single crystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis and DSC measurements. The heats of formation of 5-10 were calculated by the atomization method based on CBS-4M enthalpies. Regarding the possible application of these compounds as energetic materials or high explosives, several detonation parameters such as the detonation pressure, velocity, energy and temperature were computed using the EXPLO5 code and the X-ray densities as well as the computed heats of formation. In addition the sensitivities towards impact, friction and electrical discharge were tested using the BAM drophammer, a friction tester as well as a small scale electrical discharge device. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.05.042
• 作为产物：
  描述：

  1-(2-氯乙基)四唑-5-胺 在 硝酸 作用下， 以45%的产率得到1-(2-nitratoethyl)-5-(nitroimino)tetrazole
  参考文献：
  名称：

  New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles

  摘要：

  AbstractA new way to make a bang: Several functionalized 1‐ethyl‐5‐aminotetrazoles, 1‐ethyl‐5‐nitrimino‐tetrazoles, and copper complexes have been synthesized and their chemical and energetic properties have been comprehensively characterized. The compounds belong to all classes of “energetic materials”: explosives, propellants, and pyrotechnics.magnified imageAlkylation of 5‐aminotetrazole (1) with 2‐chloroethanol leads to a mixture of the N‐1 and N‐2 isomers of (2‐hydroxyethyl)‐5‐aminotetrazole. Treatment of 1‐(2‐hydroxyethyl)‐5‐aminotetrazole (2) with SOCl2 yielded 1‐(2‐chlorethyl)‐5‐aminotetrazole (3). 1‐(2‐Azidoethyl)‐5‐aminotetrazole (4) was generated by the reaction of 3 with sodium azide. Nitration of 2, 3, and 4 with HNO3 (100 %) yielded in the case of 2 and 3 1‐(2‐hydroxyethyl)‐5‐nitriminotetrazole (5) and 1‐(2‐chloroethyl)‐5‐nitriminotetrazole (6). In the case of 4, 1‐(2‐nitratoethyl)‐5‐nitriminotetrazole monohydrate (7) was obtained. 1‐(2‐Azidoethyl)‐5‐nitriminotetrazole (8) could be obtained by nitration of 4 with NO2BF4 via the formation of potassium 1‐(2‐azidoethyl)‐5‐nitriminotetrazolate (9). The reaction of 6 with NaN3 resulted in the formation of the salt sodium 1‐(2‐chloroethyl)‐5‐nitriminotetrazolate (10 a). The deprotonation reaction of 6 was further investigated by the formation of the ammonium salt (10 b). The protonation of 2 and 4 with dilute nitric acid led to 1‐(2‐hydroxyethyl)‐5‐aminotetrazolium nitrate (11) and 1‐(2‐azidoethyl)‐5‐aminotetrazolium nitrate (12), respectively. Similarly, protonation of 4 with perchloric acid led to 1‐(2‐azidoethyl)‐5‐aminotetrazolium perchlorate monohydrate (13). Since 5‐nitrimino‐tetrazoles can be used as bidentate ligands, the coordination abilities of 5, 6, and 8 were tested by the reaction with copper nitrate trihydrate, yielding the copper complexes trans‐[diaquabis{1‐(2‐hydroxyethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] (14), trans‐[diaquabis{1‐(2‐chloroethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] dihydrate (15), and [diaquabis{1‐(2‐azidoethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] (16). All compounds were characterized by low‐temperature single‐crystal X‐ray diffraction. In addition, comprehensive characterization (IR, Raman, and multinuclear NMR spectroscopy (1H, 13C), elemental analysis, mass spectrometry, DSC) was performed. The heats of formation of selected compounds were computed by using heats of combustion obtained by bomb calorimetry or calculated by the atomization method. With these values and the densities determined from X‐ray crystallography, several detonation parameter were calculated by the EXPLO5 program. Finally, the sensitivities towards impact and friction were determined using a BAM drop hammer and friction tester.

  DOI：

  10.1002/chem.200802203

文献信息

• Energetic Mono-, Di-, and Trisubstituted Nitroiminotetrazoles
  作者：Young-Hyuk Joo、Jean'ne M. Shreeve

  DOI：10.1002/anie.200804755

  日期：2009.1.5

  with 100 % nitric acid and were fully characterized by spectroscopic methods, elemental analysis, and in some cases X‐ray diffraction (see example; N blue, O red). The heats of formation of these energetic materials were calculated, as well as their detonation pressures and velocities.

  大量能量：标题化合物是由氨基四唑（由叠氮化氰与伯胺反应制得）通过用100％硝酸处理而以高收率合成的，并通过光谱法，元素分析和在某些情况下X进行了全面表征射线衍射（请参见示例； N蓝色，O红色）。计算了这些高能材料的形成热，以及它们的爆炸压力和速度。