6,6′-dibromo-3,3′-bis(dimethylamino)-5,5′-bi-1,2,4-triazine | 824955-20-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6,6′-dibromo-3,3′-bis(dimethylamino)-5,5′-bi-1,2,4-triazine
• 英文别名: 6,6'-bisbromo-3,3'-bis(N,N-dimethylamino)-5,5'-bi-1,2,4-triazine；6-bromo-5-[6-bromo-3-(dimethylamino)-1,2,4-triazin-5-yl]-N,N-dimethyl-1,2,4-triazin-3-amine
• CAS: 824955-20-6
• 化学式: C₁₀H₁₂Br₂N₈
• 分子量: 404.067
• InChiKey: FTJPGBUYGVRYCA-UHFFFAOYSA-N

物化性质

• 沸点：
  523.6±60.0 °C(Predicted)
• 密度：
  1.816±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,6′-dibromo-3,3′-bis(dimethylamino)-5,5′-bi-1,2,4-triazine 、 2-(三丁基锡烷基)呋喃 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以63%的产率得到3,3'-bis(N,N-dimethylamino)-6,6'-bis(furan-2-yl)-5,5'-bi-1,2,4-triazine
  参考文献：
  名称：

  Structural characterization of 6,6′-bis(substituted)-5,5′-bi-1,2,4-triazines as potential N-heterocyclic ligands for the extraction of nuclear waste

  摘要：

  Novel disubstituted 5,5'-bi-1,2,4-triazines bearing pyridine (1), furan (2) and thiophene (3) rings at 6 and 6'-positions of the parent bitriazine were prepared as potential extractants of nuclear waste. The compounds were easily obtained by Stille coupling starting from 6,6'-bisbromo-3,3'-bis(N,N-dimethylamine)-5,5'-bi-1,2,4-triazine and the corresponding tin reagents. The molecular and crystal structures of the ligands 1-3 were determined by the X-ray analysis. The X-ray investigations show different conformations of the molecules described as gauche-gauche-gauche for 1 and gauche-cis-cis for 2 and 3. Each of the molecules resides on a twofold axis that passes through the middle of the central C5-05' bond. The molecular packing in 1 is influenced by the pi center dot center dot center dot pi and weak C-H center dot center dot center dot pi interactions. The crystal structures of 2 and 3 are governed by a combination of a weak C-H center dot center dot center dot N hydrogen bonds and C-H center dot center dot center dot pi interactions. Theoretical calculations using semi-empirical AM1 and DET/B3LYP/6-311++G(d,p) ab initio methods were carried out to find correlation between conformational and electronic parameters of the molecules and their preferences to metal ions complexations. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.06.023

文献信息

• A convenient synthesis of 5,5′-bi-1,2,4-triazines via direct S-arylation and its application in the synthesis of 2,2′-bipyridines
  作者：Justyna Ławecka、Ewa Olender、Zbigniew Karczmarzyk、Waldemar Wysocki、Danuta Branowska、Zofia Urbańczyk-Lipkowska、Przemysław Kalicki

  DOI：10.1515/hc-2013-0214

  日期：2014.2.1

  5′-bi-1,2,4-triazine with benzenethiolate or 2-pyridinethiolate anion afforded the corresponding symmetrical disulfide of 5,5′-bi-1,2,4-triazine in high yields. These products were transformed into 6,6′-bis(phenylthio)-2,2′-bipyridines and 6,6′-bis(2-pyridylthio)-2,2′-bipyridines by using Diels-Alder reactions. All compounds were fully characterized by spectroscopic methods and the X-ray diffraction

  摘要 3,3'-dichloro-5,5'-bi-1,2,4-triazine 中氯化物与苯硫醇或 2-pyridinethiolate 阴离子的亲核置换得到相应的对称二硫化物 5,5'-bi-1,2 ,4-三嗪收率高。通过使用Diels-Alder反应将这些产物转化为6,6'-双(苯硫基)-2,2'-联吡啶和6,6'-双(2-吡啶硫基)-2,2'-联吡啶。所有化合物都通过光谱方法和 X 射线衍射分析进行了充分表征。
• Structural characterization of 6,6′-bis(substituted)-5,5′-bi-1,2,4-triazines as potential N-heterocyclic ligands for the extraction of nuclear waste
  作者：Danuta Branowska、Zbigniew Karczmarzyk、Andrzej Rykowski、Waldemar Wysocki、Ewa Olender、Zofia Urbańczyk-Lipkowska、Przemysław Kalicki

  DOI：10.1016/j.molstruc.2010.06.023

  日期：2010.8

  Novel disubstituted 5,5'-bi-1,2,4-triazines bearing pyridine (1), furan (2) and thiophene (3) rings at 6 and 6'-positions of the parent bitriazine were prepared as potential extractants of nuclear waste. The compounds were easily obtained by Stille coupling starting from 6,6'-bisbromo-3,3'-bis(N,N-dimethylamine)-5,5'-bi-1,2,4-triazine and the corresponding tin reagents. The molecular and crystal structures of the ligands 1-3 were determined by the X-ray analysis. The X-ray investigations show different conformations of the molecules described as gauche-gauche-gauche for 1 and gauche-cis-cis for 2 and 3. Each of the molecules resides on a twofold axis that passes through the middle of the central C5-05' bond. The molecular packing in 1 is influenced by the pi center dot center dot center dot pi and weak C-H center dot center dot center dot pi interactions. The crystal structures of 2 and 3 are governed by a combination of a weak C-H center dot center dot center dot N hydrogen bonds and C-H center dot center dot center dot pi interactions. Theoretical calculations using semi-empirical AM1 and DET/B3LYP/6-311++G(d,p) ab initio methods were carried out to find correlation between conformational and electronic parameters of the molecules and their preferences to metal ions complexations. (C) 2010 Elsevier B.V. All rights reserved.