(2-碘苯基)(4-硝基苯基)硫醚 | 1042413-89-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (2-碘苯基)(4-硝基苯基)硫醚
• 英文名称: (2-iodophenyl)(4-nitrophenyl)thioether
• 英文别名: (2-iodophenyl)(4-nitrophenyl)sulfane；(iodophenyl)(4-nitrophenyl)sulfane；1-Iodo-2-(4-nitrophenyl)sulfanylbenzene
• CAS: 1042413-89-7
• 化学式: C₁₂H₈INO₂S
• 分子量: 357.172
• InChiKey: KOJIKXMPMMETNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-碘苯基)(4-硝基苯基)硫醚 、 2-溴硫代苯酚 在 tris(dibenzylideneacetone)dipalladium (0) 1,1'-双(二苯基膦)二茂铁 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以69%的产率得到1-(2-bromophenylthio)-2-(4-nitrophenylthio)benzene
  参考文献：
  名称：

  Synthesis of molecular chains: phenylene thioether and sulfoxide oligomers

  摘要：

  The application of a general synthetic approach to prepare molecular chains is reported. It is based on a step-by-step method each consisting first in a Pd-catalyzed reaction between ArI and HXAr'Br (Ar=aryl, Ar'=arylene) to give ArXAr'Br followed by a Cu-catalyzed replacement of Br by I to give ArXAr'I that can be reacted with HXAr'Br in the following step. The application of this method is here illustrated to prepare phenylene sulfide oligomers (X=S). Starting from RC6H4I-4 (R=H, MeO, NO2, NH2) and HSC6H4BF-x (x=2, 4) it is possible to grow chains in one direction to give X(C6H4S-m)(n)C6H4R-4 (n=1, X=Br, m=4, R=H, MeO, NO2, NH2, SMe and m=2, R=H, MeO, NO2; n=1, X=I, m=2 or 4, R=H, MeO, NO2; n=2, X=Br, m=2 or 4, R=H, MeO, NO2; n=2, X=I, m=4, R=MeO, NO2; n=3, X=Br, m=4, R=MeO, NO2; n=3, X=I, m=4, R=NO2 and n=4, X=Br or I, m=4, R=NO2). From HSC6H4Br-x and IC6H4I-4 the chains can grow in two directions to give X(C6H4S-4)(n)C6H4X-4 (n=2 or 4, X=Br or I), 2-XC6H4(SC6H4-4)(n)SC6H4X-2 (n=3 or 5, X=Br). Using diiodomesitylene the dithioethers C6HMe3-2,4,6-(SC6H4X-4)(2)-1,3 (X=Br, I) have been prepared. The series of sulfoxides X(C6H4S(O)-4)(n)C6H4R-4 (X=Br, n=1, R=MeO, n=3, R=NO2, n=4, R=Br; X=R=I, n=2) has been obtained from the corresponding thioethers and PhICl2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.108
• 作为产物：
  描述：

  (2-bromophenyl)(4-nitrophenyl)sulfane 在 copper(l) iodide 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以75%的产率得到(2-碘苯基)(4-硝基苯基)硫醚
  参考文献：
  名称：

  Synthesis of molecular chains: phenylene thioether and sulfoxide oligomers

  摘要：

  The application of a general synthetic approach to prepare molecular chains is reported. It is based on a step-by-step method each consisting first in a Pd-catalyzed reaction between ArI and HXAr'Br (Ar=aryl, Ar'=arylene) to give ArXAr'Br followed by a Cu-catalyzed replacement of Br by I to give ArXAr'I that can be reacted with HXAr'Br in the following step. The application of this method is here illustrated to prepare phenylene sulfide oligomers (X=S). Starting from RC6H4I-4 (R=H, MeO, NO2, NH2) and HSC6H4BF-x (x=2, 4) it is possible to grow chains in one direction to give X(C6H4S-m)(n)C6H4R-4 (n=1, X=Br, m=4, R=H, MeO, NO2, NH2, SMe and m=2, R=H, MeO, NO2; n=1, X=I, m=2 or 4, R=H, MeO, NO2; n=2, X=Br, m=2 or 4, R=H, MeO, NO2; n=2, X=I, m=4, R=MeO, NO2; n=3, X=Br, m=4, R=MeO, NO2; n=3, X=I, m=4, R=NO2 and n=4, X=Br or I, m=4, R=NO2). From HSC6H4Br-x and IC6H4I-4 the chains can grow in two directions to give X(C6H4S-4)(n)C6H4X-4 (n=2 or 4, X=Br or I), 2-XC6H4(SC6H4-4)(n)SC6H4X-2 (n=3 or 5, X=Br). Using diiodomesitylene the dithioethers C6HMe3-2,4,6-(SC6H4X-4)(2)-1,3 (X=Br, I) have been prepared. The series of sulfoxides X(C6H4S(O)-4)(n)C6H4R-4 (X=Br, n=1, R=MeO, n=3, R=NO2, n=4, R=Br; X=R=I, n=2) has been obtained from the corresponding thioethers and PhICl2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.108

文献信息

• 一种硫酚与邻二碘苯的反应方法
  申请人：苏州大学

  公开号：CN113620848A

  公开（公告）日：2021-11-09

  本发明公开了一种硫酚与邻二碘苯的反应方法，以硫酚与邻二碘苯为底物，在金属氢化物存在下、溶剂中反应，完成硫酚与邻二碘苯的反应，得到邻碘苯硫醚。本发明在NaH作用下，利用邻二碘苯与苯硫酚发生亲核反应生成邻碘苯硫醚产物。该方法无需过渡金属参与即完成了C‑S键偶联，操作简便，无金属试剂残留、污染等问题；同时，与现有前体相比，邻二碘苯价格便宜，方便制备，具有更好的原子经济性；其生成的产物苯硫醚邻位有一个碘，能够很方便的进行其他转化得到各种各样的1,2‑取代苯，特别的，只需要3当量的金属氢化物就可取得优异收率。
• Copper-Assisted (Pseudo-)Halochalcogenation of Arynes
  作者：Jasper Mindner、Sina Rombach、Daniel B. Werz

  DOI：10.1021/acs.orglett.4c00498

  日期：2024.3.15

  In this report, we describe the multicomponent coupling reaction between arynes, (pseudo)halides, and an electrophilic chalcogen species. Addition of a copper salt enabled smooth conversion by suppressing side reactions. A variety of different aryne precursors as well as seleno- and thiosulfonates were employed, yielding a broad spectrum of ortho-(pseudo)halogenated chalcogenides. This motif was subjected

  在本报告中，我们描述了芳炔、（拟）卤化物和亲电子硫族元素之间的多组分偶联反应。添加铜盐可以抑制副反应，从而实现顺利的转化。采用了各种不同的芳基前体以及硒代磺酸盐和硫代磺酸盐，产生了广谱的邻（拟）卤化硫属化物。该基序采用了不同的交叉偶联方法，证明了这些化合物作为更复杂结构的构建模块的适用性。
• The Reaction of Aryl Thiols or Thioureas with o‐Diiodoarenes/NaH to Access o‐Iodoaryl Thioethers
  作者：Min Hu、Dianfan Liu、Yuan Liu、Fan Luo、Xiaobei Chen、Yuejia Yin、Shilei Zhang、Yanwei Hu

  DOI：10.1002/adsc.202301426

  日期：2024.4.9

  synthesis of thioethers by forging C(aryl)-S bond via an aryne mechanism. The active aryne species can be generated from o-diiodoarenes and NaH in THF at room temperature, then lead to the arylations of a wide range of aryl thiols and thioureas. Different from transition metal-catalyzed cross-coupling reactions, no disubstituted byproduct is formed in our protocol. The o-iodoaryl thioether products are

  在此，我们报道了一种通过芳基机理形成 C(芳基)-S 键来合成硫醚的方法。室温下，邻二碘芳烃和 NaH 在 THF 中可以生成活性芳炔，然后导致多种芳基硫醇和硫脲的芳基化。与过渡金属催化的交叉偶联反应不同，我们的方案中没有形成双取代的副产物。邻碘芳基硫醚产品是可以转化为药学上感兴趣的分子的中间体。