4,5-di(bromomethyl)-1,2-dicyanobenzene | 42200-14-6

• 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: 4,5-di(bromomethyl)-1,2-dicyanobenzene
• 英文别名: 4,5-di(bromomethyl)phthalonitrile；4,5-bis(bromomethyl)phthalonitrile；4,5-Bis(bromomethyl)benzene-1,2-dicarbonitrile；4,5-bis(bromomethyl)benzene-1,2-dicarbonitrile
• CAS: 42200-14-6
• 化学式: C₁₀H₆Br₂N₂
• 分子量: 313.979
• InChiKey: KNBXCNHLPDPZBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-di(bromomethyl)-1,2-dicyanobenzene 在 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2a,10b-Bis-(4-heptyl-phenyl)-1,4-dioxo-1,2,2a,3,4,5,10,10b-octahydro-2,3,4a,10a-tetraaza-benzo[g]cyclopenta[cd]azulene-7,8-dicarbonitrile
  参考文献：
  名称：

  A self-assembled phthalocyanine dimer

  摘要：

  The synthesis of phthalocyanines la and Ib appended with four glycoluril modules is presented. H-1 NMR spectroscopy showed that la and Ib self-assemble by means of hydrogen bonding to form discrete dimers. Capsule formation is solvent dependent where the dimeric assembly is most pronounced in aromatic solvents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00501-3
• 作为产物：
  描述：

  4,5-二甲基-1,2-苯二甲腈 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 1.5h， 以71%的产率得到4,5-di(bromomethyl)-1,2-dicyanobenzene
  参考文献：
  名称：

  Synthesis, spectroscopy and electrochemistry of phthalocyanine derivatives functionalised with four and eight peripheral tetrathiafulvalene units

  摘要：

  无金属酞菁衍生物2和14分别带有八个和四个外围的四硫富瓦烯（TTF）单元，已被合成，并研究了它们的溶液电化学和光学光谱。这些化合物表现出源自TTF和酞菁基团的氧化还原特性。溶液中的1H核磁共振和紫外-可见光谱研究显示，聚集强烈依赖于溶剂。观察到TTF单元对酞菁核心的荧光淬灭效应。在此工作中合成的4,5-双(己硫基)-4',5'-双(羟甲基)-TTF 11的X射线晶体结构已被测定。11的羟基参与了分子间（及堆叠间）的氢键。报告了关于酞菁衍生物2和14的计算机模拟研究。

  DOI：

  10.1039/a701703k

文献信息

• Synthesis of water-soluble phthalocyanines bearing four or eight d-galactose units
  作者：Ana R.M. Soares、João P.C. Tomé、Maria G.P.M.S. Neves、Augusto C. Tomé、José A.S. Cavaleiro、Tomás Torres

  DOI：10.1016/j.carres.2008.12.009

  日期：2009.3

  The synthesis and structural characterization of two glycophthalocyanines with four or eight unprotected D-galactose units is reported. The sugar units are linked to the macrocycle via the hydroxyl group located at C-6. The water solubility promoted by the carbohydrate moieties provides a potential application of these phthalocyanine derivatives as photosensitizers in photodynamic therapy.

  报道了具有四个或八个未保护的D-半乳糖单元的两个糖酞菁的合成和结构表征。糖单元通过位于C-6的羟基与大环连接。由碳水化合物部分促进的水溶性提供了这些酞菁衍生物作为光敏剂在光动力疗法中的潜在应用。
• New phosphorus-containing metal phthalocyanine complexes. Synthesis and spectral and electrochemical studies
  作者：A. V. Ivanov、K. V. Kabanova、M. O. Breusova、I. V. Zhukov、L. G. Tomilova、N. S. Zefirov

  DOI：10.1007/s11172-008-0218-1

  日期：2008.8

  Hitherto unknown phosphorus-containing 4,5-bis(diethoxyphosphorylmethyl)- and 4-methyl-5-diethoxyphosphorylmethylphthalonitriles were synthesized starting from o-xylene. Their tetramerization afforded free phthalocyanine ligands and their complexes with Zn, Ni, Co, and a number of rare-earth metals. The spectral and electrochemical properties of the phthalocyanines synthesized were studied.

  迄今为止尚未知的含磷化合物4,5-双(二乙氧基磷酰基甲基)和4-甲基-5-二乙氧基磷酰基甲基邻苯二腈是以邻二甲苯为起始原料合成的。它们的四聚化产物包括游离的酞菁配体及其与锌、镍、钴和若干稀土金属的配合物。对合成的酞菁的光谱和电化学性质进行了研究。
• Liquid crystalline alkylthia-substituted novel phthalocyanines: synthesis and characterization
  作者：Buket S. Erdoğan、Devrim Atilla、Ayşe G. Gürek、Vefa Ahsen

  DOI：10.1142/s1088424613501149

  日期：2014.1

  Methylene-bridged tetra- and octa-alkylthia substituted metal free- and Ni ( II ) phthalocyanines were synthesized from the corresponding phthalonitrile derivatives in the presence of the anhydrous metal salt ( NiCl ₂) or a strong organic base. The new compounds were fully characterized by elemental analyses, UV-vis, IR, NMR and mass spectra. The mesogenic properties of these materials were studied by differential scanning calorimetry, optical microscopy and X-ray diffraction investigations. X-ray diffraction patterns of the mesophase confirmed that the tetra- and the octa-substituted compounds formed hexagonal columnar mesophases (Col_h). The mesogenic properties of these compounds were compared to that of their octa alkythia substituted phthalocyanine derivatives in the literature.

  在无水金属盐（NiCl 2）或强有机碱存在下，从相应的邻苯二腈衍生物合成了亚甲基桥接的四烷基和八烷基硫代金属游离酞菁和 Ni ( II ) 酞菁。通过元素分析、紫外-可见光谱、红外光谱、核磁共振和质谱对这些新化合物进行了全面表征。通过差示扫描量热法、光学显微镜和 X 射线衍射研究了这些材料的介生特性。介相的 X 射线衍射图样证实，四代和八代化合物形成了六方柱状介相（Colh）。这些化合物的介生特性与文献中的八烷基取代酞菁衍生物进行了比较。
• 芳环并环丁烯类有机化合物、混合物、组合物及有机电子器件
  申请人：广州华睿光电材料有限公司

  公开号：CN114573587A

  公开（公告）日：2022-06-03

  本发明公开了一种芳环并环丁烯类有机化合物、混合物、组合物及有机电子器件。该芳环并环丁烯类有机化合物的结构如通式(I)所示，其可作为掺杂材料用于电子器件的功能层中，提高器件的效率和寿命。
• Synthesis, spectroscopy and electrochemistry of phthalocyanine derivatives functionalised with four and eight peripheral tetrathiafulvalene units
  作者：Changsheng Wang、Martin R. Bryce、Andrei S. Batsanov、Claire F. Stanley、Andrew Beeby、Judith A. K. Howard

  DOI：10.1039/a701703k

  日期：——

  Metal-free phthalocyanine derivatives 2 and 14 bearing eight and four peripheral tetrathiafulvalene (TTF) units, respectively, have been synthesised, and their solution electrochemistry and optical spectroscopy have been studied. The compounds display redox properties arising from the TTF and from the phthalocyanine groups. 1H NMR and UV–VIS spectroscopic studies in solution show that aggregation is strongly solvent dependent. Quenching of the fluorescence of the phthalocyanine core by the TTF units was observed. The X-ray crystal structure of 4,5-bis(hexylthio)-4′,5′-bis(hydroxymethyl)-TTF 11, which was synthesised during the course of this work, has been determined. The hydroxy groups of 11 engage in intermolecular (and interstack) hydrogen bonds. Computer modelling studies on phthalocyanine derivatives 2 and 14 are reported.

  无金属酞菁衍生物2和14分别带有八个和四个外围的四硫富瓦烯（TTF）单元，已被合成，并研究了它们的溶液电化学和光学光谱。这些化合物表现出源自TTF和酞菁基团的氧化还原特性。溶液中的1H核磁共振和紫外-可见光谱研究显示，聚集强烈依赖于溶剂。观察到TTF单元对酞菁核心的荧光淬灭效应。在此工作中合成的4,5-双(己硫基)-4',5'-双(羟甲基)-TTF 11的X射线晶体结构已被测定。11的羟基参与了分子间（及堆叠间）的氢键。报告了关于酞菁衍生物2和14的计算机模拟研究。