7-bromobenzo-1,2,3,4-tetrazine 1,3-dioxide | 478189-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 7-bromobenzo-1,2,3,4-tetrazine 1,3-dioxide
• 英文别名: 6-Bromo-2,4-dioxido-1,2,3,4-benzotetrazine-2,4-diium
• CAS: 478189-80-9
• 化学式: C₆H₃BrN₄O₂
• 分子量: 243.019
• InChiKey: LWIAVFWGEUIUQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-bromobenzo-1,2,3,4-tetrazine 1,3-dioxide 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以53%的产率得到7-azidobenzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  摘要：

  Nucleophilic substitution in nitro- and bromobenzo-1,2,3,4-tetrazine 1,3-dioxides (BTDOs) was studied. In most cases, the bromo and nitro groups are replaced by methylamino, dimethylamino, azido, and methoxy groups without opening of the tetrazine ring. It was illustrated with the reactions of dibromo-BTDOs with sodium methoxide that the reactivity of positions 5 to 8 in their benzene ring as regards nucleophilic substitution changes in the following order: 6 > 8 > 7 > 5. The structures of the BTDOs obtained were confirmed by H-1, C-13, and N-14 NMR data.

  DOI：

  10.1023/a:1021396317258
• 作为产物：
  描述：

  4-bromo-2-(tert-butyl-NNO-azoxy)phenyldiazonium tetrafluoroborate 在 过氧化氢苯甲酰 、 sodium acetate 作用下， 以 乙腈 为溶剂， 生成 7-bromobenzo-1,2,3,4-tetrazine 1,3-dioxide
  参考文献：
  名称：

  Benzo-1,2,3,4-tetrazine 1,3-Dioxides: Synthesis and NMR Study

  摘要：

  DOI：

  10.1002/1099-0690(200207)2002:14<2342::aid-ejoc2342>3.0.co;2-h

文献信息

• ——
  作者：O. Yu. Smirnov、A. M. Churakov、Yu. A. Strelenko、S. L. Ioffe、V. A. Tartakovsky

  DOI：10.1023/a:1021344300420

  日期：——

  Benzo-1,2,3,4-tetrazine 1,3-dioxide (BTDO) and its derivatives were nitrated with HNO3/H2SO4 or HNO3/oleum and brominated with dibromoisocyanuric acid in CF3CO2H/H2SO4 (5 : 1) or H2SO4. The reactivity of positions in the benzene ring of this heterocyclic system as regards electrophilic substitution was found to change in the following order: 5 approximate to 7 > 8 > 6. Mono- and dinitro-BTDOs and mono- and polybromo-BTDOs were synthesized. Their structures were confirmed by H-1, C-13, and N-14 NMR spectra.