1,2,3-triazolo<1,2-a>benzotriazole | 10560-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1,2,3-triazolo<1,2-a>benzotriazole
• 英文别名: triazolo(1,2-a)benzotriazole；1H-benzo[d][1,2,3]triazolo[1,2-a][1,2,3]triazolium betaine；2,3-Benzo-1,3a,4,6a,tetraaza-pentalen；2,3-Benzo-1,3a,6,6a,tetraaza-pentalen；Benzo-1,3a,6,6a-tetraazapentalen；1,2,3-triazolo[1,2-a]benzotriazole；2,7-Diaza-6-azonia-5-azanidatricyclo[6.4.0.02,6]dodeca-1(12),3,6,8,10-pentaene
• CAS: 10560-67-5
• 化学式: C₈H₆N₄
• 分子量: 158.162
• InChiKey: RUVMAUACUPMMCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3-triazolo<1,2-a>benzotriazole 在 sodium azide 、 18-冠醚-6 、 硫酸 、 硝酸 作用下， 以 乙腈 为溶剂， 反应 18.33h， 生成 4,6-dinitro-1H-benzotriazole
  参考文献：
  名称：

  Chemistry of Tetraazapentalenes

  摘要：

  2,4,8, 10-Tetranitrobenzotriazolo[2, 1-alpha]benzotriazole (TACOT), although thermally very stable and insensitive as an explosive, is susceptible to attack by nucleophiles. Reaction with azide ion results in displacement of nitro groups at the 4,10-positions, treatment with methoxide ion effects displacement of the hydrogen atom at the 1-position and scission of the remote triazole ring, while "vicarious nucleophilic amination" displaces all the aromatic hydrogens. 3,5,7-Trinitro-1,3,3-triazolo[2, 1-alpha]benzotriazole and 3,5,7-trinitro-1,2,3-triazolo[1,2-alpha]benzotriazole are prepared readily by nitration of the parent triazolobenzotriazoles. However they are thermally less stable than TACOT and more sensitive to initiation by impact. Furthermore, attempted further nitration and reaction with nucleophiles such as azide and methoxide ions both effect scission of the triazole ring to leave 4,6-dinitrobenzotriazole.

  DOI：

  10.1021/jo972252x
• 作为产物：
  描述：

  1-(2-nitrophenyl)-1H-1,2,3-triazole 在 三甲氧基磷 作用下， 生成 1,2,3-triazolo<1,2-a>benzotriazole
  参考文献：
  名称：

  Chemistry of Tetraazapentalenes

  摘要：

  2,4,8, 10-Tetranitrobenzotriazolo[2, 1-alpha]benzotriazole (TACOT), although thermally very stable and insensitive as an explosive, is susceptible to attack by nucleophiles. Reaction with azide ion results in displacement of nitro groups at the 4,10-positions, treatment with methoxide ion effects displacement of the hydrogen atom at the 1-position and scission of the remote triazole ring, while "vicarious nucleophilic amination" displaces all the aromatic hydrogens. 3,5,7-Trinitro-1,3,3-triazolo[2, 1-alpha]benzotriazole and 3,5,7-trinitro-1,2,3-triazolo[1,2-alpha]benzotriazole are prepared readily by nitration of the parent triazolobenzotriazoles. However they are thermally less stable than TACOT and more sensitive to initiation by impact. Furthermore, attempted further nitration and reaction with nucleophiles such as azide and methoxide ions both effect scission of the triazole ring to leave 4,6-dinitrobenzotriazole.

  DOI：

  10.1021/jo972252x

文献信息

• PYRIDAZINO[2,3-<i>b</i>]BENZO-1,2,4-TRIAZINE. A NEW HETEROCYCLE AND A NEW STABLE FREE RADICAL
  作者：Angelo Albini、Gian Franco Bettinetti、Giovanna Minoli、Teresa Fulle Soldi

  DOI：10.1246/cl.1984.1197

  日期：1984.7.5

  The preparation of the new stable free radical 2,a derivative of the previously unreported pyridazino[1,2-b]benzo-1,2,4-triazine, and some of its chemical properties are described.

  描述了新的稳定自由基 2 的制备，它是先前未报道的哒嗪并 [1,2-b] 苯并-1,2,4-三嗪的衍生物，并描述了其一些化学性质。
• Photooxidation of some triaza- and tetraazabenzopentalenes
  作者：Angelo Albini、Gian Franco Bettinetti、Giovanna Minoli

  DOI：10.1021/jo00155a030

  日期：1983.4
• Heteropentalenes. The thermal addition of pyrazolo- and triazolobenzotriazoles to dimethyl acetylenedicarboxylate
  作者：Angelo Albini、Gianfranco Bettinetti、Giovanna Minoli

  DOI：10.1021/jo00189a003

  日期：1984.7
• ALBINI, A.;BETTINETTI, G. F.;MINOLI, G.;FULLE, SOLDI, T., CHEM. LETT., 1984, N 7, 1197-1198
  作者：ALBINI, A.、BETTINETTI, G. F.、MINOLI, G.、FULLE, SOLDI, T.

  DOI：——

  日期：——
• ALBINI, A.;BETTINETTI, G.;MINOLI, G., J. OGR. CHEM., 1984, 49, N 15, 2670-2676
  作者：ALBINI, A.、BETTINETTI, G.、MINOLI, G.

  DOI：——

  日期：——