1-(2-hydroxyethyl)-5-nitriminotetrazole | 1334230-66-8

• 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-hydroxyethyl)-5-nitriminotetrazole
• CAS: 1334230-66-8
• 化学式: C₃H₆N₆O₃
• 分子量: 174.119
• InChiKey: NPKNPPGLXIBXAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.31
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  122.23
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyethyl)-5-nitriminotetrazole 在 氨 作用下， 以 水 为溶剂， 反应 0.08h， 以82%的产率得到ammonium 1-(2-hydroxyethyl)-5-nitriminotetrazole
  参考文献：
  名称：

  1-(2-羟乙基)-5-硝基四唑的高能富氮盐

  摘要：

  1-(2-羟乙基)-5-硝基四唑(2)是由5-氨基-1-(2-羟乙基)四唑(1)和100％HNO3反应形成的。通过用2-氯乙醇将5-氨基-1H-四唑烷基化得到化合物1。富氮盐，例如铵 (3)、羟铵 (4)、胍 (5)、氨基胍 (6)、二氨基胍 (7)、三氨基胍 (8)、叠氮甲脒 (9) 和二氨基脲 (10) 1-( 2-羟乙基)-5-硝基四唑酸盐通过去质子化或复分解反应制备。通过单晶 X 射线衍射（9 和 10 除外）、振动光谱（IR 和拉曼）、多核 NMR 光谱、元素分析和差示扫描量热法 (DSC) 测量对化合物 3-10 进行了全面表征。4-10 的形成热是通过基于 CBS-4M 焓的雾化方法计算的。利用这些值和 X 射线密度，使用 EXPLO5 代码计算了几个爆震参数，例如爆震压力、速度、能量和温度。此外，还使用 ​​BAM 落锤、摩擦测试仪和小型放电装置测试了它们对冲击、摩擦和放电的敏感性。

  DOI：

  10.1002/ejic.201100535
• 作为产物：
  描述：

  2-(5-氨基四唑-1-基)乙醇 在 硝酸 作用下， 以95%的产率得到1-(2-hydroxyethyl)-5-nitriminotetrazole
  参考文献：
  名称：

  1-(2-羟乙基)-5-硝基四唑的高能富氮盐

  摘要：

  1-(2-羟乙基)-5-硝基四唑(2)是由5-氨基-1-(2-羟乙基)四唑(1)和100％HNO3反应形成的。通过用2-氯乙醇将5-氨基-1H-四唑烷基化得到化合物1。富氮盐，例如铵 (3)、羟铵 (4)、胍 (5)、氨基胍 (6)、二氨基胍 (7)、三氨基胍 (8)、叠氮甲脒 (9) 和二氨基脲 (10) 1-( 2-羟乙基)-5-硝基四唑酸盐通过去质子化或复分解反应制备。通过单晶 X 射线衍射（9 和 10 除外）、振动光谱（IR 和拉曼）、多核 NMR 光谱、元素分析和差示扫描量热法 (DSC) 测量对化合物 3-10 进行了全面表征。4-10 的形成热是通过基于 CBS-4M 焓的雾化方法计算的。利用这些值和 X 射线密度，使用 EXPLO5 代码计算了几个爆震参数，例如爆震压力、速度、能量和温度。此外，还使用 ​​BAM 落锤、摩擦测试仪和小型放电装置测试了它们对冲击、摩擦和放电的敏感性。

  DOI：

  10.1002/ejic.201100535

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。
• 1-Nitratoethyl-5-nitriminotetrazole derivatives – Shaping future high explosives
  作者：Niko Fischer、Thomas M. Klapötke、Jörg Stierstorfer、Carina Wiedemann

  DOI：10.1016/j.poly.2011.05.042

  日期：2011.8

  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.
• New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles
  作者：Jörg Stierstorfer、Karina R. Tarantik、Thomas M. Klapötke

  DOI：10.1002/chem.200802203

  日期：2009.6.2

  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‐[diaquabis1‐(2‐hydroxyethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] (14), trans‐[diaquabis1‐(2‐chloroethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] dihydrate (15), and [diaquabis1‐(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.
• Energetic Nitrogen‐Rich Salts of 1‐(2‐Hydroxyethyl)‐5‐nitriminotetrazole
  作者：Niko Fischer、Thomas M. Klapötke、Jörg Stierstorfer

  DOI：10.1002/ejic.201100535

  日期：2011.10

  1-(2-Hydroxyethyl)-5-nitriminotetrazole (2) was formed by the reaction of 5-amino-1-(2-hydroxyethyl)tetrazole (1) and 100 % HNO3. Compound 1 was obtained by alkylation of 5-amino-1H-tetrazole with 2-chloroethanol. Nitrogen-rich salts such as the ammonium (3), hydroxylammonium (4), guanidinium (5), aminoguanidinium (6), diaminoguanidinium (7), triaminoguanidinium (8), azidoformamidinium (9), and diaminouronium

  1-(2-羟乙基)-5-硝基四唑(2)是由5-氨基-1-(2-羟乙基)四唑(1)和100％HNO3反应形成的。通过用2-氯乙醇将5-氨基-1H-四唑烷基化得到化合物1。富氮盐，例如铵 (3)、羟铵 (4)、胍 (5)、氨基胍 (6)、二氨基胍 (7)、三氨基胍 (8)、叠氮甲脒 (9) 和二氨基脲 (10) 1-( 2-羟乙基)-5-硝基四唑酸盐通过去质子化或复分解反应制备。通过单晶 X 射线衍射（9 和 10 除外）、振动光谱（IR 和拉曼）、多核 NMR 光谱、元素分析和差示扫描量热法 (DSC) 测量对化合物 3-10 进行了全面表征。4-10 的形成热是通过基于 CBS-4M 焓的雾化方法计算的。利用这些值和 X 射线密度，使用 EXPLO5 代码计算了几个爆震参数，例如爆震压力、速度、能量和温度。此外，还使用 ​​BAM 落锤、摩擦测试仪和小型放电装置测试了它们对冲击、摩擦和放电的敏感性。