2,6-diethynyl-4-methoxyaniline

Base Information

• Chemical Name: 2,6-diethynyl-4-methoxyaniline
• CAS No.: 1597511-69-7
• Molecular Formula: C₁₁H₉NO
• Molecular Weight: 171.199
• Mol file: 1597511-69-7.mol

Synonyms:2,6-diethynyl-4-methoxyaniline

Chemical Property of 2,6-diethynyl-4-methoxyaniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-diethynyl-4-methoxyaniline

There total 3 articles about 2,6-diethynyl-4-methoxyaniline 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: 97.0%

4-methoxy-2,6-bis((trimethylsilyl)ethynyl)aniline → 2,6-diethynyl-4-methoxyaniline (1597511-69-7)

Guidance literature:

With potassium hydroxide; In methanol; Schlenk technique; Inert atmosphere;

DOI:10.1021/ic402539x

Reference yield:

2,6-dibromo-4-methoxyaniline (95970-05-1) → 2,6-diethynyl-4-methoxyaniline (1597511-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / tetrahydrofuran / 48 h / 60 °C / Schlenk technique; Inert atmosphere

2: potassium hydroxide / methanol / Schlenk technique; Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; 1: |Sonogashira Cross-Coupling;

DOI:10.1021/ic402539x

Reference yield:

4-methoxy-aniline (104-94-9) → 2,6-diethynyl-4-methoxyaniline (1597511-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tetra-N-butylammonium tribromide / dichloromethane; methanol / 0.67 h / 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / 14 h / 80 °C / Inert atmosphere; Sealed tube

3: potassium carbonate / dichloromethane; methanol / 3 h / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-N-butylammonium tribromide; potassium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1039/c5cc00698h

upstream raw materials:

2,6-dibromo-4-methoxyaniline

4-methoxy-aniline

Downstream raw materials:

2,6-bis(3-pyridylethynyl)-4-methoxyaniline