2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene

Base Information

• Chemical Name: 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene
• CAS No.: 635679-13-9
• Molecular Formula: C₂₁H₂₆SSi₂
• Molecular Weight: 366.674
• Mol file: 635679-13-9.mol

Synonyms:2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene

Chemical Property of 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene

There total 2 articles about 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene 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: 76.0%

trimethylsilylacetylene (1066-54-2) + 2-(2,5-dibromo-4-methyl-phenyl)-thiophene (635679-12-8) → 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene (635679-13-9)

Guidance literature:

With copper(l) iodide; diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 80 ℃; for 20h;

DOI:10.1002/anie.200352075

Reference yield:

2,5-Dibromo-4-iodotoluene (123568-21-8) → 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene (635679-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / [PdCl₂(PPh₃)2] / dimethylformamide / 12 h / 80 °C

2: 76 percent / CuI; diisopropylamine / [Pd(PPh₃)4] / toluene / 20 h / 80 °C

With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; toluene; 1: Stille cross-coupling / 2: Sonogashira cross-coupling;

DOI:10.1002/anie.200352075

Reference yield: 59.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene (635679-13-9) → 4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane (635679-14-0)

Guidance literature:

2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene; With tert.-butyl lithium; In tetrahydrofuran; at -70 ℃; for 1.5h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1002/anie.200352075

upstream raw materials:

trimethylsilylacetylene

2-(2,5-dibromo-4-methyl-phenyl)-thiophene

2,5-Dibromo-4-iodotoluene

Downstream raw materials:

4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-triisopropylsilanyloxy-benzaldehyde

2-hydroxy-4-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-benzaldehyde