4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

Base Information

Chemical Name:4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine
CAS No.:1206832-99-6
Molecular Formula:C₂₀H₂₁NO₂S₂
Molecular Weight:371.524
Hs Code.:

Synonyms:4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

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Chemical Property of 4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

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Technology Process of 4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

There total 3 articles about 4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine 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: 71.0%

: 1086450-04-5
4,4,5,5-tetramethyl-2-(5-(5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophen-2-yl)-thiophen-2-yl)-1,3,2-dioxaborolane

: 106-40-1
4-bromo-aniline

: 1206832-99-6
4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; for 12h; Inert atmosphere; Reflux;
DOI:10.1021/ol9026182

Reference yield:

: 4805-22-5
5,5'-dibromo-2,2'-bisthiophene

: 1206832-99-6
4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

Guidance literature:: Multi-step reaction with 4 steps

1.1: trichlorophosphate; n-butyllithium / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling; Schlenk technique

1.2: 50 °C / Inert atmosphere; Cooling; Schlenk technique

2.1: toluene-4-sulfonic acid / benzene / 5 h / Inert atmosphere; Reflux; Schlenk technique

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere; Schlenk technique

3.2: Inert atmosphere; Schlenk technique

4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux; Schlenk technique

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; trichlorophosphate; In tetrahydrofuran; hexane; water; benzene; 4.1: |Suzuki Coupling;
DOI:10.1002/chem.201201500

Reference yield:

: 1372699-62-1
2-(5'-bromo-2,2'-bithiophen-5-yl)-5,5-dimethyl-1,3-dioxane

: 1206832-99-6
4-[5'-(5,5-dimethyl-1,3-dioxan-2-yl)[2,2'-bithiophen]-5-yl]benzenamine

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: Inert atmosphere; Schlenk technique

2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux; Schlenk technique

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; water; 2.1: |Suzuki Coupling;
DOI:10.1002/chem.201201500