2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile

Base Information

• Chemical Name: 2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile
• CAS No.: 169966-50-1
• Molecular Formula: C₂₄H₁₄N₂
• Molecular Weight: 330.389
• Mol file: 169966-50-1.mol

Synonyms:2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile

Chemical Property of 2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile

There total 7 articles about 2-<4-(9-Anthracenyl)phenylmethylene>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: 66.0%

4-(anthracene-9-yl)benzaldehyde (169831-24-7) + malononitrile (109-77-3) → 2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile (169966-50-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.saa.2020.118153

Reference yield:

9-Bromoanthracene (1564-64-3) → 2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile (169966-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; potassium carbonate; tetrabutylammomium bromide / water / 70 °C / Inert atmosphere

2: triethylamine / dichloromethane / 20 °C

With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; triethylamine; In dichloromethane; water; 1: |Suzuki Coupling / 2: |Knoevenagel Condensation;

DOI:10.1016/j.saa.2020.118153

Reference yield:

anthracene (120-12-7) → 2-<4-(9-Anthracenyl)phenylmethylene>propanedinitrile (169966-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C

2: palladium diacetate; potassium carbonate; tetrabutylammomium bromide / water / 70 °C / Inert atmosphere

3: triethylamine / dichloromethane / 20 °C

With N-Bromosuccinimide; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; 2: |Suzuki Coupling / 3: |Knoevenagel Condensation;

DOI:10.1016/j.saa.2020.118153

upstream raw materials:

4-(anthracene-9-yl)benzaldehyde

malononitrile

1.4-dibromobenzene

anthracen-9(10H)-one

Downstream raw materials:

<<4-(9-Anthracenyl)phenyl><2-(2,4,6-cycloheptatrien-1-ylidene)methyl>methylene>propanedinitrile

Refernces

• 1、 Spreitzer, Hubert,Daub, Joerg. "Dihydroazulene/Vinylheptafulvene Photochromism: Effect of ?-Arylenes on the Switching Behavior". . p. 1637 - 1642. Retrieved 2007/10/02.