4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile

Base Information

• Chemical Name: 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile
• CAS No.: 1389321-72-5
• Molecular Formula: C₅₂H₃₇N₃S₂
• Molecular Weight: 768.018

Synonyms:4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile

Chemical Property of 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile

Chemical Property:

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Technology Process of 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile

There total 7 articles about 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile 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: 90.0%

2-[N,N-bis-(9,9-dimethylfluoren-2-yl)aminophenyl]-5,5'-bithiophene-2' boronic acid pinacol ester (1389321-71-4) + 4-iodo-1,2-dicyanobenzene (69518-17-8) → 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile (1389321-72-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; at 95 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201200020

Reference yield:

2-[N,N-bis-(9,9-dimethylfluoren-2-yl)aminophenyl]-2'-bromo-5,5'-bisthiophene (1383782-66-8) → 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile (1389321-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 24 h / 95 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water; 2.1: Suzuki coupling;

DOI:10.1002/chem.201200020

Reference yield:

2-bromo-9,9-dimethyl-9H-fluorene (28320-31-2) → 4-[2-(N,N-bis-(9,9-dimethylfluoren-2-yl)-4-aminophenyl)-5,5'-bisthiophene-2']phthalonitrile (1389321-72-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / toluene / 20 h / Inert atmosphere; Reflux

2.1: N-Bromosuccinimide / chloroform / 1 h / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 20 h / Inert atmosphere; Reflux

4.1: N-Bromosuccinimide / chloroform / 1 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

5.2: 1 h / 0 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 24 h / 95 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium tert-butylate; potassium carbonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; chloroform; water; toluene; 3.1: Suzuki coupling / 6.1: Suzuki coupling;

DOI:10.1002/chem.201200020

upstream raw materials:

2-[N,N-bis-(9,9-dimethylfluoren-2-yl)aminophenyl]-2'-bromo-5,5'-bisthiophene

2-[N,N-bis-(9,9-dimethylfluoren-2-yl)aminophenyl]-5,5'-bithiophene-2' boronic acid pinacol ester

4-iodo-1,2-dicyanobenzene

2-bromo-9,9-dimethyl-9H-fluorene

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