1,3,5-三亚硝基-1,3,5-六氢化三嗪 | 13980-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 中文名称: 1,3,5-三亚硝基-1,3,5-六氢化三嗪
• 中文别名: 六氢化-1,3,5-三亚硝基-1,3,5-三嗪；1,3,5-三亚硝基-1,3,5-三氮杂环己烷
• 英文名称: 1,3,5-trinitroso-1,3,5-triazinane
• 英文别名: 1,3,5-trinitroso-1,3,5-triazacyclohexane；hexahydro-1,3,5-trinitroso-1,3,5-triazine
• CAS: 13980-04-6
• 化学式: C₃H₆N₆O₃
• 分子量: 174.119
• InChiKey: HFWOSHMLDRSIDN-UHFFFAOYSA-N

物化性质

• 熔点：
  102.85°C
• 沸点：
  305.07°C (rough estimate)
• 密度：
  1.7121 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  98
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2933699090

反应信息

• 作为反应物：
  描述：

  1,3,5-三亚硝基-1,3,5-六氢化三嗪 在 双氧水 、 硝酸 作用下， 生成 黑索金
  参考文献：
  名称：

  Brockman et al., Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 469,470

  摘要：

  DOI：
• 作为产物：
  描述：

  乌洛托品 在 盐酸 、 sodium nitrite 作用下， 以20%的产率得到1,3,5-三亚硝基-1,3,5-六氢化三嗪
  参考文献：
  名称：

  Nitrosation Products of Hexamethylenetetramine

  摘要：

  Two nitrosation products of hexamethylenetetramine, namely 1,3,5-trinitrosoheuahydro-1,3,5-triazine (1) and 3,7-dinitroso-1,3,5,7-tetrazabicyclo[3.3.1]nonane (2), were synthesized, It is shown that both compounds in vitro at 37 degrees C (1 h, pH 7.4) form nitric oxide at a rate of 3.1% (1) or 1.3% (2), respectively. In rats (60 mg/kg p.o.) both compound inhibit thrombus formation in arterioles (1: 20%; 2: 16%) and venules (1: 18%; 2: 9%). Compound 2 does not influence the blood pressure in spontaneously hypertensive rats.

  DOI：

  10.1002/(sici)1521-4184(19997)332:7<255::aid-ardp255>3.0.co;2-r

文献信息

• Mechanisms of Nitramine Thermolysis
  作者：J. C. Oxley、A. B. Kooh、R. Szekeres、W. Zheng

  DOI：10.1021/j100079a019

  日期：1994.7

  The thermal decomposition of a number of nitramines was studied in dilute solution and in the melt, The nitramines included acyclic mononitramines [dimethylnitramine (DMN), diethylnitramine (DEN), dipropylnitramine (DPN), and diisopropylnitramine (DIPN)], cyclic mononitramines [N-nitropiperidine (NPIP) and N-nitropyrrolidine (NPyr)], cyclic dinitramines [N-dinitropiperazine (pDNP), 1,3-dinitro-1,3-diazacyclopentane (DNI), and 1,3-dinitro-1,3-diazacyclohexane (mDNP)], and 1,3,5-trinitro-1,3,5-triazocyclohexane (RDX), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), hexanitrohexaazaisowurtzitane (HNIW), and 1,3,3-trinitroazetidine (TNAZ). For the acyclic and cyclic mono- and dinitramines, the corresponding nitrosamines were the only or major condensed-phase product. Kinetics and activation parameters were determined for the thermolysis of dilute solutions (0.01-1.0 wt %) over the range 200-300 degrees C. The thermolyses were found to be first-order with the rate constants unaffected by the use of deuterated solvent. As the nitramines became more complex than dimethylnitramine (DMN), the rate of decomposition increased and the product distribution became more complex. As the length of the aliphatic chain increased (DMN < DEN < DPN), the rate of thermolysis increased, yet nitrosamine remained the only observed condensed-phase product. When a secondary carbon was attached to the N-nitramine (DIPN) rather than the primary (DPN), the rate of decomposition increased and a new condensed-phase product was observed. Among the cyclic nitramines, the rate of decomposition increased as the number of NNO2 groups increased (NPIP < pDNP; NPyr < DNI; mDMP < RDX). The position of the nitramine groups affected the decomposition: meta NNO2 groups (mDNP) decomposed faster than para (pDNP). Ring strain decreased stability: mDNP < DNI; HMX < RDX. In complex nitramines, the increase in decomposition rate, the appearance of new products, and the change in the relative importance of nitrosamine and of N-2 and N2O are attributed to new decomposition routes available to them. However, since complex nitramines (e.g. RDX) maintain first-order kinetics and since most have activation energies in the range of 40-50 kcal/mol, it is believed that the triggering mechanism remains N-NO2 homolysis. Intramolecular hydrogen transfer is also considered an important mode of nitramine decomposition.
• ——
  作者：G. A. Lyushnina、A. Yu. Bryukhanov、M. Turkina、K. V. Malakhov、E. L. Golod

  DOI：10.1023/a:1012443003868

  日期：——

  Potassium amidosulfate reacts with formaldehyde at pH 7-12 to afford a mixture of dipotassium 4-hydroxy-1,3-diazabutane-1,3-disulfonate hydrate and tripotassium 6-hydroxy-1,3,5-triazahexane-1,3,5-trisulfonate HO(CH2NSO3K)(n) . H2O (n = 2, 3). The reaction of the same compounds at pH 1-3 gives diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonic acid sulfate dihydrate.
• Evidence of an Elimination Mechanism in Thermal Decomposition of Hexahydro-1,3,5-trinitro-1,3,5-triazine and Related Compounds under High Pressure in Solution
  作者：Jiang Wang、Kay R. Brower、Darren L. Naud

  DOI：10.1021/jo970775z

  日期：1997.12.1

  The thermal decomposition of a number of six-membered cyclic nitramines and nitrosamines was studied under pressures up to 1.1 GPa in dilute solution (THF). The studied nitramines and nitrosamines include hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) hexahydro-5-methyl-1,3,5-trinitropyrimidine, hexahydro-1,3,5,5-tetranitropyrimidine, 1,3,3,5,5-pentanitrbpiperidine, and hexahydro-1,3,5-trinitroso-1,3,5-triazine (TRDX). In all cases negative activation volumes have been found, indicating that thermolysis is not a homolytic process. On the basis of negative activation volumes, detection of aromatic products, low decomposition temperature (low E-a), and order of thermal stability, we propose that these cyclic nitramines and nitrosamines are thermally decomposed through the elimination of HNO2 or HNO under-high pressure. By summarizing our current and previous work, we find that the decomposition pathway of nitrosamines and nitrosamines is dependent not only on the reaction conditions but also on structural features.
• Thermal decomposition of energetic materials. 4. Deuterium isotope effects and isotopic scrambling (H/D, 13C/18O, 14N/15N) in condensed-phase decomposition of 1,3,5-trinitrohexahydro-s-triazine (RDX)
  作者：Richard Behrens、Suryanarayana Bulusu

  DOI：10.1021/j100201a037

  日期：1992.10

  The inter- vs intramolecular origin of the products formed in the thermal decomposition of 1,3,5-trinitrohexahydro-s-triazine (RDX) has been traced by isotopic crossover experiments using mixtures of differently labeled analogues of RDX. The isotopic analogues of RDX used in the experiments include H-2, C-13, N-15, and O-18. The fraction of isotopic scrambling and the extent of the deuterium kinetic isotope effect (DKIE) are reported for the different thermal decomposition products. Isotopic scrambling is not observed for the N-N bond in N2O and only in small amounts (7%) in the C-H bonds in CH2O, consistent with a mechanism of their formation through methylene nitramine precursors. A product, oxy-s-triazine (OST, C3H3N3O) does not undergo isotopic scrambling in H/D, N-14/N-15, or C-13/O-18 experiments, and its rate of formation exhibits a DKIE of 1.5. These results are consistent with the formation of OST via unimolecular decomposition of RDX. Another product, 1-nitroso-3,5-dinitrohexahydro-s-triazine (ONDNTA, C3H6N6O5) is found to be formed with complete scrambling of the N-NO bond, suggesting an N-N bond cleavage and a radical recombination process in its formation. One of the hydrogen containing products, H2O, exhibits a DKIE of 1.5 +/- 0.1. In contrast, CH2O and ONDNTA have DKIEs of 1.05 +/- 0.1 and 1.05 +/- 0.2, respectively, indicating that hydrogen transfer is not involved in the rate-limiting step of the reaction pathway leading to the formation of these products.
• Knudsen, Chemische Berichte, 1914, vol. 47, p. 2699
  作者：Knudsen

  DOI：——

  日期：——

表征谱图