4-(1H-1,2,3-benzotriazol-1-yl)-5-nitrophthalonitrile | 274924-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1H-1,2,3-benzotriazol-1-yl)-5-nitrophthalonitrile
• 英文别名: 4-(1-benzotriazol-1-yl)-5-nitrophthalodinitrile；4-(1H-benzotriazol-1-yl)-5-nitrophthalonitrile；4-(1-benzotriazolyl)-5-nitrophthalodinitrile；4-(1-benzotriazolyl)-5-nitrophthalonitrile；4-(benzotriazol-1-yl)-5-nitrobenzene-1,2-dicarbonitrile
• CAS: 274924-71-9
• 化学式: C₁₄H₆N₆O₂
• 分子量: 290.241
• InChiKey: NYNSBVXDCWPVAY-UHFFFAOYSA-N

物化性质

• 熔点：
  234-236 °C
• 沸点：
  580.8±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(1H-1,2,3-benzotriazol-1-yl)-5-nitrophthalonitrile 在 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以90%的产率得到4-(1-benzotriazolyl)-5-hydroxyphthalonitrile
  参考文献：
  名称：

  4-(1-Benzotriazolyl)-5-nitrophthalonitrile as a highly active substrate in aromatic nucleophilic substitution reactions

  摘要：

  The title compound was synthesised, and its derivatives were prepared in high yields using the selective substitution of O-, S- and N-nucleophiles for the nitro group; an activating effect of the benzotriazolyl moiety on the above reactions was found.

  DOI：

  10.1070/mc2002v012n02abeh001538
• 作为产物：
  描述：

  4-溴-5-硝基-1,2-苯二甲腈 在 三乙胺 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 、 异丙醇 为溶剂， 反应 3.0h， 生成 4-(1H-1,2,3-benzotriazol-1-yl)-5-nitrophthalonitrile
  参考文献：
  名称：

  4-(1-Benzotriazolyl)-5-nitrophthalonitrile as a highly active substrate in aromatic nucleophilic substitution reactions

  摘要：

  The title compound was synthesised, and its derivatives were prepared in high yields using the selective substitution of O-, S- and N-nucleophiles for the nitro group; an activating effect of the benzotriazolyl moiety on the above reactions was found.

  DOI：

  10.1070/mc2002v012n02abeh001538

文献信息

• Nucleophilic substitution of 4-bromo-5-nitrophthalodinitrile: XIII. Synthesis and properties of 4-(1-benzotriazolyl)-5-(4-tritylphenoxy)phthalonitrile and phthalocyanines based thereon
  作者：S. A. Znoyko、A. I. Savinova、V. E. Maizlish、G. P. Shaposhnikov、I. G. Abramov

  DOI：10.1134/s1070363216060207

  日期：2016.6

  4-(1-Benzotriazolyl)-5-(4-tritylphenoxy)phthalonitrile was synthesized by nucleophilic substitution of bromine and nitro group of 4-bromo-5-nitrophthalonitrile, and on its basis the corresponding octa-substituted phthalocyanines were obtained. Spectral properties of the synthesized compounds were investigated.

  通过溴和4-溴-5-硝基邻苯二甲腈的硝基的亲核取代反应，合成了4-（1-苯并三唑基）-5-（4-三苯甲酰苯氧基）邻苯二甲腈，并在此基础上得到了相应的八取代邻苯二甲腈。研究了合成化合物的光谱性质。
• Nucleophilic substitution in 4-bromo-5-nitrophthalodinitrile: X. Synthesis of 4-(1-benzotriazolyl)-5-(1(2)-naphthyloxy)-phthalodinitriles and related phthalocyanines
  作者：S. A. Znoiko、A. S. Kambolova、V. E. Maizlish、G. P. Shaposhnikov、I. G. Abramov、S. I. Filimonov

  DOI：10.1134/s107036320908026x

  日期：2009.8

  4-(1-Benzotriazolyl)-5-[1(2)-naphthyloxy]phthalodinitriles were obtained by nucleophilic substitution of bromine and nitro group in 4-bromo-5-nitrophthalodinitrile. These compounds were used for the synthesis of the corresponding octa-substituted phthalocyanines. Spectral data of the compounds obtained were examined.

  通过亲核取代4-溴-5-硝基邻苯二甲腈中的溴和硝基，得到4-（1-苯并三唑基）-5- [1（2）-萘氧基]邻苯二腈。这些化合物用于合成相应的八取代的酞菁。检查获得的化合物的光谱数据。
• Nucleophilic substitution in 4-bromo-5-nitrophthalodinitrile: XI. Preparation, properties, and prediction of mesomorphism in mixed-substituted phthalocyanines containing aryloxy and benzotriazole fragments
  作者：S. A. Znoiko、O. B. Akopova、N. V. Bumbina、N. V. Usoltseva、V. E. Maizlish、G. P. Shaposhnikov、I. G. Abramov

  DOI：10.1134/s1070363214040185

  日期：2014.4

  Stepwise nucleophilic substitution of bromine and nitro group in 4-bromo-5-nitrophthalodinitrile has led to a series of phthalonitriles containing benzotriazole and aryloxy fragments; basing on them, the mixed-substituted phthalocyanines have been prepared. The spectral properties of products have been studied. According to simulation of columnar mesomorphism only one of the products is not capable of mesomorphism characteristic of discotic mesogens; the result has been confirmed with the experiment.
• Nucleophilic substitution in 4-bromo-5-nitrophthalodinitrile: VIII. Synthesis of 4-(benzotriazol-1-yl)-5-[4-(1-methyl-1-phenylethyl)phenoxy]phthalodinitrile and phthalocyanines on its basis
  作者：S. A. Znoiko、V. E. Maizlish、G. P. Shaposhnikov、I. G. Abramov、M. N. Voron’ko

  DOI：10.1134/s1070363207090216

  日期：2007.9

  Nucleophilic aromatic substitution of the bromine atom in 4-bromo-5-nitrophthalodinitrile by a 2-aminophenylamine residue followed by conversion of the resulting compound to 4-(1-benzothiazol-1-yl)-5-nitrophthalodinitrile and nucleophilic substitution of the nitro group by a 4-(1-methyl-1-phenylethyl)-phenoxy group gave 4-(benzotriazol-1-yl)-5-[4-(1-methyl-1-phenylethyl)phenoxy]phthalodinitrile. The latter product was reacted with certain metal acetates and chlorides to obtain the corresponding metal complexes of octasubstituted phthalocyanines. Spectral properties of the complexes were studied.
• Nucleophilic Substitution in 4-Bromo-5-nitrophthalodinitrile: XVI.1 4-(1H-Benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy/sulfanyl]- phthalonitriles and Cobalt Phthalocyanines Thereof
  作者：S. A. Znoiko、I. A. Kuz’min、T. V. Tikhomirova、N. N. Smirnov、V. E. Maizlish、A. S. Vashurin、G. P. Shaposhnikov

  DOI：10.1134/s1070363218040205

  日期：2018.4

  A method of synthesis of 4-(1H-benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy]- and -5-[(4-carboxyphenyl) sulfanyl]phthalonitriles starting with 4-bromo-5-nitrophthalonitriles was developed. The synthesized phthalonitriles were used to prepare cobalt tetra-4-(1H-benzotriazol-1-yl)-tetra-5-[(4-carboxyphenyl)oxy/sulfanyl]phthalocyanines. The spectral and catalytic properties of the resulting octasubstituted phthalocyanines were studied.