6,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide | 478189-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 6,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide
• 英文别名: 6,7-dibromobenzotetrazine 1,3-dioxide；6,7-bromobenzotetrazine 1,3-dioxide；6,7-Dibromo-2,4-dioxido-1,2,3,4-benzotetrazine-2,4-diium
• CAS: 478189-81-0
• 化学式: C₆H₂Br₂N₄O₂
• 分子量: 321.915
• InChiKey: TXAYIGAJANPDQV-UHFFFAOYSA-N

物化性质

• 沸点：
  512.0±46.0 °C(Predicted)
• 密度：
  2.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 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：

  6,7-dibromobenzo-1,2,3,4-tetrazine 1,3-dioxide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以91%的产率得到6-azido-7-bromobenzotetrazine 1,3-dioxide
  参考文献：
  名称：

  Benzo-1,2,3,4-tetrazine 1,3-dioxides annulated with tetraazapentalene systems

  摘要：

  热解 7-叠氮-6-(2H-1,2,3-三唑-2-基)-1,2,3,4-苯并四嗪 1,3-二氧化物和 7-叠氮-6-(1H-1,2,3-三唑-1-基)-1,2,3,4-苯并四嗪 1,3-二氧化物可产生新的杂环系统：6,10-dehydro-6H,10H-[1,2,3]triazolo[1′,2′:2,3][1,2,3]triazolo[4,5-g]-[1,2,3,4]benzotetrazine 2,4-dioxide and 6,8-dehydro-6H,8H-[1,2,3]triazolo[1′,2′:1,2][1,2,3]-三唑并[4,5-g][1,2,3,4]苯并四嗪 2,4-二氧化物的热稳定性和光谱特性进行了研究。

  DOI：

  10.1007/s11172-008-0296-0
• 作为产物：
  描述：

  4,5-dibromo-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 6,7-dibromobenzo-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

• An unusual cascade of S N reactions of benzotetrazine 1,3-dioxide derivatives
  作者：A. Yu. Tyurin、O. Yu. Smirnov、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/s11172-010-0017-3

  日期：2009.2

  give 5-azido-6-(1,2,3-triazol-2-yl)benzotetrazine 1,3-dioxide, with 8-azido-7-nitrobenzotetrazine 1,3-dioxide to give 7-azido-8-(1,2,3-triazol-2-yl)benzotetrazine 1,3-dioxide and 7-azido-8-(1,2,3-triazol-1-yl)benzotetrazine 1,3-dioxide, and with 7-bromo-6-(phenylthio)benzotetrazine 1,3-dioxide to give 7-phenylthio-6-(1,2,3-triazol-2-yl)benzotetrazine 1,3-dioxide.

  在苯环中包含两个相邻的离核剂 X 和 Y 的苯并 1,2,3,4-四嗪 1,3-二氧化物系列中发现了不寻常的 SNAr 级联反应。首先，1,2,3-三唑阴离子从更具反应性的位点置换阴离子Xs-。然后亲核试剂 Xs- 取代相邻的基团 Y。例如，1,2,3-三唑与 6-azido-5-nitrobenzotetrazine 1,3-dioxide 反应得到 5-azido-6-(1,2, 3-triazol-2-yl)benzotetrazine 1,3-dioxide, with 8-azido-7-nitrobenzotetrazine 1,3-dioxide 得到 7-azido-8-(1,2,3-triazol-2-yl)benzotetrazine 1,3-二氧化物和 7-叠氮基-8-(1,2,3-三唑-1-基)苯并四嗪 1,3-二氧化物，并与 7-溴-6-(苯硫基)苯四嗪 1,3-二氧化物得到
• Annulated benzotetrazine 1,3-dioxides 1. [1,2,5]Oxadiazolo[3,4-f][1,2,3,4]benzotetrazine 2,4,7-and 2,4,9-trioxides
  作者：O. Yu. Smirnov、A. Yu. Tyurin、A. M. Churakov、Yu. A. Strelenko、V. A. Tartakovsky

  DOI：10.1007/s11172-006-0226-y

  日期：2006.1

  Thermolysis of 6-azido-5-nitro-7-R-benzotetrazine 1,3-dioxides (R = H and Br) gave benzotetrazine 1,3-dioxides annulated with the furoxan ring at the C(5)-C(6) bond. According to the NMR data, these compounds at 297 K are equilibrium mixtures of two isomers with different positions of the N-oxide oxygen atom in the furoxan ring. Full assignment of signals in the 13C NMR spectra of the compounds obtained was accomplished.

  6-azido-5-nitro-7-R-benzotetrazine 1,3-dioxides（R = H 和 Br）热分解后得到了在 C(5)-C(6) 键处与呋喃环成环状的 benzotetrazine 1,3-dioxides 。根据核磁共振数据，这些化合物在 297 K 时是呋喃环中 N-氧化氧原子位置不同的两种异构体的平衡混合物。所获化合物的 13C NMR 光谱中的信号已完全确定。
• ——
  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.
• ——
  作者：O. Yu. Smirnov、A. M. Churakov、A. Yu. Tyurin、Yu. A. Strelenko、S. L. Ioffe、V. A. Tartakovsky

  DOI：10.1023/a:1021396317258

  日期：——

  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.
• Benzo-1,2,3,4-tetrazine 1,3-Dioxides: Synthesis and NMR Study
  作者：Aleksandr M. Churakov、Oleg Yu. Smirnov、Sema L. Ioffe、Yuri A. Strelenko、Vladimir A. Tartakovsky

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

  日期：2002.7