4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate)

Base Information

• Chemical Name: 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate)
• CAS No.: 1378950-71-0
• Molecular Formula: C₃₀H₄₄F₆O₆S₂Si₂
• Molecular Weight: 734.969
• Mol file: 1378950-71-0.mol

Synonyms:4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate)

Chemical Property of 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate)

There total 4 articles about 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate) 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: 46.0%

4,5-diiodo-1,2-phenylene bis(trifluoromethanesulfonate) (1378950-54-9) + tris-iso-propylsilyl acetylene (89343-06-6) → 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate) (1378950-71-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201200079

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate) (1378950-71-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine; periodic acid / methanol / 5 h / 70 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 4 h / 0 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 5 h / 0 °C / Inert atmosphere

3.2: 6.1 h / 20 °C / Inert atmosphere

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

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; boron tribromide; periodic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 4.1: Sonogashira coupling;

DOI:10.1002/ejoc.201200079

Reference yield:

1,2-diiodo-4,5-dimethoxybenzene (110190-08-4) → 4,5-bis[2-(triisopropylsilyl)ethynyl]-1,2-phenylene bis(trifluoromethane-sulfonate) (1378950-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron tribromide / dichloromethane / 4 h / 0 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 5 h / 0 °C / Inert atmosphere

2.2: 6.1 h / 20 °C / Inert atmosphere

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

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; boron tribromide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Sonogashira coupling;

DOI:10.1002/ejoc.201200079

upstream raw materials:

4,5-diiodo-1,2-phenylene bis(trifluoromethanesulfonate)

tris-iso-propylsilyl acetylene

1,2-dimethoxybenzene

1,2-diiodo-4,5-dimethoxybenzene

Refernces