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.
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').
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.
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.
/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/
/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.
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.
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.
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.
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
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 energeticsaltsbased 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
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）。
A new family of nitrogen-rich fused-triazole energeticsaltsbased 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.
