2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene

Base Information

• Chemical Name: 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene
• CAS No.: 1431043-00-3
• Molecular Formula: C₂₀H₁₄OS₂
• Molecular Weight: 334.463
• Mol file: 1431043-00-3.mol

Synonyms:2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene

Chemical Property of 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene

There total 5 articles about 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)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: 50.0%

5-bromo-2-methoxythiophene (57070-77-6) + trimethyl((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)silane (1428770-31-3) → 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene (1431043-00-3)

Guidance literature:

With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; benzyltri(n-butyl)ammonium chloride; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; In water; toluene; at 40 ℃; for 18h; Inert atmosphere;

DOI:10.1002/chem.201203672

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene (1431043-00-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: zinc; triphenylphosphine / 25 h / 0 - 20 °C / Inert atmosphere

2.2: 19 h / 0 - 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.1: 1,4-diaza-bicyclo[2.2.2]octane; tri-tert-butyl phosphine; bis(benzonitrile)palladium(II) dichloride / acetonitrile / 18 h / 20 °C / Inert atmosphere

5.1: bis(benzonitrile)palladium(II) dichloride; tri tert-butylphosphoniumtetrafluoroborate; benzyltri(n-butyl)ammonium chloride; sodium hydroxide; copper(l) iodide / toluene; water / 18 h / 40 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; benzyltri(n-butyl)ammonium chloride; triethylamine; triphenylphosphine; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; zinc; lithium diisopropyl amide; In tetrahydrofuran; water; toluene; acetonitrile; 5.1: |Sonogashira Cross-Coupling;

DOI:10.1002/chem.201203672

Reference yield:

4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0) → 2-methoxy-5-((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)thiophene (1431043-00-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc; triphenylphosphine / 25 h / 0 - 20 °C / Inert atmosphere

1.2: 19 h / 0 - 20 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.1: 1,4-diaza-bicyclo[2.2.2]octane; tri-tert-butyl phosphine; bis(benzonitrile)palladium(II) dichloride / acetonitrile / 18 h / 20 °C / Inert atmosphere

4.1: bis(benzonitrile)palladium(II) dichloride; tri tert-butylphosphoniumtetrafluoroborate; benzyltri(n-butyl)ammonium chloride; sodium hydroxide; copper(l) iodide / toluene; water / 18 h / 40 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; benzyltri(n-butyl)ammonium chloride; triphenylphosphine; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; zinc; lithium diisopropyl amide; In tetrahydrofuran; water; toluene; acetonitrile; 4.1: |Sonogashira Cross-Coupling;

DOI:10.1002/chem.201203672

upstream raw materials:

4-(trimethylsilylethynyl)phenylacetylene

5-bromo-2-methoxythiophene

trimethyl((4-((5-methylthiophen-2-yl)ethynyl)phenyl)ethynyl)silane

4-[(trimethylsilyl)ethynyl]bezaldehyde