7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde

Base Information

• Chemical Name: 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde
• CAS No.: 1509939-07-4
• Molecular Formula: C₇₁H₉₅NO₃S₂
• Molecular Weight: 1074.67
• Mol file: 1509939-07-4.mol

Synonyms:7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde

Chemical Property of 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde

There total 16 articles about 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde 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: 54.0%

4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline (1221821-41-5) + 7-bromo-4,9-dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde (1509939-05-2) → 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde (1509939-07-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/ol402749s

Reference yield:

4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline (1146433-75-1) → 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde (1509939-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine; periodic acid / ethanol / 1 h / Reflux; Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere

3: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 24 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; potassium acetate; potassium carbonate; periodic acid; In ethanol; dimethyl sulfoxide; toluene; 3: |Suzuki Coupling;

DOI:10.1021/ol402749s

Reference yield:

1-iodo-4-hexyloxybenzene (85557-94-4) → 7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexylsindaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde (1509939-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide; copper(l) chloride; 1,10-Phenanthroline / toluene / 12 h / 100 °C / Inert atmosphere; Reflux

2: iodine; periodic acid / ethanol / 1 h / Reflux; Inert atmosphere

3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere

4: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 24 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,10-Phenanthroline; iodine; potassium acetate; potassium carbonate; periodic acid; copper(l) chloride; potassium hydroxide; In ethanol; dimethyl sulfoxide; toluene; 4: |Suzuki Coupling;

DOI:10.1021/ol402749s

upstream raw materials:

1-iodo-4-hexyloxybenzene

4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-phenylaniline

4-(hexyloxy)-N-(4-(hexyloxy)phenyl)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline

7-bromo-4,9-dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b']dithiophene-2-carbaldehyde

Downstream raw materials:

2-cyano-3-{7-{4-[N,N-bis(4-hexyloxyphenyl)amino]phenyl}-4,9-dihydro-4,4,9,9-tetrahexyl-s-indaceno[1,2-b:5,6-b']dithiophene-2-yl}acrylic acid