2-((4-bromophenyl)thio)aniline | 3169-86-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((4-bromophenyl)thio)aniline
• 英文别名: (2-aminophenyl)-4’-bromophenyl sulfide；2-(4-bromophenyl)sulfanylaniline
• CAS: 3169-86-6
• 化学式: C₁₂H₁₀BrNS
• 分子量: 280.188
• InChiKey: BTJMOALRSIKLMP-UHFFFAOYSA-N

物化性质

• 沸点：
  387.5±27.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 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：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-bromophenyl)-(2-nitrophenyl)thioether 在 镍 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 2-((4-bromophenyl)thio)aniline
  参考文献：
  名称：

  dibenz [b，f] -1,4-thiazepine，-oxazep​​ine和dibenz [b，e] -azepine系列内酰胺的新合成。4.关于七元杂环的通信†

  摘要：

  通过在分子内应用异氰酸根合-二苯基硫化物，-二苯氧化物和-二苯基甲烷与AlCl 3在邻二氯苯中的LEUCKART酰胺合成方法，发现了一种能够以非常好的收率得到10,11-dihydro-11-oxo-dibenz [b，f分别为-1,4-噻氮平（VII），-氧杂氮平（VIII）和5,6-二氢-6-氧杂二苯并[b，e]-氮杂平（XI）。

  DOI：

  10.1002/hlca.19650480212

文献信息

• Iron-Catalyzed S-Arylation of Benzothiazole with Aryl Iodides under Aqueous Medium: Facile Synthesis of Aryl(2-aminoaryl) Sulfides
  作者：Ka Yung、Fuk Kwong、Hang Lee

  DOI：10.1055/s-0034-1379484

  日期：——

  A simple route for facile access of aryl(2-aminoaryl) sulfide was reported. With the aid of iron(III) chloride catalyst and diamine ligand, benzothiazole was efficiently S-arylated with various aryl iodides (19 examples) in water under air atmosphere. This operationally simple protocol provides aryl(2-aminoaryl) sulfides in moderate to good yields.

  报道了一种容易获得芳基（2-氨基芳基）硫化物的简单途径。在氯化铁 (III) 催化剂和二胺配体的帮助下，苯并噻唑与各种芳基碘化物（19 个实例）在空气中在水中有效 S-芳基化。这种操作简单的方案以中等至良好的产率提供芳基（2-氨基芳基）硫化物。
• Copper Powder Catalyzed Direct Ring-Opening Arylation of Benzazoles with Aryl Iodides in Polyethylene Glycol
  作者：Lifang Yao、Qing Zhou、Wei Han、Shaohua Wei

  DOI：10.1002/ejoc.201201166

  日期：2012.12

  The expedient and efficient copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol that proceeds in the absence of an added ligand has been developed. The protocol provides facile access to 2-(arylthio)anilines and 2-phenoxyanilines in high yields with a wide tolerance of functional groups. Transmission electron microscopy confirmed that the active

  已经开发了方便且有效的铜粉催化苯并唑与芳基碘在聚乙二醇中的直接开环芳基化反应，该反应在没有添加配体的情况下进行。该协议提供了对 2-（芳硫基）苯胺和 2-苯氧基苯胺的高产率和广泛的官能团耐受性的轻松访问。透射电子显微镜证实，活性催化剂是在标准反应条件下原位生成铜纳米颗粒的结果，这是开发高效金属铜催化剂的另一种途径。此外，催化系统最多可循环使用六次。
• Thiolate-assisted copper(<scp>i</scp>) catalyzed C–S cross coupling of thiols with aryl iodides: scope, kinetics and mechanism
  作者：Sneha Prasad Bakare、Mahendra Patil

  DOI：10.1039/d2nj00043a

  日期：——

  Transition metal catalyzed coupling of thiols with aryl iodide offers a convenient method for accessing C–S linkage in organic synthesis. Herein, we report an efficient and practical method for the C–S cross coupling of thiophenols with aryl iodides using a Cu(I) catalyst. A diverse set of thiophenols is coupled with electron rich and poor aryl iodides to obtain diaryl sulfides in good to excellent

  硫醇与芳基碘的过渡金属催化偶联提供了一种在有机合成中获得 C-S 键的便捷方法。在此，我们报道了一种使用 Cu( I ) 催化剂实现苯硫酚与芳基碘化物的 C-S 交叉偶联的有效且实用的方法。一组不同的苯硫酚与富电子和贫电子芳基碘化物结合，以良好至优异的产率获得二芳基硫化物。值得注意的是，这些反应在极性质子溶剂和无配体环境下顺利进行。该方法也可用于通过容易获得的苯并噻唑的开环合成 2-氨基苯硫醚衍生物。此外，我们进行了动力学和计算研究以了解 Cu( I) 在没有配体的情况下催化反应。反应速率与取代基常数的哈米特图表明，这些偶联反应对苯硫酚和芳基碘上的取代基适度敏感，表明两种反应物都参与了反应的速率决定步骤。另一方面，对不同机理途径的计算研究表明，硫醇盐与 Cu 的强配位可能产生催化活性中间体 [Cu(SPh) 2 ]K，它可以启动催化循环。预计由[Cu(SPh) 2 ]K 引发的途径将通过相
• A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
  作者：Amit Kumar、Sangit Kumar

  DOI：10.1016/j.tet.2014.01.030

  日期：2014.3

  A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature. (C) 2014 Elsevier Ltd. All rights reserved.
• Unexpectedly ligand-free copper-catalyzed C–S cross-coupling of benzothiazole with aryl iodides in aqueous solution
  作者：Yi-Si Feng、Hong-Xia Qi、Wei-Cheng Wang、Yu-Feng Liang、Hua-Jian Xu

  DOI：10.1016/j.tetlet.2012.04.004

  日期：2012.6

  A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50 degrees C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield. (C) 2012 Elsevier Ltd. All rights reserved.