5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde
• CAS No.: 1416172-52-5
• Molecular Formula: C₄₈H₅₇N₃OS₃
• Molecular Weight: 788.198

Synonyms:5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde

Chemical Property of 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde

Chemical Property:

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Technology Process of 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde

There total 4 articles about 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-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: 81.0%

4-(N-phenyl-N-p-tolylamino)phenylboronic acid (1228595-50-3) + 5-(5'-bromo-4,4'-dinonyl-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde (1416172-50-3) → 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde (1416172-52-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In tetrahydrofuran; water; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.dyepig.2012.10.002

Reference yield:

2-(2-thienyl)-1,3-dioxolane (58268-08-9) → 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde (1416172-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Trimethyl borate; hydrogenchloride; n-butyllithium / water / Inert atmosphere; Schlenk technique

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 48 h / 80 °C / Inert atmosphere; Schlenk technique

3: N-Bromosuccinimide; acetic acid / chloroform / Inert atmosphere; Schlenk technique

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / Inert atmosphere; Schlenk technique

With hydrogenchloride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Trimethyl borate; sodium carbonate; acetic acid; In tetrahydrofuran; chloroform; water; 2: |Suzuki Coupling / 4: |Suzuki Coupling;

DOI:10.1016/j.dyepig.2012.10.002

Reference yield:

methyl nonyl ketone (112-12-9) → 5-(4,4'-dinonyl-5'-(4-(phenyl(p-tolyl)amino)phenyl)-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde (1416172-52-5)

Guidance literature:

Multi-step reaction with 6 steps

1: bromine / methanol / Inert atmosphere; Schlenk technique

2: ethanol / Inert atmosphere; Schlenk technique

3: N-Bromosuccinimide / N,N-dimethyl-formamide / Inert atmosphere; Schlenk technique

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / 48 h / 80 °C / Inert atmosphere; Schlenk technique

5: N-Bromosuccinimide; acetic acid / chloroform / Inert atmosphere; Schlenk technique

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water / Inert atmosphere; Schlenk technique

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; sodium carbonate; acetic acid; In tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; 2: |Hantzsch Thiazole Synthesis / 4: |Suzuki Coupling / 6: |Suzuki Coupling;

DOI:10.1016/j.dyepig.2012.10.002

upstream raw materials:

4-(N-phenyl-N-p-tolylamino)phenylboronic acid

5-(5'-bromo-4,4'-dinonyl-2,2'-bithiazol-5-yl)thiophene-2-carbaldehyde

2-(2-thienyl)-1,3-dioxolane

methyl nonyl ketone

Downstream raw materials:

C₅₁H₅₈N₄O₂S₃

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