[1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile

Base Information

• Chemical Name: [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile
• CAS No.: 1554027-03-0
• Molecular Formula: C₂₅H₁₉N₃
• Molecular Weight: 361.446
• Mol file: 1554027-03-0.mol

Synonyms:

Chemical Property of [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile

There total 4 articles about [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile 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:

4-(3-methyl-3-hydroxy-1-butynyl)-N,N-dimethylaniline (56512-48-2) → [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile (1554027-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate / toluene; acetone / 1 h / Inert atmosphere; Reflux

2: diisopropylamine; copper(l) iodide; triphenylphosphine; palladium diacetate / tetrahydrofuran / 3.5 h / Inert atmosphere; Reflux

3: pyridine / 23 h / 80 °C / Inert atmosphere

With pyridine; copper(l) iodide; potassium tert-butylate; palladium diacetate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; acetone; toluene; 2: |Sonogashira Cross-Coupling / 3: |Knoevenagel Condensation;

DOI:10.1016/j.tetlet.2014.01.002

Reference yield:

4-Iodo-N,N-dimethylaniline (698-70-4) → [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile (1554027-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisopropylamine / tetrahydrofuran / 0.33 h / 70 °C / Inert atmosphere

1.2: 5 h / Inert atmosphere

2.1: potassium tert-butylate / toluene; acetone / 1 h / Inert atmosphere; Reflux

3.1: diisopropylamine; copper(l) iodide; triphenylphosphine; palladium diacetate / tetrahydrofuran / 3.5 h / Inert atmosphere; Reflux

4.1: pyridine / 23 h / 80 °C / Inert atmosphere

With pyridine; copper(l) iodide; potassium tert-butylate; palladium diacetate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; acetone; toluene; 1.1: |Sonogashira Cross-Coupling / 1.2: |Sonogashira Cross-Coupling / 3.1: |Sonogashira Cross-Coupling / 4.1: |Knoevenagel Condensation;

DOI:10.1016/j.tetlet.2014.01.002

Reference yield:

1-(6-hydroxy-2-naphthyl)ethan-1-one (10441-41-5) → [1-(6-{[4-(dimethylamino)phenyl]ethynyl}naphthalen-2-yl)ethylidene]propanedinitrile (1554027-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 2 h / -15 °C / Inert atmosphere; Sealed tube

2: diisopropylamine; copper(l) iodide; triphenylphosphine; palladium diacetate / tetrahydrofuran / 3.5 h / Inert atmosphere; Reflux

3: pyridine / 23 h / 80 °C / Inert atmosphere

With pyridine; copper(l) iodide; palladium diacetate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; 2: |Sonogashira Cross-Coupling / 3: |Knoevenagel Condensation;

DOI:10.1016/j.tetlet.2014.01.002

upstream raw materials:

1-(6-hydroxy-2-naphthyl)ethan-1-one

6-acetylnaphthalen-2-yl trifluoromethanesulfonate

4-ethynyl-N,N-dimethylaniline

4-(3-methyl-3-hydroxy-1-butynyl)-N,N-dimethylaniline