2,2'-Bithiophene, 5-(4-methylphenyl)-

Base Information

• Chemical Name: 2,2'-Bithiophene, 5-(4-methylphenyl)-
• CAS No.: 106925-77-3
• Molecular Formula: C15H12S2
• Molecular Weight: 256.392
• Mol file: 106925-77-3.mol

Synonyms:

Chemical Property of 2,2'-Bithiophene, 5-(4-methylphenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,2'-Bithiophene, 5-(4-methylphenyl)-

There total 3 articles about 2,2'-Bithiophene, 5-(4-methylphenyl)- 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: 90.0%

para-bromotoluene (106-38-7) + 2,2'-Bithiophene (492-97-7) → 5-(p-tolyl)-2,2'-bithiophene (106925-77-3) + 5,5'-bis(4-methylphenyl)-2,2'-bithiophene

Guidance literature:

With C₄₀H₃₆N₂O₂Pd⁽²⁺⁾*2C₂H₄O₂; potassium carbonate; Trimethylacetic acid; In N,N-dimethyl acetamide; at 100 ℃; for 24h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/jo402745b

Reference yield: 78.0%

C15H10S (1446230-02-9) → 5-(p-tolyl)-2,2'-bithiophene (106925-77-3)

Guidance literature:

With copper(l) iodide; sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 90 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c5ra15705f

Reference yield:

2-(2,2-dibromovinyl)thiophene (77295-66-0) + 4-n-methylphenylacetylene (766-97-2) → 5-(p-tolyl)-2,2'-bithiophene (106925-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium phosphate; tert-butyl acetoacetate; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere; Schlenk technique

2: copper(l) iodide; sodiumsulfide nonahydrate / N,N-dimethyl-formamide / 6 h / 90 °C / Inert atmosphere; Schlenk technique

With potassium phosphate; copper(l) iodide; sodiumsulfide nonahydrate; tert-butyl acetoacetate; In N,N-dimethyl-formamide;

DOI:10.1039/c5ra15705f

upstream raw materials:

para-bromotoluene

2,2'-Bithiophene

2-(2,2-dibromovinyl)thiophene

4-n-methylphenylacetylene

Refernces

• 1、 Li, Yabo,Wang, Jingran,Huang, Mengmeng,Wang, Zhiwei,Wu, Yusheng,Wu, Yangjie. "Direct C-H arylation of thiophenes at low catalyst loading of a phosphine-free bis(alkoxo)palladium complex". . p. 2890 - 2897. Retrieved 2014/05/06.