2,5-二氯-3-苯基噻吩 | 132981-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2,5-二氯-3-苯基噻吩
• 英文名称: 2,5-dichloro-3-phenylthiophene
• CAS: 132981-59-0
• 化学式: C₁₀H₆Cl₂S
• 分子量: 229.13
• InChiKey: QACGCGZDQNWOQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-二氯-3-苯基噻吩 在 三苯基膦 、 nickel dichloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 3-苯基噻吩
  参考文献：
  名称：

  从 2,5-二氯噻吩合成 3,4'-二芳基-和 4,4'-二芳基-2,2'-二噻吩基

  摘要：

  3,4'-二芳基-和 4,4'-二芳基-2,2'-二噻吩基，新类别的混合噻吩-芳烃低聚物，由 2,5-二氯噻吩通过 4-芳基-2-氯噻吩在三个过程中合成和两个步骤，分别。即，4-芳基-2-氯噻吩的Friedel-Crafts 型自缩合，然后催化脱氯，产生不对称的二噻吩基。使用镍-膦催化剂对 4-芳基-2-氯噻吩进行均偶联得到对称的二噻吩基。

  DOI：

  10.1246/bcsj.64.864
• 作为产物：
  描述：

  2-氯-4-苯基噻吩 在 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 60.0h， 以50%的产率得到2,5-二氯-3-苯基噻吩
  参考文献：
  名称：

  从 2,5-二氯噻吩合成 3,4'-二芳基-和 4,4'-二芳基-2,2'-二噻吩基

  摘要：

  3,4'-二芳基-和 4,4'-二芳基-2,2'-二噻吩基，新类别的混合噻吩-芳烃低聚物，由 2,5-二氯噻吩通过 4-芳基-2-氯噻吩在三个过程中合成和两个步骤，分别。即，4-芳基-2-氯噻吩的Friedel-Crafts 型自缩合，然后催化脱氯，产生不对称的二噻吩基。使用镍-膦催化剂对 4-芳基-2-氯噻吩进行均偶联得到对称的二噻吩基。

  DOI：

  10.1246/bcsj.64.864

文献信息

• METHOD FOR MANUFACTURING CONJUGATED AROMATIC COMPOUND
  申请人：Oda Seiji

  公开号：US20110275859A1

  公开（公告）日：2011-11-10

  A method for manufacturing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (A) does not have (c1) a group represented by the following formula (10): wherein A 1 represents a C1-C20 alkoxy group etc.; (g1) a C1-C20 alkyl group which may be substituted with a fluorine atom etc.; and (h1) a C2-C20 acyl group which may be substituted with a fluorine atom etc., at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) wherein the aromatic compound (B) is structurally different from the above-mentioned aromatic compound (A), one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (B) does not have the above-mentioned (c1), (g1) and (h1) at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, in the presence of (i) a nickel compound, (ii) a metal reducing agent, (iii) at least one ligand (L1) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-withdrawing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-withdrawing group and having no substituent at 2- and 9-positions, and (iv) at least one ligand (L2) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-releasing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-releasing group and having no substituent at 2- and 9-positions.

  一种制备共轭芳香化合物的方法，包括将含有一个或两个离去基团的芳香化合物（A）与含有相同结构的上述芳香化合物（A）或结构不同的芳香化合物（B）反应，其中这些离去基团选自碘原子、溴原子和氯原子，与芳香环结合，而芳香化合物（A）没有以下式（10）所代表的基团：其中A1代表C1-C20烷氧基等；（g1）代表C1-C20烷基基团，可能被氟原子等取代；以及（h1）代表C2-C20酰基基团，可能被氟原子等取代，与离去基团结合的碳原子的相邻碳原子处没有上述（c1）、（g1）和（h1），在（i）镍化合物、（ii）金属还原剂、（iii）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L1），具有至少一个吸电子基团且在3-、6-、3′-和6′-位置没有取代基，以及（iv）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L2），具有至少一个释电子基团且在3-、6-、3′-和6′-位置没有取代基团的情况下，在上述离去基团结合的碳原子的相邻碳原子处进行反应。
• BIPYRIDINE COMPOUND, TRANSITION METAL COMPLEX, AND METHOD FOR PRODUCTION OF CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20100184978A1

  公开（公告）日：2010-07-22

  A bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 each independently represent a C1-C10 alkyl group which may be substituted etc., and R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom etc., a transition metal complex obtained by contacting a bipyridine compound represented by the formula (1) with a compound of a transition metal belonging to Group 9, 10 or 11, and a method for production of a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of the transition metal complex.

  一种以式(1)表示的联吡啶化合物：其中R1、R2和R3各自独立地表示可以被取代的C1-C10烷基等，而R4、R5、R6、R7和R8各自独立地表示氢原子等，通过将式(1)表示的联吡啶化合物与属于9、10或11族过渡金属的化合物接触而获得的过渡金属配合物，以及一种制备共轭芳香化合物的方法，包括在过渡金属配合物的存在下，将一个或两个离去基团与芳环结合的芳香化合物（A）与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或结构不同于上述芳香化合物（A）且具有一个或两个离去基团与芳环结合的芳香化合物（B）反应。
• TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20110046336A1

  公开（公告）日：2011-02-24

  A transition metal complex obtained by contacting a bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 represent a C1-C10 alkyl group which may be substituted, etc., and R 4 and R 5 represent a hydrogen atom etc., with a compound of a transition metal belonging to Group 9, 10 or 11, and a process for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of said transition metal complex.

  通过将式（1）所表示的联吡啶化合物与属于9、10或11族的过渡金属化合物接触而获得的过渡金属配合物，其中R1、R2和R3代表C1-C10烷基，可以被取代等，而R4和R5代表氢原子等。制备共轭芳香化合物的方法包括，在所述过渡金属配合物的存在下，将一个芳香化合物（A），其中一个或两个离去基团与芳香环相键合，与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或在结构上不同于上述芳香化合物（A）并且具有一个或两个离去基团与芳香环相键合的芳香化合物（B）反应。
• Electrochemical Selective Mono‐ and Polychlorination of Substituted Thiophenes
  作者：Ting Liu、Hao‐Kuan Lu、Zhaojiang Shi、Hong Yan、Zhen Li、Ke‐Yin Ye

  DOI：10.1002/ejoc.202300880

  日期：2024.1.2

  A green and efficient electrochemical method for the selective monochlorination, dichlorination, and trichlorination of 2-substituted thiophenes has been developed.

  开发了一种绿色高效的电化学方法，用于 2-取代噻吩的选择性一氯化、二氯化和三氯化。
• METHOD FOR PRODUCING POLYARYLENE
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2065420A1

  公开（公告）日：2009-06-03

  A method for producing a polyarylene comprising polymerizing only a dihalobiphenyl compound represented by the formula (1): wherein A represents a C1-C20 alkoxy group etc., R1 represents a fluorine atom etc., X1 represents a chlorine atom etc., and k represents an integer of 0 to 3, or a dihalobiphenyl compound represented by the formula (1) with an aromatic compound represented by the formula (2): or an aromatic compound represented by the formula (3):         X3-Ar5-X3     (3) wherein a, b and c represents 0 or 1, n represents an integer of 5 or more, Ar1, Ar2, Ar3 and Ar4 represents a divalent aromatic group etc., Y1 and Y2 represents a single bond etc., Z1 and Z2 represents -O- or -S-, and X2 and X3 represent a chlorine atom etc., in the presence of catalytic amounts of a divalent nickel compound, a trivalent phosphorus ligand and zinc.

  一种生产聚芳基烯的方法，包括仅聚合由式（1）表示的二卤代联苯化合物： 其中 A 代表 C1-C20 烷氧基等，R1 代表氟原子等，X1 代表氯原子等，k 代表 0 至 3 的整数，或式（1）代表的二卤代联苯化合物与式（2）代表的芳香族化合物聚合： 或式（3）代表的芳香族化合物： X3-Ar5-X3 (3) 其中 a、b 和 c 代表 0 或 1，n 代表 5 或 5 以上的整数，Ar1、Ar2、Ar3 和 Ar4 代表二价芳香基团等，Y1 和 Y2 代表单键等，Z1 和 Z2 代表 -O- 或 -S-，X2 和 X3 代表氯原子等、 在催化量的二价镍化合物、三价磷配体和锌的存在下。