1,3,5-triazido-2,4,6-trichlorobenzene | 1443758-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-triazido-2,4,6-trichlorobenzene
• 英文别名: 1,3,5-Triazido-2,4,6-trichlorobenzene
• CAS: 1443758-94-8
• 化学式: C₆Cl₃N₉
• 分子量: 304.485
• InChiKey: ZAUFPINHCVNKCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,5-triazido-2,4,6-trichlorobenzene 生成 1,3,5-trinitreno-2,4,6-trichlorobenzene
  参考文献：
  名称：

  基质分离的七重奏 1,3,5-trinitreno-2,4,6-trichlorobenzo 的磁各向异性参数

  摘要：

  记录了 1,3,5-三叠氮基-2,4,6-三氯苯在 15 K 的固态氩中光解产生的高对称性 1,3,5-trinitreno-2,4,6-三氯苯的 ESR 谱. 计算机模拟显示光谱对应于具有精细结构参数 DS = -0.0957±0.0006 cm-1 和 ES = 0±0.0004 cm-1 的 septet 自旋状态。这些磁各向异性参数 DS 和 ES 的值与 UDFT 计算结果非常吻合。具有 D3h 对称性的 septet 分子的自旋-自旋 (DSS) 和自旋-轨道 (DSO) 耦合参数为负值，相互增强了这些分子的磁各向异性。由于分子中存在三个氯原子，自旋轨道耦合对 1,3,5-trinitreno-2,4,6-trichlorobenzo 的磁各向异性的贡献高于 11%。

  DOI：

  10.1007/s11172-012-0315-z
• 作为产物：
  描述：

  1,3,5-三氯-2,4,6-三氟苯 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以98%的产率得到1,3,5-triazido-2,4,6-trichlorobenzene
  参考文献：
  名称：

  Triazidation of 2,4,6-trifluorobenzenes

  摘要：

  1,3,5-Trichloro-2,4,6-trifluorobenzene and 1-bromo-3,5-dichloro-2,4,6-trifluorobenzene undergo selective defluorination on heating in dimethylsulfoxide with sodium azide to form 1,3,5-triazido-2,4,6-trichlorobenzene and 1,3,5-triazido-2-bromo-4,6-dichlorobenzene in high yields. The azidation of 1,3,5-tribromo-2,4,6-trifluorobenzene under similar reaction conditions leads to the mixture of 1,3-diazido2,4,6-tribromo-5-fluorobenzne and 1,3,5-triazido-2,4,6-tribromobenzene in the 1:2 ratio, respectively. 1,3,5-Triazido-2,4,6-tribromobenzene can be obtained as a sole product in high yield if the azidation of 1,3,5-tribromo-2,4,6-trifluorobenzene with sodium azide is carried out in aqueous acetone. The triazides obtained are the first readily available 1,3,5-triazidobenzenes that may find a wide practical use as new photoactive cross-linking reagents for polymer chemistry and as starting compounds in organic synthesis and photochemical preparation of new organic magnetic materials. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.07.009

文献信息

• Magnetic anisotropy parameters of matrix-isolated septet 1,3,5-trinitreno-2,4,6-trichlorobenzene
  作者：E. Ya. Misochko、A. V. Akimov、A. A. Mazitov、D. V. Korchagin、S. V. Chapyshev

  DOI：10.1007/s11172-012-0315-z

  日期：2012.12

  anisotropy of these molecules. The contribution of the spin-orbit coupling to the magnetic anisotropy of 1,3,5-trinitreno-2,4,6-trichlorobenzene is higher than 11% due to the presence of three chlorine atoms in the molecule. This suggests the possibility of further strengthening the magnetic properties of septet 1,3,5-trinitrenobenzenes by introducing bromine and iodine atoms into positions 2, 4, and 6

  记录了 1,3,5-三叠氮基-2,4,6-三氯苯在 15 K 的固态氩中光解产生的高对称性 1,3,5-trinitreno-2,4,6-三氯苯的 ESR 谱. 计算机模拟显示光谱对应于具有精细结构参数 DS = -0.0957±0.0006 cm-1 和 ES = 0±0.0004 cm-1 的 septet 自旋状态。这些磁各向异性参数 DS 和 ES 的值与 UDFT 计算结果非常吻合。具有 D3h 对称性的 septet 分子的自旋-自旋 (DSS) 和自旋-轨道 (DSO) 耦合参数为负值，相互增强了这些分子的磁各向异性。由于分子中存在三个氯原子，自旋轨道耦合对 1,3,5-trinitreno-2,4,6-trichlorobenzo 的磁各向异性的贡献高于 11%。
• Triazidation of 2,4,6-trifluorobenzenes
  作者：Sergei V. Chapyshev、Alexander V. Chernyak

  DOI：10.1016/j.jfluchem.2013.07.009

  日期：2013.12

  1,3,5-Trichloro-2,4,6-trifluorobenzene and 1-bromo-3,5-dichloro-2,4,6-trifluorobenzene undergo selective defluorination on heating in dimethylsulfoxide with sodium azide to form 1,3,5-triazido-2,4,6-trichlorobenzene and 1,3,5-triazido-2-bromo-4,6-dichlorobenzene in high yields. The azidation of 1,3,5-tribromo-2,4,6-trifluorobenzene under similar reaction conditions leads to the mixture of 1,3-diazido2,4,6-tribromo-5-fluorobenzne and 1,3,5-triazido-2,4,6-tribromobenzene in the 1:2 ratio, respectively. 1,3,5-Triazido-2,4,6-tribromobenzene can be obtained as a sole product in high yield if the azidation of 1,3,5-tribromo-2,4,6-trifluorobenzene with sodium azide is carried out in aqueous acetone. The triazides obtained are the first readily available 1,3,5-triazidobenzenes that may find a wide practical use as new photoactive cross-linking reagents for polymer chemistry and as starting compounds in organic synthesis and photochemical preparation of new organic magnetic materials. (C) 2013 Elsevier B.V. All rights reserved.
• Persistent Organic High‐Spin Trinitrenes
  作者：Enrique Mendez‐Vega、Joel Mieres‐Perez、Sergei V. Chapyshev、Wolfram Sander

  DOI：10.1002/anie.201904556

  日期：2019.9.9

  ground state trinitrenes 1,3,5-trichloro-2,4,6-trinitrenobenzene and 1,3,5-tribromo-2,4,6-trinitrenobenzene were isolated in inert (Ar, Ne, and Xe) as well as reactive matrices (H2 , O2 , and H2 O) at cryogenic temperatures. These trinitrenes were obtained in high yields by UV photolysis of the corresponding triazides and characterized by IR and UV/Vis spectroscopy. The trinitrenes, despite bearing

  同样在惰性气体（Ar，Ne和Xe）中也分离出了七肽基态的三硝基苯二甲腈1,3,5-三氯-2,4,6-三硝基苯酚和1,3,5-三溴-2,4,6-三硝基苯酚作为低温下的反应性基质（H2，O2和H2 O）。通过对相应的三叠氮化物进行紫外线光解，可以高收率获得这些三硝基苯，并通过红外光谱和紫外/可见光谱进行表征。尽管含有六个不成对的电子，但三硝基苯对分子中的氧和氢极不反应，并在高达160 K的水冰中持续存在，在那里水基质开始升华。