(5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene

Base Information

• Chemical Name: (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene
• CAS No.: 1252668-51-1
• Molecular Formula: C₁₈H₁₄N₂O₂S₂
• Molecular Weight: 354.453
• Mol file: 1252668-51-1.mol

Synonyms:

Chemical Property of (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene

There total 5 articles about (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene 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:

2-chlorobenzylthiocyanate (2082-66-8) + 5,5'-bis(2-oxobutyl)-2,2'-bithiophene (1252668-65-7) → (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene (1252668-51-1) + C24H20ClNO2S2 (1268591-50-9)

Guidance literature:

5,5'-bis(2-oxobutyl)-2,2'-bithiophene; With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

2-chlorobenzylthiocyanate; In tetrahydrofuran; at 20 ℃; Further stages; Inert atmosphere;

DOI:10.1021/cm102109p

Reference yield:

1-(2-thienyl)-2-butanol (126435-93-6) → (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene (1252668-51-1) + C24H20ClNO2S2 (1268591-50-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridinium chlorochromate / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / benzene / Inert atmosphere; Reflux

3.1: potassium fluoride; bis(benzonitrile)palladium(II) dichloride; silver nitrate / dimethyl sulfoxide / 60 °C / Inert atmosphere

4.1: hydrogenchloride; water / tetrahydrofuran / Inert atmosphere; Reflux

5.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

With hydrogenchloride; potassium fluoride; bis(benzonitrile)palladium(II) dichloride; water; toluene-4-sulfonic acid; silver nitrate; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1021/cm102109p

Reference yield:

1-(2-thienyl)butan-2-one ethylene acetal (1252668-59-9) → (5Z,5'Z)-5,5'-bis(α-cyano-α-propionylmethylene)-5,5'-dihydro-Δ2,2'-bithiophene (1252668-51-1) + C24H20ClNO2S2 (1268591-50-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium fluoride; bis(benzonitrile)palladium(II) dichloride; silver nitrate / dimethyl sulfoxide / 60 °C / Inert atmosphere

2.1: hydrogenchloride; water / tetrahydrofuran / Inert atmosphere; Reflux

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With hydrogenchloride; potassium fluoride; bis(benzonitrile)palladium(II) dichloride; water; silver nitrate; lithium diisopropyl amide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/cm102109p

upstream raw materials:

5,5'-bis(2-oxobutyl)-2,2'-bithiophene bis(ethylene acetal)

2-chlorobenzylthiocyanate

5,5'-bis(2-oxobutyl)-2,2'-bithiophene

1-(2-thienyl)butan-2-one ethylene acetal

Refernces