4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde

Base Information

• Chemical Name: 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde
• CAS No.: 1318689-68-7
• Molecular Formula: C₃₆H₂₄N₂O₃S
• Molecular Weight: 564.664
• Mol file: 1318689-68-7.mol

Synonyms:4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde

Chemical Property of 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde

There total 5 articles about 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde 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: 58.0%

2-tributylstannyl-5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophene + 5-bromo-2-formylbenzonitrile (523977-64-2) → 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde (1318689-68-7)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; In N,N-dimethyl-formamide; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c1jm10107b

Reference yield:

2-cyano-4-nitrotoluene (939-83-3) → 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde (1318689-68-7)

Guidance literature:

Multi-step reaction with 5 steps

1: zinc / methanol / 4 h / 20 °C / Inert atmosphere

2: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 5 h / 70 °C / Reflux; Inert atmosphere

3: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 9 h / 90 °C / Inert atmosphere

4: trimethylamine-N-oxide / dichloromethane; dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere; Cooling with ice

5: trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

With N-Bromosuccinimide; trans-bis(triphenylphosphine)palladium dichloride; trimethylamine-N-oxide; hydrogen bromide; copper(I) bromide; zinc; sodium nitrite; dibenzoyl peroxide; In methanol; tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 5: Stille coupling;

DOI:10.1039/c1jm10107b

Reference yield:

2-Methylbenzonitrile (529-19-1) → 4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)-2-cyanobenzaldehyde (1318689-68-7)

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid; nitric acid / 1 h / 20 °C / Inert atmosphere; Cooling with ice

2: zinc / methanol / 4 h / 20 °C / Inert atmosphere

3: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 5 h / 70 °C / Reflux; Inert atmosphere

4: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 9 h / 90 °C / Inert atmosphere

5: trimethylamine-N-oxide / dichloromethane; dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere; Cooling with ice

6: trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

With N-Bromosuccinimide; trans-bis(triphenylphosphine)palladium dichloride; trimethylamine-N-oxide; sulfuric acid; hydrogen bromide; nitric acid; copper(I) bromide; zinc; sodium nitrite; dibenzoyl peroxide; In methanol; tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 6: Stille coupling;

DOI:10.1039/c1jm10107b

upstream raw materials:

5-bromo-2-formylbenzonitrile

2-Methylbenzonitrile

2-cyano-4-nitrotoluene

3-cyano-4-methylaniline

Downstream raw materials:

(E)-3-(4-(5-(p-(naphthylphenylamino)phenyl)-3,4-ethylenedioxythiophen-2-yl)cyanophenyl)cyanoacrylic acid