5-amino-1-methoxy-1H-tetrazole | 1071952-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-methoxy-1H-tetrazole
• 英文别名: 1-methoxy-5-aminotetrazole；1-Methoxytetrazol-5-amine
• CAS: 1071952-87-8
• 化学式: C₂H₅N₅O
• mdl: MFCD19207941
• 分子量: 115.095
• InChiKey: DCVOFCSNJMIQAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-1-methoxy-1H-tetrazole 在 硝酸 作用下， 以35%的产率得到1-methoxy-5-nitroiminotetrazole
  参考文献：
  名称：

  高密度含能单-或双（氧）-5-亚硝基亚硝基三唑

  摘要：

  产生影响：通过叠氮化氰和烷基氧胺在100％硝酸中的反应制得的氧-5-氨基四唑（见方案）以高收率提供了一系列高能氧-5-硝基亚氨基四唑酸酯。这些化合物表现出良好的物理和爆炸特性，例如中等的热稳定性，高密度，高吸热性，良好的爆炸压力P和良好的爆炸速度D。

  DOI：

  10.1002/anie.201003866
• 作为产物：
  描述：

  1-diazo-2-methoxyguanidine 以 水 、 乙腈 为溶剂， 生成 5-amino-1-methoxy-1H-tetrazole
  参考文献：
  名称：

  1-Substituted 5-Aminotetrazoles: Syntheses from CNN₃ with Primary Amines

  摘要：

  1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate gave 1-substituted aminotetrazole in good yield. This protocol also was utilized in the syntheses of bis- and tris(1-substituted 5-aminotetrazole) derivatives.

  DOI：

  10.1021/ol8019742

文献信息

• Energetic<i>N</i>-Trinitroethyl-Substituted Mono-, Di-, and Triaminotetrazoles
  作者：Qinghua Zhang、Jiaheng Zhang、Damon A. Parrish、Jean'ne M. Shreeve

  DOI：10.1002/chem.201300994

  日期：2013.8.12

  A series of dense energetic N‐trinitroethyl‐substituted mono‐, bis‐, and tri‐5‐aminotetrazoles were obtained by reacting primary amines with in situ generated cyanogen azide, followed by the trinitroethyl functionalization that involves a condensation of a hydroxymethyl intermediate (prepared by a reaction with formaldehyde) with trinitromethane. These compounds were fully characterized by using multinuclear

  通过使伯胺与原位生成的叠氮化氰反应，然后进行三硝基乙基官能化（涉及羟甲基中间体的缩合反应，制得了一系列致密的高能N-三硝基乙基取代的单，双和三-5-氨基四唑）通过与甲醛反应）与三硝基甲烷反应。这些化合物通过多核NMR光谱，IR，元素分析，差示扫描量热法（DSC）进行了充分表征，并且在一种情况下（使用9进行单晶XRD分析）得到了充分表征。用高斯03计算所有化合物的形成热，然后与实验密度结合确定爆轰压力（P）和速度（D v）的高能材料。有趣的是，它们大多数都表现出高密度，良好的热稳定性，可接受的氧平衡，正形成热，低冲击敏感性和出色的爆震性能，这突出了它们作为令人着迷的高能材料一类的实际应用潜力。
• High-Density Energetic Mono- or Bis(Oxy)-5-Nitroiminotetrazoles
  作者：Young-Hyuk Joo、Jean'ne M. Shreeve

  DOI：10.1002/anie.201003866

  日期：——

  Making an impact: Oxy‐5‐aminotetrazoles, which were obtained from the reaction of cyanogen azide and alkyl oxyamine in 100 % nitric acid (see scheme), give a series of highly energetic oxy‐5‐nitroiminotetrazolates in good yield. These compounds exhibit good physical and detonation properties, such as moderate thermal stabilities, high densities, high endothermy, good detonation pressures P, and good

  产生影响：通过叠氮化氰和烷基氧胺在100％硝酸中的反应制得的氧-5-氨基四唑（见方案）以高收率提供了一系列高能氧-5-硝基亚氨基四唑酸酯。这些化合物表现出良好的物理和爆炸特性，例如中等的热稳定性，高密度，高吸热性，良好的爆炸压力P和良好的爆炸速度D。
• Bisnitramide-Bridged <i>N</i>-Substituted Tetrazoles with Balanced Sensitivity and High Performance
  作者：Ajay Kumar Chinnam、Richard J. Staples、Jean’ne M. Shreeve

  DOI：10.1021/acs.orglett.3c00170

  日期：2023.3.10

  a simple synthetic strategy for bridged bis(nitramide)-based N-substituted tetrazoles is described. All new compounds were isolated and fully characterized by sophisticated analytical techniques. The structures of the intermediate derivative and two final compounds were determined by single-crystal X-ray data. The structures of the intermediate derivative and two final compounds were determined by

  在这项研究中，描述了桥联双（硝酰胺）基N取代四唑的简单合成策略。所有新化合物都经过分离，并通过复杂的分析技术进行了全面表征。中间衍生物和两种最终化合物的结构由单晶 X 射线数据确定。中间衍生物和两种最终化合物的结构由单晶 X 射线数据确定。讨论了新型桥联双硝胺基N-取代四唑的热稳定性和能量特性，并与已知材料进行了比较。
• Energetic salts based on 1-methoxy-5-nitroiminotetrazole
  作者：Young-Hyuk Joo、Jin Hyuk Chung、Soo Gyeong Cho、Eun Mee Goh

  DOI：10.1039/c3nj41117f

  日期：——

  Eight new energetic salts based on 1-methoxy-5-nitroiminotetrazole, which was obtained by nitration of 1-methoxy-5-aminotetrazole, were synthesized. Guanidinium (5), aminoguanidinium (6), diaminoguanidinium (7), triaminoguanidinium (8), carbohydrazidinium (9), 3-amino-1,2,4-triazolium (10), 4-amino-1,2,4-triazolium (11), and 3,5-diamino-1,2,4-triazolium (12) salts were characterized by vibrational spectroscopy (IR, Raman), multinuclear spectroscopy (1H, 13C, 15N), elemental analysis, and single crystal X-ray diffraction analysis. Salts 5·1/3H2O and 7–9 crystallize in the triclinic space group P, whereas compounds 6 and 10 crystallize in the monoclinic space groups C2/c and P2(1)/n, respectively. Compound 11 is in orthorhombic group P2(1)2(1)2(1). In addition, the heats of formation (ΔHf), and detonation properties (pressure and velocity) were calculated using Gaussian 03 and EXPLO5 programs, respectively. Thermal stabilities were obtained by DSC measurements and the sensitivities toward impact and friction were determined by BAM methods.

  基于1-甲氧基-5-硝基亚氨基四唑的八种新型高能盐被合成，该化合物是通过对1-甲氧基-5-氨基四唑进行硝化获得的。合成的盐包括：氨基脲盐（5）、氨基氨基脲盐（6）、二氨基脲盐（7）、三氨基脲盐（8）、碳肼基脲盐（9）、3-氨基-1,2,4-三唑盐（10）、4-氨基-1,2,4-三唑盐（11）和3,5-二氨基-1,2,4-三唑盐（12）。这些盐的特性通过振动光谱（红外光谱、拉曼光谱）、多核光谱（1H、13C、15N）、元素分析以及单晶X射线衍射分析进行了表征。盐5·1/3H2O和7–9以三斜晶系P空间群结晶，而化合物6和10则分别以单斜晶系C2/c和P2(1)/n结晶。化合物11属于正交晶系P2(1)2(1)2(1)。此外，利用Gaussian 03和EXPLO5程序分别计算了生成热（ΔHf）和爆炸特性（压力和速度）。热稳定性通过DSC测量获得，而撞击和摩擦的敏感性则通过BAM方法确定。
• 1-Substituted 5-Aminotetrazoles: Syntheses from CNN₃ with Primary Amines
  作者：Young-Hyuk Joo、Jean’ne M. Shreeve

  DOI：10.1021/ol8019742

  日期：2008.10.16

  1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate gave 1-substituted aminotetrazole in good yield. This protocol also was utilized in the syntheses of bis- and tris(1-substituted 5-aminotetrazole) derivatives.