1,2-二氢-5-硝基-3H-1,2,4-三唑-3-酮 | 932-64-9

• 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
• 中文名称: 1,2-二氢-5-硝基-3H-1,2,4-三唑-3-酮
• 英文名称: 3-nitro-1,2,4-triazol-5-one
• 英文别名: s-Triazol-3-ol, 5-nitro-；3-nitro-1,4-dihydro-1,2,4-triazol-5-one
• CAS: 932-64-9
• 化学式: C₂H₂N₄O₃
• mdl: MFCD00511298
• 分子量: 130.063
• InChiKey: QJTIRVUEVSKJTK-UHFFFAOYSA-N

物化性质

• 沸点：
  240.69°C (rough estimate)
• 密度：
  1.9[at 20℃]
• 溶解度：
  20℃有机溶剂中为16.8g/L
• LogP：
  -1.699 at 22℃
• 物理描述：
  Nitrotriazolone <or> nto appears as a solid or liquid. May explode under prolonged exposure to heat or fire. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments.
• 颜色/状态：
  White to pale yellow crystalline powder
• 气味：
  Odorless
• 熔点：
  268-271 °C
• 蒸汽压力：
  3.1X10-8 mm Hg at 25 deg (est)
• 亨利常数：
  Henry's Law constant = 4.1X10-13 atm-cu m/mol at 25 °C (est)
• 分解：
  When heated to decomposition it emits toxic vapors of NOx.
• 燃烧热：
  Enthalpy of Combustion: -934.4 kJ/mol (crystal phase)
• 解离常数：
  pKa = 3.76 at 20 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 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：
  99.3
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

代谢

在当前研究中，我们合成了(14)C标记的5-硝基-1,2,4-三唑-3-酮(NTO)，并研究了地塞米松诱导的小鼠肝微粒体对其的代谢。在氮气气氛中，5-氨基-1,2,4-三唑-3-酮是NTO唯一检测到的代谢物。微粒体的硝基还原酶活性依赖于NADPH，完全被一氧化碳抑制，部分被氧气抑制。在有氧条件下，除了少量的胺之外，主要形成的代谢物是5-羟基-三唑酮，尿唑。这种化合物是NTO氧化脱硝的结果，产生了等量的亚硝酸盐。这个反应，像硝基还原酶活性一样，依赖于NADPH，并且完全被一氧化碳抑制。硝基还原和氧化脱硝都被咪唑相关抑制剂抑制：咪康唑和甲巯咪唑，以及较少程度上被N-辛基胺抑制。微粒体的脱硝作用被用糖皮质激素和苯巴比妥治疗的 rats。微粒体还原酶活性存在于未经处理的 rat 微粒体中，并且能够被各种诱导剂恢复。本研究的结果表明，细胞色素P-450在NTO的代谢中发挥作用，这一发现得到了重组细胞色素P-450系统的转化支持。

In the present study, we synthesized (14)C-labeled 5-nitro-1,2,4-triazol-3-one (NTO) and investigated its hepatic metabolism by dexamethasone-induced murine hepatic microsomes. Under the nitrogen atmosphere, 5-amino-1,2,4-triazol-3-one was the only detected metabolite of NTO. The microsomal nitroreductase activity was dependent on NADPH, totally inhibited by carbon monoxide and partially inhibited by oxygen. In aerobic conditions, beside a low amount of amine, the major metabolite formed is the 5-hydroxy-triazolone, urazole. This compound resulted from the oxidative denitrification of NTO, which produced equivalent amount of nitrite. This reaction, like the nitroreductase activity, was dependent on NADPH and totally inhibited by carbon monoxide. Both nitroreduction and oxidative denitrification were inhibited by imidazole-related inhibitors: miconazole and methimazole, and to a less extent by N-octylamine. The microsomal denitrification was induced by the treatment of rats with dexamethasone and phenobarbital. The microsomal reductase activity is present in untreated rat microsomes, and recovered with various inducers. The results of this study indicate the role played by cytochrome P-450 in the metabolism of NTO, supported by its transformation with reconstituted cytochrome P-450 systems.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在本研究中，我们调查了爆炸物5-硝基-1,2,4-三唑-3-酮（NTO）1的代谢。合成了(14)C5-和(14)C3-标记的NTO，以便阐明其细菌和哺乳动物代谢。对形成的代谢物进行了表征，并比较了降解途径。从含有高浓度爆炸物（15克/升）的工业废料中分离出地衣芽孢杆菌。NTO 1的微生物代谢通过一种对氧不敏感的硝基还原进行，导致初级胺ATO（5-氨基-1,2,4-三唑-3-酮）2，然后是三唑酮环的裂解。在pH 6且存在蔗糖的情况下，微生物硝基还原达到最大，而环裂解发生在pH 8。为了实现地衣芽孢杆菌对NTO的完全降解，需要永久控制和调整pH。三唑酮环来自“伪胍基”组（R-NH-C(NH2)=N-R'）的水解。

In the present study, we have investigated the metabolism of the explosive 5-nitro-1,2,4-triazol-3-one (NTO) 1. (14)C5- and (14)C3-labeled NTO were synthesized to facilitate the elucidation of its bacterial and mammalian metabolism. The metabolites formed were characterised, and the degradative pathways compared. The Bacillus licheniformis strain was isolated from industrial waste containing high concentrations of the explosive (15 g/L). Microbial metabolism of NTO 1 proceeded through an oxygen-insensitive nitroreduction leading to the primary amine ATO (5-amino-1,2,4,-triazol-3-one) 2, followed by cleavage of the triazolone ring. The maximum microbial nitroreduction occurred at pH 6 in the presence of sucrose, while the ring, cleavage occurred at pH 8. A permanent control and adjustment of the pH was required to achieve the complete degradation of NTO by B. licheniformis. The triazolone ring resulted from the hydrolysis of the 'pseudo guanido' group (R-NH-C(NH2)=N-R').

来源:Hazardous Substances Data Bank (HSDB)

代谢

基于体内毒性研究，有充分证据表明测试物质通过胃肠道吸收，并且较少程度通过皮肤吸收。还有证据表明，在雄性和雌性大鼠中，测试物质会系统性分布到肝脏和睾丸。肝脏可能是代谢的场所，肾脏可能是排泄的途径。在大鼠肝微粒体中，该物质发生硝基还原，形成ATO（5-氨基-1,2,4-三唑-3-酮），即一种初级胺。NTO还会发生氧化脱硝反应，生成尿唑和亚硝酸盐。

Based on in vivo toxicity studies, there is good evidence that the test substance is absorbed via the gastrointestinal tract and to a lesser extent via the skin. There is also evidence of systemic distribution to the liver in male and female rats and the testes. The liver may be a site of metabolism and the kidneys a possible route of excretion. In rat liver microsomes, the substance undergoes nitroreduction leading to the formation of ATO (5-amino-1,2,4-triazol-3-one), a primary amine. NTO also undergoes an oxidative denitrification, providing urazole and nitrite.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：硝基三唑酮（NTO）是一种撞击不敏感的炸药。人体研究：NTO在EPISKIN人体表皮皮肤构建物中引起的平均组织活力为100.3 +/- 2.8%，因此被预测为对皮肤无刺激性。NTO在分离的人红细胞中引起的变性血红蛋白形成与硝基苯相似。有报道称，当工人们呼吸NTO粉尘时，会出现喉咙刺激的情况。动物研究：家兔眼睛测试被认为是阴性的；然而，在几只动物中，测试物质的施用确实导致了短暂的结膜和角膜刺激，并且有一只发展出了慢性前葡萄膜炎。NTO在豚鼠中不是皮肤致敏剂。NTO对牛白血病病毒转化的羊肾成纤维细胞FLK细胞系的细胞毒性类似于硝基苯。在重复口服毒性测试中，NTO在大鼠中诱导了睾丸毒性和少精子症。为了评估NTO是否会产生额外的生殖和发育效果，对大鼠进行了一项修改后的延长一代生殖毒性测试。NTO没有明显影响生育力指标，包括交配指数、妊娠指数、窝大小和性别比。在P1和F1 3600毫克/升NTO雄性中观察到了生精小管退化或萎缩。F1 3600毫克/升组的雄性表现出减少的生殖器官质量（睾丸、附睾和附属性器官）。与对照组相比，NTO暴露的F1雄性乳头保留增加。与对照组相比，3600毫克/升NTO暴露的雄性青春期延迟了2.6天。NTO在鼠伤寒沙门氏菌/大肠杆菌平板掺入突变试验中无论是激活还是未激活都是阴性的。当在大鼠体内进行测试时，NTO在大鼠外周血液中不是致基因毒性的。生态毒性研究：蚯蚓暴露于1077毫克/升NTO水溶液中48小时；没有观察到死亡。

IDENTIFICATION AND USE: Nitrotriazolone (NTO) is impact-insensitive explosive. HUMAN STUDIES: NTO elicited a mean tissue viability of 100.3 +/- 2.8% using the EPISKIN human epidermis skin constructs and therefore was predicted as non-irritant to the skin. Methemoglobin formation in isolated human erythrocytes for NTO was similar to that of nitrobenzene. There are reported cases of workers with throat irritations when breathing NTO dust. ANIMAL STUDIES: The rabbit eye test was considered negative; however, transient conjunctival and corneal irritation did result from the test substance application in several animals and one developed a chronic anterior uveitis. NTO was not a skin sensitizer in guinea pigs. The bovine leukemia virus-transformed lamb kidney fibroblasts FLK cell line cytotoxicity for NTO was similar to that of nitrobenzene. NTO induced testicular toxicity and oligospermia in repeated-dose oral toxicity tests in rats. To evaluate whether NTO produces additional reproductive and developmental effects, a modified extended one-generation reproductive toxicity test was conducted in rats. NTO did not markedly affect measures of fertility, including mating indices, gestation index, litter size, and sex ratio. Seminiferous tubule degeneration or atrophy was observed in P1 and F1 3600-mg/L NTO males. F1 males in the 3600 mg/L group exhibited reduced reproductive organ mass (testes, epididymides, and accessory sex organs). Nipple retention was increased in NTO exposed F1 males compared to controls. Attainment of puberty was delayed by 2.6 d in the 3600-mg/L NTO-exposed males relative to controls. NTO was negative in the Salmonella typhimurium/Escherichia coli Plate Incorporation Mutation Assay both with and without activation. NTO was not genotoxic in rat peripheral blood when tested in vivo. ECOTOXICITY STUDIES: Earthworms were exposed to concentrations of 1077 mg/L NTO solution in water for 48 hours; no mortality was observed.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。必要时进行吸痰。观察呼吸不足的迹象，并在需要时辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时进行治疗……。监测休克，并在必要时进行治疗……。预期可能出现癫痫，并在必要时进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。/毒物A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注5%葡萄糖水（D5W），以保持开放，最小流量为/SRP: "To keep open", minimal flow rate/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。注意观察液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/CASE REPORTS/ ...报告了工人吸入NTO粉尘时喉咙受到刺激的病例。

/CASE REPORTS/ ...reported cases of workers with throat irritations when breathing NTO dust.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

基于体内毒性研究，有充分证据表明测试物质通过胃肠道吸收，并且较少程度通过皮肤吸收。还有证据表明，在雄性和雌性大鼠中，测试物质会系统性分布到肝脏和睾丸。肝脏可能是代谢的场所，肾脏可能是排泄的途径。在大鼠肝微粒体中，该物质发生硝基还原，形成ATO（5-氨基-1,2,4-三唑-3-酮），即一种初级胺。NTO还会发生氧化脱硝反应，生成尿唑和亚硝酸盐。

Based on in vivo toxicity studies, there is good evidence that the test substance is absorbed via the gastrointestinal tract and to a lesser extent via the skin. There is also evidence of systemic distribution to the liver in male and female rats and the testes. The liver may be a site of metabolism and the kidneys a possible route of excretion. In rat liver microsomes, the substance undergoes nitroreduction leading to the formation of ATO (5-amino-1,2,4-triazol-3-one), a primary amine. NTO also undergoes an oxidative denitrification, providing urazole and nitrite.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

3-硝基-1,2,4-三唑-5-酮（NTO）是不敏感弹药的组成部分，有望替代传统炸药。毒物代谢动力学数据可以帮助解释毒性研究以及种间外推，但目前关于NTO的毒物代谢动力学和代谢的资料有限。为了补充这些有限的数据，进一步在大鼠体内进行了NTO研究，并测量了血液浓度，使用计算机模拟方法估计了NTO的组织分布，并开发了大鼠和猕猴对NTO处置的生理基础药代动力学模型，并将其外推至人类。这些模型预测可以用来从大鼠毒理学研究中确定的出发点点外推，为估计NTO对人类可接受暴露水平提供科学依据。

3-Nitro-1,2,4-triazol-5-one (NTO) is a component of insensitive munitions that are potential replacements for conventional explosives. Toxicokinetic data can aid in the interpretation of toxicity studies and interspecies extrapolation, but only limited data on the toxicokinetics and metabolism of NTO are available. To supplement these limited data, further in vivo studies of NTO in rats were conducted and blood concentrations were measured, tissue distribution of NTO was estimated using an in silico method, and physiologically based pharmacokinetic models of the disposition of NTO in rats and macaques were developed and extrapolated to humans. The model predictions can be used to extrapolate from designated points of departure identified from rat toxicology studies to provide a scientific basis for estimates of acceptable human exposure levels for NTO.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  1.1D
• 海关编码：
  2933990090
• 危险类别：
  1.1

反应信息

• 作为反应物：
  描述：

  1,2-二氢-5-硝基-3H-1,2,4-三唑-3-酮 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 5.0h， 以70%的产率得到5-氨基-2,4-二氢-[1,2,4]噻唑-3-酮
  参考文献：
  名称：

  Synthesis of [3-14C]- and [5-14C]-labelled 5-nitro-1,2,4-triazol-3-one (NTO) and study of its chemical decomposition

  摘要：

  The chemical decomposition of NTO 1 and its corresponding amine ATO 2 was investigated. To make easier the identification of the decomposition products, we synthesized C-14-labelled NTO and ATO. Our results confirmed the high stability of the NTO triazolone ring. Its scission can be achieved partially by sulfuric acid under intensive heat and pressure. The triazolone ring of ATO was cleaved in alkaline solution. Carbon dioxide is evolved leaving a polar compound assumed to be aminoguanidine. The deamination of ATO was achieved by nitrosation. In dilute HCl (0.15N), 2 equivalents of NO2- lead to the triazolone: Lb, through a radical de-diazotation of the diazo intermediate. With 3 to 10 equivalents of NO2-, the nitrosation leads exclusively to the azide 6.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1203::aid-jlcr276>3.0.co;2-f
• 作为产物：
  描述：

  1,2-二氢-3H-1,2,4-三氮唑-3-酮 在 硫酸 、 硝酸 作用下， 生成 1,2-二氢-5-硝基-3H-1,2,4-三唑-3-酮
  参考文献：
  名称：

  NTO结构和振动光谱的理论和实验研究

  摘要：

  摘要 通过从头算分子轨道计算在 Hartree-Fock 确定了高爆炸药 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO) 的结构和振动光谱。和二阶 Moller-Plesset 能级和密度泛函理论 (B3LYP)。分子的实验频率已由纯 NTO 薄膜和在 21 K 下在氩基质中分离的 NTO 分子的红外光谱确定。基于 MP2/6–311G** 的计算结果获得了气相 NTO 的力场等级。此外，使用 NTO 薄膜的实验振动频率和按比例缩放的 ab initio 振动频率构建了固态 NTO 的力场。

  DOI：

  10.1016/s0022-2860(96)09343-x
• 作为试剂：
  描述：

  2,4,6-三硝基氯苯 在 1,2-二氢-5-硝基-3H-1,2,4-三唑-3-酮 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以33%的产率得到6-氯-2,4-二硝基苯酚
  参考文献：
  名称：

  Coburn, Michael D.; Lee, Kien-Yin, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 575 - 577

  摘要：

  DOI：

文献信息

• Thermally Stable Energetic Salts Composed of Heterocyclic Anions and Cations Based on 3,6,7-Triamino-7 <i>H</i> -<i>s</i> -triazolo[5,1-<i>c</i> ]-<i>s</i> -triazole: Synthesis and Intermolecular Interaction Study
  作者：Qing Ma、Guijuan Fan、Longyu Liao、Huanchang Lu、Ya Chen、Jinglun Huang

  DOI：10.1002/cplu.201700058

  日期：2017.3

  intermolecular hydrogen-bond interaction of these new salts. With the assistance of the EXPLO5 program, the detonation velocities, detonation pressures, and specific impulses of the salts were found to fall in the ranges 8113-9477 m s-1 , 24.1-31.4 GPa, and 203.2-224.2 s, respectively. The predicted detonation performance indicate that all the energetic salts based on TATT are similar to those of 1,3,5-trinitroperhydro-1

  为了建立分子间的NH⋅⋅⋅O和NH⋅⋅⋅N氢键（HB）相互作用，将一系列高能N杂环阴离子（包括多硝基和多氮阴离子）引入3,6,7-三氨基- 7 Hs-三唑并[5,1-c] -s-三唑（TATT）阳离子可得到许多新颖的高能盐。使用单晶X射线衍射确认化合物2⋅H2O，6和9的晶体结构和晶体堆积特性。此外，Hirshfeld表面分析和分子内原子拓扑分析提供了对分子间氢原子的洞察力。这些新盐的键相互作用。在EXPLO5程序的帮助下，盐的爆炸速度，爆炸压力和比冲分别落在8113-9477 m s-1、24.1-31.4 GPa和203.2-224.2 s范围内。
• Energetic π-conjugated vinyl bridged triazoles: a thermally stable and insensitive heterocyclic cation
  作者：Qing Ma、Ya chen、Longyu Liao、Huanchang Lu、Guijuan Fan、Jinglun Huang

  DOI：10.1039/c7dt01261f

  日期：——

  A new family of vinyl bridge 1,1′-(ethane-5-yl)-bis(3,4-diamino-1,2,4-triazolium) salts were explored as novel structural energetic materials. These new salts were further characterized by elemental analysis, infrared and multinuclear NMR spectra. Structural confirmation of nine salts such as 4–11 and 14 was supported by single-crystal X-ray diffraction. Theoretical investigations associated with heats

  探索了新的乙烯基桥1,1'-（乙烷-5-基）-双（3,4-二氨基-1,2,4-三唑鎓）盐家族，作为新型结构含能材料。这些新的盐通过元素分析，红外和多核NMR光谱进一步表征。单晶X射线衍射支持9种盐（如4-11和14）的结构确认。分别采用高斯09程序和EXPLO5 V6.02代码进行了与地层热和爆轰性能相关的理论研究。使用BAM标准研究了对冲击和摩擦的敏感性。根据实验和计算数据，这些盐的密度范围为1.61至1.82 g cm -3在298 K下，良好的热稳定性（T d：217°C–322°C），出色的爆震性能（P：7809 ms -1至9640 ms -1，D：24.6 GPa–33.9 GPa）以及合理的冲击和摩擦敏感性（IS：4 J至60 J，FS：120 N至360 N）。
• 草酰肼的5-硝基-1,2,4-三唑-5-酮盐化合物
  申请人：西安近代化学研究所

  公开号：CN105272929A

  公开（公告）日：2016-01-27

  本发明公开了一种草酰肼的5-硝基-1,2,4-三唑-5-酮盐化合物，其结构式如(I)所示：本发明主要用于炸药、推进剂和烟火技术领域。
• Insight into the thermostability and low sensitivity of energetic salts based on planar fused-triazole cation
  作者：Chengming Bian、Qunying Lei、Ji Zhang、Xiang Guo、Zhinan Ma、Haikuan Yang、Hongli Li、Zhongliang Xiao

  DOI：10.1016/j.poly.2021.115158

  日期：2021.6

  A new family of nitrogen-rich fused-triazole energetic salts based on 3,6-diamino-1H-[1,2,4]triazolo[4,3-b][1,2,4]triazole were synthesized and fully characterized by infrared spectroscopy (IR), 1H and 13C nuclear magnetic resonance, elemental analysis, differential scanning calorimetry (DSC). Structures of 3 and 4·H2O were confirmed by single-crystal X-ray diffraction analyses and their crystal packing

  合成了基于3,6-二氨基-1H- [1,2,4]三唑[4,3-b] [1,2,4]三唑的富氮稠合三唑高能盐家族红外光谱（IR），1 H和13 C核磁共振，元素分析，差示扫描量热法（DSC）。通过单晶X射线衍射分析确认了3和4 ·H 2 O的结构，并充分分析了它们的晶体堆积特性。所有新化合物均显示出良好的热稳定性（T d  > 223°C），并且对外部机械刺激不敏感。这些盐的密度为1.72至1.93 g cm -3。理论性能计算（Gaussian 09和EXPLO 5）分别提供了20.8至32.9 GPa和7599至8719 m s -1范围内的爆震压力和速度。高氯酸盐3表现出最高的密度（1.93 g cm -3）和最佳的氧平衡（-30.0％），良好的热稳定性（T d  = 258°C），低灵敏度和优异的爆轰速度（8719 m s -1）。和压力（32.9 GPa），表明它有潜力用作高能量密度材料。
• 농축된 황산 매질 중의 ＯＴＡ 용액을 수득하는 방법, 상기 용액 및 ＯＮＴＡ의 제조 방법
  申请人：SAFRAN CERAMICS 사프란 세라믹스(520120531618)

  公开号：KR20160028405A

  公开（公告）日：2016-03-11

  본 발명은 농축된 황산 중에 1,2,4-트리아졸-5-온(3)(OTA)을 함유하는 용액을 수득하는 방법(상기 방법은 OTA(3)의 전구체로서 3-아미노-1,2,4-트리아졸(1)(ATA)을 사용한다), 상기 용액 및 상기 용액으로부터 3-니트로-1,2,4-트리아졸-5-온(4)(ONTA)의 제조 방법에 관한 것이다.

  该专利涉及一种制备含有浓缩硫酸中1,2,4-三唑-5-醌(3)(OTA)的溶液的方法(其中该方法使用3-氨基-1,2,4-三唑(1)(ATA)作为OTA(3)的前体)，以及涉及该溶液和从该溶液制备3-硝基-1,2,4-三唑-5-醌(4)(ONTA)的方法。

表征谱图