5,5'-bis(phenylethynyl)-2,2'-dithiophene

Base Information

• Chemical Name: 5,5'-bis(phenylethynyl)-2,2'-dithiophene
• CAS No.: 115257-02-8
• Molecular Formula: C₂₄H₁₄S₂
• Molecular Weight: 366.507
• Mol file: 115257-02-8.mol

Synonyms:5,5'-bis(phenylethynyl)-2,2'-dithiophene

Chemical Property of 5,5'-bis(phenylethynyl)-2,2'-dithiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5'-bis(phenylethynyl)-2,2'-dithiophene

There total 5 articles about 5,5'-bis(phenylethynyl)-2,2'-dithiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.6%

5,5'-dibromo-2,2'-bisthiophene (4805-22-5) + phenylacetylene (536-74-3) → 5,5'-bis(phenylethynyl)-2,2'-dithiophene (115257-02-8)

Guidance literature:

copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine; In various solvent(s); at 70 ℃; for 4h;

DOI:10.1002/hlca.19960790318

Reference yield: 63.0%

2,2'-Bithiophene (492-97-7) + phenylacetylene (536-74-3) → 5-(2-phenylethynyl)-2,2'-bithiophene (4805-21-4) + 5,5'-bis(phenylethynyl)-2,2'-dithiophene (115257-02-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; triethylamine; silver(l) oxide; Trimethylacetic acid; In 1,2-dimethoxyethane; at 90 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.201210013

Reference yield: 52.0%

2-(phenylethynyl)thiophene (4805-17-8) + N, N-dimethylthiophene-2-carboxamide (30717-57-8) → C19H15NOS2 (1430206-26-0) + 5,5'-bis(phenylethynyl)-2,2'-dithiophene (115257-02-8)

Guidance literature:

With palladium diacetate; silver(l) oxide; 2-Biphenylcarboxylic acid; In dimethyl sulfoxide; at 80 ℃; for 8h;

DOI:10.1039/c3sc51278a

upstream raw materials:

5,5'-dibromo-2,2'-bisthiophene

phenylacetylene

2,2'-Bithiophene

2-(phenylethynyl)thiophene

Downstream raw materials:

2,5'-bis[Co2(CO)6(μ-η2:η2-C(C6H5)C)]bithiophene

Refernces

• 1、 Dahlmann, Uwe,Neidlein, Richard. "Palladium-catalyzed syntheses of polyethynyl-substituted 2,2′-bithiophenes". . p. 755 - 766. Retrieved 1996.
• 2、 Li, Ren-Hao,Ding, Zong-Cang,Li, Cun-Yao,Chen, Jun-Jia,Zhou, Yun-Bing,An, Xiao-Ming,Ding, Yun-Jie,Zhan, Zhuang-Ping. "Thiophene-Alkyne-Based CMPs as Highly Selective Regulators for Oxidative Heck Reaction". supporting information. p. 4432 - 4435. Retrieved 2017/09/11.
• 3、 He, Chun-Yang,Wang, Zhen,Wu, Cai-Zhi,Qing, Feng-Ling,Zhang, Xingang. "Pd-catalyzed oxidative cross-coupling between two electron rich heteroarenes". . p. 3508 - 3513. Retrieved 2013/11/19.