1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene

Base Information

• Chemical Name: 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene
• CAS No.: 406721-51-5
• Molecular Formula: C₆₅H₈₅BrO₈Si
• Molecular Weight: 1102.37

Synonyms:1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene

Chemical Property of 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene

There total 12 articles about 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene 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: 39.0%

1,4-dipropyloxy-2-ethynyl-5-(2-triisopropylsilylethinyl)benzene (221292-51-9) + 1,4-bis(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxybenzene (406721-50-4) → 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene (406721-51-5)

Guidance literature:

With piperidine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 60 ℃; for 6h;

DOI:10.1002/1099-0690(200112)2001:23<4431::aid-ejoc4431>3.0.co;2-j

Reference yield:

1,4-dipropoxybenzene (3898-41-7) → 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene (406721-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / Br₂; NaOAc / acetic acid / 12 h / 20 °C

2: 77 percent / iodine; KIO₃; H₂SO₄ / H₂O; acetic acid; CCl₄ / 5 h / Heating

3: 85 percent / PPh₃; piperidine / PdCl₂(PPh₄)2/CuI / 12 h

4: 84 percent / PPh₃; piperidine / PdCl₂(PPh₄)2/CuI / 12 h

5: 65 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h

6: 39 percent / PPh₃; piperidine / PdCl₂(PPh₄)2/CuI / 6 h / 60 °C

With piperidine; potassium iodate; sulfuric acid; bromine; iodine; sodium acetate; potassium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; methanol; tetrachloromethane; water; acetic acid; 3: Hagihara-Sonogashira reaction / 4: Hagihara-Sonogashira reaction / 6: Hagihara-Sonogashira reaction;

DOI:10.1002/1099-0690(200112)2001:23<4431::aid-ejoc4431>3.0.co;2-j

Reference yield:

hydroquinone (123-31-9,8027-02-9) → 1-[4-(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(triisopropylsilylethynyl)phenylethynyl]-2,5-dipropoxybenzene (406721-51-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / KOH / ethanol / 2 h / Heating

2: 76 percent / Br₂; NaOAc / acetic acid / 12 h / 20 °C

3: 77 percent / iodine; KIO₃; H₂SO₄ / H₂O; acetic acid; CCl₄ / 5 h / Heating

4: 85 percent / PPh₃; piperidine / PdCl₂(PPh₄)2/CuI / 12 h

5: 84 percent / PPh₃; piperidine / PdCl₂(PPh₄)2/CuI / 12 h

6: 65 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h

7: 39 percent / PPh₃; piperidine / PdCl₂(PPh₄)2/CuI / 6 h / 60 °C

With piperidine; potassium iodate; potassium hydroxide; sulfuric acid; bromine; iodine; sodium acetate; potassium carbonate; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; water; acetic acid; 4: Hagihara-Sonogashira reaction / 5: Hagihara-Sonogashira reaction / 7: Hagihara-Sonogashira reaction;

DOI:10.1002/1099-0690(200112)2001:23<4431::aid-ejoc4431>3.0.co;2-j

upstream raw materials:

1,4-dipropyloxy-2-ethynyl-5-(2-triisopropylsilylethinyl)benzene

1,4-bis(4-bromo-2,5-dipropoxyphenylethynyl)-2,5-dipropoxybenzene

1,4-dipropoxybenzene

hydroquinone

Downstream raw materials:

1-[4-(2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[4-(2,5-dipropoxy-4-ethynylphenylethynyl)phenylethynyl]-2,5-dipropoxybenzene

1-[4-(2,5-dipropoxyphenylethynyl)-2,5-dipropoxyphenylethynyl]-4-[2,5-dipropoxy-4-(2,5-dipropoxy-4-triisopropylsilylethynylphenylethynyl)phenylethynyl]-2,5-dipropoxybenzene

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