6-hexyl-2-phenylazulene

Base Information

• Chemical Name: 6-hexyl-2-phenylazulene
• CAS No.: 1431768-11-4
• Molecular Formula: C₂₂H₂₄
• Molecular Weight: 288.433
• Mol file: 1431768-11-4.mol

Synonyms:6-hexyl-2-phenylazulene

Chemical Property of 6-hexyl-2-phenylazulene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-hexyl-2-phenylazulene

There total 7 articles about 6-hexyl-2-phenylazulene 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%

2-bromo-6-hexylazulene (1431768-26-1) + phenylboronic acid (98-80-6) → 6-hexyl-2-phenylazulene (1431768-11-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; at 100 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.084

Reference yield:

hex-1-yne (693-02-7) → 6-hexyl-2-phenylazulene (1431768-11-4)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 2.5 h / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 20 °C

3: potassium hydroxide; water / ethanol / 4 h / Reflux

4: phosphoric acid / 0.33 h / 130 °C

5: phosphorus tribromide / toluene / 1 h / 100 °C

6: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; phosphoric acid; palladium 10% on activated carbon; water; hydrogen; phosphorus tribromide; caesium carbonate; triethylamine; potassium hydroxide; In 1,4-dioxane; ethanol; toluene; 1: |Sonogashira Cross-Coupling / 6: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.tet.2013.03.084

Reference yield:

diethyl 6-(1-hexynyl)-2-methoxyazulene-1,3-dicarboxylate (1431768-13-6) → 6-hexyl-2-phenylazulene (1431768-11-4)

Guidance literature:

Multi-step reaction with 5 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 20 °C

2: potassium hydroxide; water / ethanol / 4 h / Reflux

3: phosphoric acid / 0.33 h / 130 °C

4: phosphorus tribromide / toluene / 1 h / 100 °C

5: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; phosphoric acid; palladium 10% on activated carbon; water; hydrogen; phosphorus tribromide; caesium carbonate; potassium hydroxide; In 1,4-dioxane; ethanol; toluene; 5: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.tet.2013.03.084

upstream raw materials:

2-bromo-6-hexylazulene

phenylboronic acid

diethyl 6-bromo-2-methoxyazulene-1,3-dicarboxylate

hex-1-yne