3,5-二硝基吡啶-4-羧酸 | 191017-95-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3,5-二硝基吡啶-4-羧酸
• 中文别名: 3,5-二硝基异烟酸
• 英文名称: 3,5-dinitropyridine-4-carboxylic Acid
• CAS: 191017-95-5
• 化学式: C₆H₃N₃O₆
• 分子量: 213.106
• InChiKey: WDAWZQCOUPDUDY-UHFFFAOYSA-N

物化性质

• 沸点：
  496.5±45.0 °C(Predicted)
• 密度：
  1.792±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  3,3-dinitroazetidine hydrochloride 以 水 为溶剂， 生成 3,5-二硝基吡啶 、 3,3-dinitro-propan-1-ol 、 1,3,3-trinitroazetidine 、 1-Formyl-3,3-dinitroazetidine 、 1-nitroso-3,3-dinitroazetidine 、 3,5-二硝基吡啶-4-羧酸
  参考文献：
  名称：

  Thermal Decomposition Pathways of 1,3,3-Trinitroazetidine (TNAZ), Related 3,3-Dinitroazetidium Salts, and ¹⁵N, ¹³C, and ²H Isotopomers

  摘要：

  The thermal decomposition of 1,3,3-trinitroazetidine (TNAZ) and related 3,3-dinitroazetidium (DNAZ(+)) salts was examined neat and in solution. TNAZ kinetics were found (160-250 degrees C) to be first-order and nearly identical neat and in benzene, with an activation energy of 46.6 kcal/mol (195 kJ/mol). The DNAZ(+) salts were less thermally stable than TNAZ, and neat did not decompose in a first-order fashion. However, in aqueous solution the DNAZ(+) salts did decompose following first-order kinetics; their rates were similar with minor differences apparently related to the strength of the anion as a conjugate base. Like simple nitramines such as dimethylnitramine, TNAZ tended to form N2O rather than N-2, but unlike other nitramines it formed about as much NO as N2O. TNAZ isotopomers labeled with C-13 and with N-15 were prepared and used to identify the origin of the decomposition gases and the identity of the condensed-phase products. Early in the decomposition of TNAZ, most of the NO came from the nitro group attached to the azetidium ring nitrogen. Most of the N2O was the result of the nitro groups interacting with each other, while the majority of the N-2 contained one nitrogen from the ring. Many condensed products have been identified, but five stand out because they are formed in the thermolysis of TNAZ and the three DNAZ(+) salts [NO3-, Cl-, N(NO2)(2)(-)]. These are 3,5-dinitropyridine (M, always a minor product), 1-formyl-3,3-dinitroazetidine (L), 1,3-dinitroazetidine (K), 1-nitroso-3,3-dinitroazetidine (E), and 1-nitroso-3-nitroazetidine (G); the identity of the first four has been confirmed by use of authentic samples. Of these five, the last four have been shown to interconvert with TNAZ and each other under the conditions of these experiments. This study confirms the presence of two competitive TNAZ decomposition pathways. Under the conditions of this study, N-NO2 homolysis is slightly favored, but products, such as K, resulting from C-NO2 scission, are also well represented.

  DOI：

  10.1021/jp9700950

文献信息

• Thermal Decomposition Pathways of 1,3,3-Trinitroazetidine (TNAZ), Related 3,3-Dinitroazetidium Salts, and ¹⁵N,¹³C, and ²H Isotopomers
  作者：Jimmie Oxley、James Smith、Weiyi Zheng、Evan Rogers、Michael Coburn

  DOI：10.1021/jp9700950

  日期：1997.6.1

  The thermal decomposition of 1,3,3-trinitroazetidine (TNAZ) and related 3,3-dinitroazetidium (DNAZ(+)) salts was examined neat and in solution. TNAZ kinetics were found (160-250 degrees C) to be first-order and nearly identical neat and in benzene, with an activation energy of 46.6 kcal/mol (195 kJ/mol). The DNAZ(+) salts were less thermally stable than TNAZ, and neat did not decompose in a first-order fashion. However, in aqueous solution the DNAZ(+) salts did decompose following first-order kinetics; their rates were similar with minor differences apparently related to the strength of the anion as a conjugate base. Like simple nitramines such as dimethylnitramine, TNAZ tended to form N2O rather than N-2, but unlike other nitramines it formed about as much NO as N2O. TNAZ isotopomers labeled with C-13 and with N-15 were prepared and used to identify the origin of the decomposition gases and the identity of the condensed-phase products. Early in the decomposition of TNAZ, most of the NO came from the nitro group attached to the azetidium ring nitrogen. Most of the N2O was the result of the nitro groups interacting with each other, while the majority of the N-2 contained one nitrogen from the ring. Many condensed products have been identified, but five stand out because they are formed in the thermolysis of TNAZ and the three DNAZ(+) salts [NO3-, Cl-, N(NO2)(2)(-)]. These are 3,5-dinitropyridine (M, always a minor product), 1-formyl-3,3-dinitroazetidine (L), 1,3-dinitroazetidine (K), 1-nitroso-3,3-dinitroazetidine (E), and 1-nitroso-3-nitroazetidine (G); the identity of the first four has been confirmed by use of authentic samples. Of these five, the last four have been shown to interconvert with TNAZ and each other under the conditions of these experiments. This study confirms the presence of two competitive TNAZ decomposition pathways. Under the conditions of this study, N-NO2 homolysis is slightly favored, but products, such as K, resulting from C-NO2 scission, are also well represented.