1-iodyl-3-chlorobenzene | 16825-75-5

• 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: 1-iodyl-3-chlorobenzene
• 英文别名: 3-Chlorjodylbenzol；1-chloro-3-iodyl-benzene；1-Chlor-3-jodyl-benzol；m-Chloroiodoxybenzene；1-chloro-3-iodylbenzene
• CAS: 16825-75-5
• 化学式: C₆H₄ClIO₂
• 分子量: 270.454
• InChiKey: UFMTVUVOVQLCQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C(Solv: water (7732-18-5))

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 1-iodyl-3-chlorobenzene 在 sodium tetrachloropalladate 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 4.5h， 以88%的产率得到3-氯苯甲酸
  参考文献：
  名称：

  Simple and efficient palladium-catalyzed carbonylation of iodoxyarenes in water under mild conditions

  摘要：

  Iodoxyarenes (ArIO2) readily react with CO (1 atm) in water, in the presence of Na2[PdCl4] (0.1%) and Na2CO3 at 40-50-degrees-C, to give the corresponding carboxylic acids, ArCOOH, in 55-89% isolated yield. Particularly attractive features of the reaction are that, unlike most iodoarenes, ArIO2 can be carbonylated in aqueous media without any organic solvents, due to their solubility in water and high reactivity.

  DOI：

  10.1021/jo00070a008
• 作为产物：
  描述：

  3-bromoiodylbenzene 在 sodium hypochlorite 、 sodium tetrachloropalladate 、 sodium carbonate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 1-iodyl-3-chlorobenzene
  参考文献：
  名称：

  Simple and efficient palladium-catalyzed carbonylation of iodoxyarenes in water under mild conditions

  摘要：

  Iodoxyarenes (ArIO2) readily react with CO (1 atm) in water, in the presence of Na2[PdCl4] (0.1%) and Na2CO3 at 40-50-degrees-C, to give the corresponding carboxylic acids, ArCOOH, in 55-89% isolated yield. Particularly attractive features of the reaction are that, unlike most iodoarenes, ArIO2 can be carbonylated in aqueous media without any organic solvents, due to their solubility in water and high reactivity.

  DOI：

  10.1021/jo00070a008

文献信息

• RuCl₃-Catalyzed Oxidation of Iodoarenes with Peracetic Acid:  New Facile Preparation of Iodylarenes
  作者：Alexey Y. Koposov、Rashad R. Karimov、Andrey A. Pronin、Tatyana Skrupskaya、Mekhman S. Yusubov、Viktor V. Zhdankin

  DOI：10.1021/jo062073s

  日期：2006.12.1

  New facile methodology for the preparation of pentavalent iodine compounds using peracetic acid as an oxidant in the presence of catalytic amounts of ruthenium trichloride is described. The new procedure allows the preparation of several previously unknown iodylarenes bearing strongly electron-withdrawing CF3 groups in the aromatic ring.

  描述了在催化量的三氯化钌存在下使用过氧乙酸作为氧化剂制备五价碘化合物的新的简便方法。该新方法允许制备几种先前未知的在芳族环中带有强烈吸电子CF 3基团的异丁烯。
• Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species
  作者：Mekhman S. Yusubov、Victor N. Nemykin、Viktor V. Zhdankin

  DOI：10.1016/j.tet.2010.04.046

  日期：2010.7

  are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed

  报道了使用高价碘物质进行的几种过渡金属介导的氧化反应。已经开发了通过RuCl 3催化的碘代芳烃的氧化制备芳烃的简便方法。该程序允许产生高反应性的单体碘（V）物种，它们是原位对醇和碳氢化合物的极佳氧化剂。的宽范围的底物可以通过基于ARIO的钌（III）催化的再氧化到ARIO串联催化体系被氧化为羰基化合物2使用过硫酸氢钾®作为氧化剂。结果表明，亲电子碘（III）物种源自低聚的碘烷基苯硫酸盐（PhIO）3 SO 3是在金属卟啉配合物存在下催化氧化芳香烃的有效氧化剂。
• Mild and efficient synthesis of iodylarenes using Oxone as oxidant
  作者：Natalia Soldatova、Pavel Postnikov、Anna A. Troyan、Akira Yoshimura、Mekhman S. Yusubov、Viktor V. Zhdankin

  DOI：10.1016/j.tetlet.2016.08.038

  日期：2016.9

  Mild and efficient method for the preparation of iodylarenes by oxidation of iodoarenes with Oxone in aqueous acetonitrile at room temperature is described. This new procedure allows the preparation of various iodylarenes with electron-donating or electron-withdrawing substituents in the aromatic ring including the previously unknown 1,2-diiodylbenzene.

  描述了一种温和有效的方法，该方法通过在室温下在乙腈水溶液中用Oxone氧化碘代芳烃来氧化碘芳烃。该新方法允许制备各种芳族环中具有供电子或吸电子取代基的异丁烯，包括以前未知的1,2-二碘苯。
• Syntheses of (Diacetoxyiodo)arenes or Iodylarenes from Iodoarenes, with Sodium Periodate as the Oxidant
  作者：Pawel Kazmierczak、Lech Skulski、Lukasz Kraszkiewicz

  DOI：10.3390/61100881

  日期：——

  (diacetoxyiodo)-arenes, ArI(OAc)2, or iodylarenes, ArIO2, from the corresponding iodoarenes, ArI, using sodium periodate as the oxidant are presented in this paper. In order to obtain 2- and 4-iodylbenzoic acids, the respective sodium salts of 2- and 4-iodobenzoic acids should be used as the starting substrates, because mixtures containing the corresponding iodosyl derivatives as the main products

  - 本文介绍了使用高碘酸钠作为氧化剂从相应的碘芳烃 ArI 制备（二乙酰氧基碘）-芳烃 ArI(OAc)2 或碘代芳烃 ArIO2 的简单、安全和有效的新方法。为了获得 2- 和 4- 碘基苯甲酸，应使用 2- 和 4- 碘苯甲酸各自的钠盐作为起始底物，因为含有相应碘基衍生物作为主要产物以及预期碘基化合物的混合物是由游离母酸产生。
• Willgerodt, Chemische Berichte, 1893, vol. 26, p. 1947,1948
  作者：Willgerodt

  DOI：——

  日期：——