4-(p-tolylthio)phthalonitrile | 183059-86-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(p-tolylthio)phthalonitrile
• 英文别名: 4-(4-Methylphenyl)sulfanylbenzene-1,2-dicarbonitrile
• CAS: 183059-86-1
• 化学式: C₁₅H₁₀N₂S
• 分子量: 250.324
• InChiKey: OFRWJSFSIHMYAF-UHFFFAOYSA-N

物化性质

• 沸点：
  478.6±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(p-tolylthio)phthalonitrile 在 氨 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 酞青
  参考文献：
  名称：

  Synthesis of Novel Unsymmetrically Substituted Push-Pull Phthalocyanines

  摘要：

  The synthesis and characterization of novel non-centrosymmetrically push-pull substituted metal-free phthalocyanines 3-9 are described. The compounds have different donor (dialkoxy, tert-butyl, methyl, p-tolylthio) and/or attractor (p-tolylsulfinyl, p-tolylsulfonyl, nitro) functional groups, are soluble in organic solvents, and are especially designed to study their second- and third-order nonlinear optical properties. Compounds 7-9 are mixtures of the four corresponding regioisomers. For preparing the unsymmetrical phthalocyanines 7-9, the effectiveness of the subphthalocyanine route, using different substituted diiminoisoindolines as reagents, has been tested. Furthermore, a comparison between this method versus the statistical one has been done. The results obtained show that the ring enlargement reaction of subphthalocyanines to obtain unsymmetrically substituted phthalocyanines is not a selective reaction but a multistep process, which depends dramatically on the nature of the substituents on the subphthalocyanines, the reactivity of the iminoisoindoline, the solvent, and other factors that limit its general synthetic utility. Preliminary data of the experimental second-order hyperpolarizabilities of compounds 3-9 are also given.

  DOI：

  10.1021/jo961018o
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 4-甲苯硫酚 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以79 %的产率得到4-(p-tolylthio)phthalonitrile
  参考文献：
  名称：

  Synthesis of 4-methylthiophenyl silicon phthalocyanines axially substituted with carboxylic acids for MOF materials

  摘要：

  利用微波辐照合成了两种新的外围被 4 个和 8 个电子供体取代的 4-甲基噻吩基硅酞菁，[式：见正文]1 和[式：见正文]2，轴向被羧酸取代，收率非常高。新化合物通过 1H-NMR、UV-vis、荧光、微分脉冲伏安图和 HR-MALDI-TOF 质谱进行了表征。对轴向氯化 SiPcs 的稳定性与噻吩取代基数目关系的研究表明，[式：见正文] 10 比[式：见正文]更快降解为相应的无反应二氢硅酞菁衍生物[式：见正文]11。新的 SiPcs 是构建 MOF 材料的光活性连接体的极佳候选材料。

  DOI：

  10.1142/s1088424622500961

文献信息

• A diastereoselective process induced in a curved aromatic molecule: oxidation of thioether-substituted subphthalocyanines
  作者：David González-Rodríguez、Tomás Torres

  DOI：10.1016/j.tetlet.2008.11.126

  日期：2009.2

  Different sulfoxide-substituted subphthalocyanines have been synthesized by oxidation reaction of the corresponding thioether precursors. We have observed for the first time that when the oxidation takes place close to the macrocyclic core, the intrinsically chiral subphthalocyanine can induce a high degree of diastereoselectivity in this process. (C) 2008 Elsevier Ltd. All rights reserved.
• RESIN BLENDS CONTAINING A PHTHALONITRILE REACTIVE DILUENT AND A DIPHTHALONITRILE RESIN, PREPREGS, AND ARTICLES
  申请人：3M Innovative Properties Company

  公开号：EP3601215A1

  公开（公告）日：2020-02-05
• [EN] RESIN BLENDS CONTAINING A PHTHALONITRILE REACTIVE DILUENT AND A DIPHTHALONITRILE RESIN, PREPREGS, AND ARTICLES<br/>[FR] MÉLANGES DE RÉSINES CONTENANT UN DILUANT RÉACTIF DE PHTALONITRILE ET UNE RÉSINE DE DIPHTALONITRILE, PRÉIMPRÉGNÉS ET ARTICLES
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2018175025A1

  公开（公告）日：2018-09-27

  The present disclosure provides a resin blend. The resin blend includes at least one diluent containing a single phthalonitrile functional group and at least one diphthalonitrile resin. Also provided are prepregs including the resin blend impregnated into continuous reinforcing fibers or a cloth. Similarly, the present disclosure provides a molding compound including chopped reinforcing fibers distributed in the resin blend. An article is also provided, which includes polymerization product of the resin blend. An alternative article includes a substrate and a layer of the resin blend disposed on the substrate. The diluent typically improves processability of the resin blend and lowers the softening temperature of the polymerization product of the resin blend.
• Synthesis of Novel Unsymmetrically Substituted Push-Pull Phthalocyanines
  作者：Ángela Sastre、Belén del Rey、Tomás Torres

  DOI：10.1021/jo961018o

  日期：1996.1.1

  The synthesis and characterization of novel non-centrosymmetrically push-pull substituted metal-free phthalocyanines 3-9 are described. The compounds have different donor (dialkoxy, tert-butyl, methyl, p-tolylthio) and/or attractor (p-tolylsulfinyl, p-tolylsulfonyl, nitro) functional groups, are soluble in organic solvents, and are especially designed to study their second- and third-order nonlinear optical properties. Compounds 7-9 are mixtures of the four corresponding regioisomers. For preparing the unsymmetrical phthalocyanines 7-9, the effectiveness of the subphthalocyanine route, using different substituted diiminoisoindolines as reagents, has been tested. Furthermore, a comparison between this method versus the statistical one has been done. The results obtained show that the ring enlargement reaction of subphthalocyanines to obtain unsymmetrically substituted phthalocyanines is not a selective reaction but a multistep process, which depends dramatically on the nature of the substituents on the subphthalocyanines, the reactivity of the iminoisoindoline, the solvent, and other factors that limit its general synthetic utility. Preliminary data of the experimental second-order hyperpolarizabilities of compounds 3-9 are also given.
• Synthesis of 4-methylthiophenyl silicon phthalocyanines axially substituted with carboxylic acids for MOF materials
  作者：Víctor Sobrino-Bastán、Luis Martín-Gomis、Ángela Sastre-Santos

  DOI：10.1142/s1088424622500961

  日期：2023.1

  Two new peripherally substituted with 4 and 8 electron-donating 4-methylthiophenyl silicon phthalocyanines, [Formula: see text] 1 and [Formula: see text] 2, axially substituted with carboxylic acids have been synthesized using microwave irradiation in a very good yield. The new compounds have been characterized by ¹H-NMR, UV-vis, fluorescence, differential pulse voltammograms, and HR-MALDI-TOF mass spectrometry. An study of the stability of the axial chlorinated SiPcs in the function of the number of thiophenyl substituents indicates than [Formula: see text] 10 degradates faster, to its corresponding unreactive dihydrosilicon phthalocyanine derivative [Formula: see text] 11, than [Formula: see text]. The new SiPcs are excellent candidates as photoactive linkers for the construction of MOF materials.

  利用微波辐照合成了两种新的外围被 4 个和 8 个电子供体取代的 4-甲基噻吩基硅酞菁，[式：见正文]1 和[式：见正文]2，轴向被羧酸取代，收率非常高。新化合物通过 1H-NMR、UV-vis、荧光、微分脉冲伏安图和 HR-MALDI-TOF 质谱进行了表征。对轴向氯化 SiPcs 的稳定性与噻吩取代基数目关系的研究表明，[式：见正文] 10 比[式：见正文]更快降解为相应的无反应二氢硅酞菁衍生物[式：见正文]11。新的 SiPcs 是构建 MOF 材料的光活性连接体的极佳候选材料。