5-nitrotetrazole | 55011-46-6

• 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-nitrotetrazole
• 英文别名: 5-nitro-1H-tetrazole；5-nitro-2H-tetrazole
• CAS: 55011-46-6
• 化学式: CHN₅O₂
• 分子量: 115.051
• InChiKey: ZGZLYKUHYXFIIO-UHFFFAOYSA-N

物化性质

• 沸点：
  215.27°C (rough estimate)
• 密度：
  1.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitrotetrazole 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 sodium 5-nitrotetrazolate
  参考文献：
  名称：

  四唑与 1-卤甲基-2-甲氧基二氮烯 1-氧化物的烷基化

  摘要：

  开发了2-甲氧基二氮烯1-氧化物的卤甲基衍生物的合成。结果表明，四唑盐与溴甲基和碘甲基衍生物的烷基化在四唑环的1和2位上得到两种异构体的混合物。5-硝基四唑的烷基化选择性地在四唑环的N(2)位提供异构体。

  DOI：

  10.1007/s11172-023-3938-3
• 作为产物：
  描述：

  sodium 5-nitrotetrazolate 在 硫酸 、 水 作用下， 以63%的产率得到5-nitrotetrazole
  参考文献：
  名称：

  Koldobskii; Soldatenko; Gerasimova, Russian Journal of Organic Chemistry, 1997, vol. 33, # 12, p. 1771 - 1783

  摘要：

  DOI：

文献信息

• Neutral 5-nitrotetrazoles: easy initiation with low pollution
  作者：Thomas M. Klapötke、Carles Miró Sabaté、Jörg Stierstorfer

  DOI：10.1039/b812529e

  日期：——

  5-Nitro-2H-tetrazole (1), 1-methyl-5-nitrotetrazole (2) and 2-methyl-5-nitrotetrazole (3) were synthesized starting from the corresponding 5-amino-substituted tetrazoles in good yields and purities. The compounds were fully characterized by analytical and spectroscopic methods and their solid state structures were determined by low temperature X-ray diffraction techniques. Due to the potential of tetrazoles as energetic materials an extensive computational study (CBS-4M) was performed in order to estimate the energies of formation (ΔfU°) of the molecules, which are highly endothermic (1, 2527 kJ kg−1; 2, 2253 kJ kg−1 and 3, 2006 kJ kg−1). The EXPLO5 software was used to calculated the corresponding detonation velocities (Ddet) and detonation pressures (pdet) (1, Ddet = 9457 m s−1 and pdet = 390 kbar; 2, Ddet = 8085 m s−1 and pdet = 257 kbar and 3, Ddet = 8109 m s−1 and pdet = 262 kbar) by combining the ΔfU° values of the materials with the (X-ray calculated) densities and molecular formulas, giving performances comparable to commonly used secondary explosives (e.g., RDX). Lastly, all three neutral compounds can be easily initiated by impact (<2 J) and with high detonation velocities and excellent combined oxygen and nitrogen contents offer a more powerful and environmentally friendly alternative to commonly used primary explosives in initiating devices.

  5-硝基-2H-四唑(1)、1-甲基-5-硝基四唑(2)和2-甲基-5-硝基四唑(3)从相应的5-氨基取代四唑开始，以良好的产率和纯度被合成。这些化合物通过分析和光谱方法进行全面表征，并通过低温X射线衍射技术确定了它们的固态结构。由于四唑作为高能量材料具有很大的潜能，因此进行了全面的计算研究(CBS-4M)，以估计这些分子的生成能量（ΔfU°），这些能量具有很高的放热性（1，2527 kJ kg−1；2，2253 kJ kg−1；3，2006 kJ kg−1）。使用EXPLO5软件结合材料的ΔfU°值、（X射线计算的）密度和分子式，计算了相应的爆速（Ddet）和爆压（pdet）（1，Ddet = 9457 m s−1 和 pdet = 390 kbar；2，Ddet = 8085 m s−1 和 pdet = 257 kbar；3，Ddet = 8109 m s−1 和 pdet = 262 kbar），其性能与常用的次级炸药（例如RDX）相当。最后，所有三种中性化合物都可以通过冲击（<2 J）轻松引发，并且由于具有高爆速和出色的氧氮组合含量，为起爆装置提供了比常用初级炸药更强大且更环保的替代品。
• Comparative Studies of Cathodically-Promoted and Base-Catalyzed Michael Addition Reactions of Levoglucosenone
  作者：Alexander V. Samet、Murat E. Niyazymbetov、Victor V. Semenov、Andrei L. Laikhter、Dennis H. Evans

  DOI：10.1021/jo961019g

  日期：1996.1.1

  Regioselective Michael addition of nitro and heterocyclic compounds to levoglucosenone, 1, is effectively catalyzed by amines and also by cathodic electrolysis. In comparison to the base-catalyzed reaction, it was found that under electrochemical conditions the reaction proceeds under milder conditions and with higher yields. Cathodically-initiated Michael addition of thiols to levoglucosenone using small currents

  硝基和杂环化合物向左葡糖醛酮1的区域选择性迈克尔加成反应可通过胺和阴极电解有效地催化。与碱催化的反应相比，发现在电化学条件下反应在较温和的条件下以较高的产率进行。在几种情况下，使用小电流通过阴极引发的迈克尔将硫醇迈克尔加成到左葡萄糖苷中，会产生以前未知的苏式加成产物。当使用大电流时，倾向于形成正常的赤型异构体，即动力学产物。相反，缓慢，低电流的电解促进了这两种形式的平衡，因此赤型可以通过逆向反应和重新沉淀转化为苏式。还报道了将2-萘硫醇加到（R）-（+）-apoverbenone中。
• Energetic salts based on 1-amino-1,2,3-triazole and 3-methyl-1-amino-1,2,3-triazole
  作者：Qiu-Han Lin、Yu-Chuan Li、Ya-Yu Li、Zhu Wang、Wei Liu、Cai Qi、Si-Ping Pang

  DOI：10.1039/c1jm14322k

  日期：——

  High-density energetic salts that contain nitrogen-rich anions and the 1-amino-1,2,3-triazole (ATZ) or 3-methyl-1-amino-1,2,3-triazole (MAT) cation were synthesized. All salts were fully characterized by IR spectroscopy, multinuclear (1H, 13C) NMR spectroscopy, differential scanning calorimetry (DSC), and impact sensitivity. 1-Amino-1,2,3-triazolium 5-nitrotetrazolate, 3-methyl-1-amino-1,2,3-triazolium 5-nitrotetrazolate, and 3-methyl-1-amino-1,2,3-triazolium azotetrazolate crystallize in the triclinic space group P, as determined by single-crystal X-ray diffraction. Their densities are 1.688, 1.588, and 1.550 g cm−3, respectively. The measured densities of the other organic energetic salts range between 1.56 and 1.86 g cm−3. The detonation pressure (P) values calculated for these salts range from 21.2 to 37.3 GPa, and the detonation velocities (D) range from 7239 to 9082 m s−1, making the salts potentially energetic materials.

  合成了含有富氮阴离子的高密度能量盐及1-氨基-1,2,3-三氮唑（ATZ）或3-甲基-1-氨基-1,2,3-三氮唑（MAT）阳离子。所有盐都通过红外光谱、核磁共振（1H、13C）光谱、差示扫描量热法（DSC）和冲击敏感性进行了完全表征。1-氨基-1,2,3-三氮唑鎓5-硝基四氮唑盐、3-甲基-1-氨基-1,2,3-三氮唑鎓5-硝基四氮唑盐和3-甲基-1-氨基-1,2,3-三氮唑鎓氮四氮唑盐在单晶X射线衍射的测定下结晶于三斜空间群P。它们的密度分别为1.688、1.588和1.550 g cm−3。其他有机能量盐的测得密度在1.56到1.86 g cm−3之间。这些盐的计算爆轰压力（P）值范围为21.2到37.3 GPa，爆轰速度（D）范围为7239到9082 m s−1，使得这些盐具有潜在的能量材料特性。
• High-performing stable green replacements for ammonium perchlorate
  申请人：University of Southern California

  公开号：US09309266B2

  公开（公告）日：2016-04-12

  A highly energetic, high-oxygen carrier suitable as high-performing green replacement for ammonium perchlorate includes halogen-free ionic salts consisting of fuel cations and over-oxidized anions containing multiple nitro- or nitromethyl-substituted azolyl ligands. The over-oxidized anions include a central atom selected from the group consisting of boron, aluminum, or gallium. Characteristically, the carrier has sufficient amounts of oxygen for complete or near complete combustion of the over-oxidized anions, the fuel cations, metal additives and binders.

  一种高能量、高氧载体，适用于取代高氯酸铵的高性能绿色替代品，包括由燃料阳离子和含有多个硝基或硝基甲基取代的氮杂环配体的过氧化阴离子组成的无卤离子盐。 过氧化阴离子包括从硼、铝或镓组成的中心原子。 该载体具有足够的氧气量，可用于完全或接近完全燃烧过氧化阴离子、燃料阳离子、金属添加剂和粘合剂。
• Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5‐Dimethylpyrazol‐1‐yl‐substituted‐1,2,4,5‐tetrazines
  作者：Christopher J. Snyder、David E. Chavez、Gregory H. Imler、Edward F. C. Byrd、Philip W. Leonard、Damon A. Parrish

  DOI：10.1002/chem.201704394

  日期：2017.11.21

  Exploding Crystals! 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines readily react with energetic molecules resulting in the formation of new cocrystalline energetic materials. The quick and easy synthesis is facilitated by strong hydrogen-bonding to the dimethylpyrazolyl group and the new materials have lower sensitivities than their parents energetic compounds.

  爆炸的水晶！3,5-二甲基吡唑-1-基-取代的1,2,4,5-四嗪容易与高能分子反应，导致形成新的共晶高能材料。牢固的氢键与二甲基吡唑基之间的氢键促进了快速，简便的合成，新材料的敏感性低于其母体含能化合物。