对氯硝基苯二聚体 | 110972-79-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 对氯硝基苯二聚体
• 英文名称: E-azodioxy-4-chlorobenzene
• 英文别名: p-chloronitrosobenzene dimer；(E)-bis-(4-chloro-phenyl)-diazene-N,N'-dioxide；(E)-Bis-(4-chlor-phenyl)-diazen-N,N'-dioxid；(E)-(4-chlorophenyl)-[(4-chlorophenyl)-oxidoazaniumylidene]-oxidoazanium
• CAS: 110972-79-7
• 化学式: C₁₂H₈Cl₂N₂O₂
• 分子量: 283.114
• InChiKey: WOLOJDCIELGJEA-FOCLMDBBSA-N

物化性质

• 沸点：
  435.0±55.0 °C(Predicted)
• 密度：
  1.437±0.06 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：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对氯硝基苯二聚体 在 甲醇 、 sodium methylate 作用下， 生成 4,4-二氯氧化偶氮苯
  参考文献：
  名称：

  Miller; Parker, Australian Journal of Chemistry, 1958, vol. 11, p. 302,307

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯亚硝基苯 以 potassium bromide 为溶剂， 生成 对氯硝基苯二聚体
  参考文献：
  名称：

  Photothermal Reactions of Nitrosobenzene and Halonitrosobenzenes in Solid-state

  摘要：

  Photothermal reactions of the dimers of nitrosobenzene, m-chloronitrosobenzene, and p-chloronitrosobenzene were studied in solid-state by IR spectroscopy at low temperatures and by X-ray powder diffraction. It was found for the first time that photothermal cycle (photolytic dissociation followed by thermal dimerization) could successively be performed also with Z-configured dimeric nitrosobenzene.Halonitrosobenzenes dimers with E-configuration afforded different photo behavior depending on the position of halogen atom on the benzene ring: while m-halonitrosobenzenes do not dissociate under UV irradiation, p-chloronitrosobenzene, as well as previously studied p-bromonitrosobenzene photolyses very efficiently with recovering of the original crystal phase. Kinetics of thermal dimerization was measured in solid-state, and it was found that the reaction phase transformation occurs as a two-dimensional growth through the crystal. (doi: 10.5562/cca1714)

  DOI：

  10.5562/cca1714

文献信息

• Oxidation of aromatic amines with hydrogen peroxide catalyzed by cetylpyridinium heteropolyoxometalates
  作者：Sigeki Sakaue、Takashi Tsubakino、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo00066a012

  日期：1993.7

  Various substituted anilines 1 were selectively converted into the corresponding nitrosobenzenes 2 or nitrobenzenes 3 by oxidation with aqueous hydrogen peroxide catalyzed by heteropolyoxometalates. The oxidations of anilines 1 with 35% H2O2 catalyzed by peroxotungstophosphate (PCWP) at room temperature in chloroform under two-phase conditions afforded nitrosobenzenes 2 with high selectivity. When the same reactions were carried out at higher temperature (e.g., refluxing chloroform), nitrobenzenes 3 were obtained in good yields. The oxidation of aniline (1a) with dilute H2O2 catalyzed by PCWP (2 wt %) in an aqueous medium produced azoxybenzene (4a) with high selectivity. Phenylazoxyalkanes 7 were prepared by the first direct cooxidation of la in the presence of primary aliphatic amines 6. For example, the oxidation of a 1:2 mixture of 1a and hexylamine (6b) with 35 % H2O2 (6 equiv) in the presence of PCWP produced phenylazoxyhexane (7b) (51 %) along with a small amount of 4a (8 %). The reaction path for the conversion of anilines to azoxy-, nitroso-, and nitrobenzenes is described.