2,3,4-tribromo-5-(p-tolyl)thiophene | 1332705-18-6

• 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: 2,3,4-tribromo-5-(p-tolyl)thiophene
• 英文别名: 2,3,4-Tribromo-5-(4-methylphenyl)thiophene
• CAS: 1332705-18-6
• 化学式: C₁₁H₇Br₃S
• 分子量: 410.955
• InChiKey: KEYPFJAABQMPEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2,3,4-tribromo-5-(p-tolyl)thiophene 在 四(三苯基膦)钯 、 potassium phosphate 、 (cyclobutene-1,2-diyl)bis-imidazolium tetrafluoroborate 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 甲苯 、 乙腈 为溶剂， 反应 48.33h， 生成 4-(4-methoxyphenyl)-2-(o-tolyl)-5-(p-tolyl)thiophene
  参考文献：
  名称：

  四环噻吩-1,2-二基双咪唑鎓预配体对四溴噻吩的选择性单芳基到全芳基化

  摘要：

  （环丁-1-烯-1,2-二基）双（1-甲基咪唑鎓）四氟硼酸酯作为预配体应用于钯催化的从四溴噻吩开始的交叉偶联反应中，以合成单，双，三和四芳基-取代的噻吩带有多达四个不同的芳基环。通过仅使用一个单一的催化剂体系就可以提供一种合成试剂盒，该试剂盒用于制备九种不同的芳基化噻吩取代模式。与DFT计算（预测三芳基-3-溴噻吩和四芳基噻吩在能量上较低的旋转势垒）一致，在相邻的芳基环之间未检测到NOE效应。因此，通过将三芳基-3-溴噻吩还原为2,3,5-三芳基噻吩，随后进行HMBC，HSQC和NOESY NMR测量，阐明了它们合成的区域选择性。此外，

  DOI：

  10.1021/jo201317t
• 作为产物：
  描述：

  4-甲苯硼酸 、 四溴噻吩 在 potassium phosphate 、 (cyclobutene-1,2-diyl)bis-imidazolium tetrafluoroborate 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 以81%的产率得到2,3,4-tribromo-5-(p-tolyl)thiophene
  参考文献：
  名称：

  用作钯催化交叉偶联反应前体的环丁烯-1,2-双（咪唑鎓）盐：性质和应用

  摘要：

  介绍了标题双咪唑鎓盐、其单卡宾和双卡宾及其与钯的相互作用的光谱研究和计算结果。此外，我们报告了用标题双咪唑盐进行的金属催化交叉偶联反应的范围和局限性。该盐被证明是室温 Suzuki-Miyaura 反应、C-C 与空间位阻极强联芳基偶联、选择性噻吩芳基化以及与氯乙烯偶联的有效配体前体。

  DOI：

  10.1002/ejoc.201101378

文献信息

• Pd-Catalyzed one-pot sequential cross-coupling reactions of tetrabromothiophene
  作者：Kapil Mohan Saini、Rakesh K. Saunthwal、Akhilesh K. Verma

  DOI：10.1039/c7ob02601c

  日期：——

  sequential cross-coupling reactions of sterically hindered tetrabromothiophene with arylboronic acid and an alkyne/alkene to afford selective bi-, tri-, and tetrasubstituted aryl/alkynyl-thiophenes with the aid of a palladium catalyst were described. The reaction proceeds via a site-selective Suzuki/Sonogashira coupling, followed by selective Sonogashira, Suzuki and Heck coupling reactions. This methodology

  描述了空间受阻的四溴噻吩与芳基硼酸和炔烃/烯烃的不对称单锅顺序交叉偶联反应，借助于钯催化剂可得到选择性的双，三和四取代的芳基/炔基噻吩。该反应通过位点选择性的Suzuki / Sonogashira偶联进行，然后进行选择性的Sonogashira，Suzuki和Heck偶联反应。该方法论证明了有机支架合成的重要框架。
• METHOD FOR PRODUCING STRUCTURE WHEREIN AROMATIC POLYMER IS BONDED TO BASE, STRUCTURE HAVING AROMATIC POLYMER CHAIN BONDED TO CONDUCTIVE BASE, AND ELECTRONIC DEVICE COMPRISING THE STRUCTURE
  申请人：Tanaka Kenta

  公开号：US20100069603A1

  公开（公告）日：2010-03-18

  Disclosed is a method for efficiently producing a structure wherein an aromatic polymer is bonded to a base. Also disclosed is such a structure wherein the base is electrically conductive. Specifically disclosed is a method for producing a structure, which comprises a step for polycondensing an aromatic compound represented by the formula (I) below in the presence of a polymerization catalyst and a base having a group represented by the formula (II) below. MY n Ar—X  (I) (In the formula (I), Ar represents a divalent group composed of an aromatic ring; X represents a halogen atom or the like; Y represents an oxygen atom, a sulfur atom, an imino group or the like; n represents 0 or 1; and M represents a hydrogen atom, —B(OQ 1 ) 2 (wherein Q 1 represents a hydrogen atom, a hydrocarbon group or the like) or the like.) —Ar a —(X a ) p (II) (In the formula (II), Ar a represents a group having a valence of (p+1) and composed of an aromatic ring; X a represents a halogen atom or a monovalent group expressed as —SO 3 Q a (wherein Q a represents a substituted or unsubstituted hydrocarbon group); p represents an integer not less than 1, and when p is an integer not less than 2, the plurality of X a 's may be the same as or different from each other.)

  公开了一种高效生产芳香族聚合物与基体结合的结构的方法。还公开了这样一种结构，其中基体具有电导性。具体公开了一种生产结构的方法，该方法包括在聚合催化剂和具有以下式子（II）中表示的基团的碱存在下，聚合表示为以下式子（I）的芳香族化合物的步骤。MYnAr—X  (I)（在式（I）中，Ar表示由芳香族环组成的二价基团；X表示卤素原子或类似物；Y表示氧原子、硫原子、亚胺基或类似物；n表示0或1；M表示氢原子，-B（OQ1）2（其中Q1表示氢原子、碳氢基团或类似物）或类似物。）—Ara—（Xa）p（II）（在式（II）中，Ararepresents具有（p+1）价且由芳香族环组成的基团；Xarepresents卤素原子或表示为-SO3Qa的一价基团（其中Qarepresents取代或未取代的碳氢基团）；p表示不小于1的整数，当p为不小于2的整数时，Xa的多个可以相同也可以不同。）
• Crafting diverse tetraphenylthiophene designs through comprehensive ‘classical’ Suzuki-Miyaura synthesis and electrochemical exploration
  作者：Sudhakar Maddala、Kalidass Kollimalaian、Ankita Samal、Venkatakrishnan Parthasarathy

  DOI：10.1016/j.tet.2023.133807

  日期：2024.1

  successful programmed synthesis of diverse designs of tetraphenylthiophene derivatives (TPTs, 16 out of 24 probable structures) and the intermediate triphenylthiophene derivatives (12 out of 20 probable structures) using optimized ‘classical’ Suzuki-Miyaura cross-coupling conditions through multiple routes starting from a single precursor, tetrabromothiophene. Our first-ever electrochemical analysis of various

  我们通过多种途径，使用优化的“经典”Suzuki-Miyaura 交叉偶联条件，成功编程合成了不同设计的四苯基噻吩衍生物（TPT，24 种可能结构中的 16 种）和中间体三苯基噻吩衍生物（20 种可能结构中的 12 种）从单一前体四溴噻吩开始。我们对各种 TPT 设计的首次电化学分析强调了电子不同芳基单元的排列对 TPT 氧化电位的关键影响。这些发现提供了对 TPT 设计氧化还原趋势的见解，可能指导 TPT 中的选择性氧化 C-C 偶联以实现 π 扩展的噻吩。
• LAMINATED STRUCTURE, METHOD FOR PRODUCING SAME, AND ELECTRONIC ELEMENT COMPRISING SAME
  申请人：Tanaka Kenta

  公开号：US20110177312A1

  公开（公告）日：2011-07-21

  A laminated structure comprising an electrode, a polymer binding layer arranged on the electrode, and an electrically conductive organic material layer arranged on the polymer binding layer, wherein the polymer binding layer comprises an aromatic polymeric compound which has a structure represented by formula (I) [wherein Ar represents a conjugated divalent group which may have a substituent, provided that when there are multiple Ar's, the Ar's may be the same as or different from each other; and n represents an integer of 1 or greater] and has a number average molecular weight of 1×10 3 to 1×10 8 inclusive in terms of polystyrene content, the polymer binding layer is bonded to the electrode via a chemical bond between the aromatic polymeric compound and the surface of the electrode, and an electrically conductive organic material that composes a layer included in the electrically conductive organic material layer and arranged adjacent to the polymer binding layer has a number average molecular weight of 3×10 2 to 1×10 8 inclusive in terms of polystyrene content.