N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine

Base Information

• Chemical Name: N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine
• CAS No.: 1404053-06-0
• Molecular Formula: C₃₂H₃₂BNO₂
• Molecular Weight: 473.423
• Mol file: 1404053-06-0.mol

Synonyms:N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine

Chemical Property of N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine

There total 2 articles about N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-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: 60.0%

N-{4-[2-(4-bromophenyl)vinyl]phenyl}-diphenylamine (219987-44-7) + bis(pinacol)diborane (73183-34-3) → N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine (1404053-06-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; triphenylphosphine; In toluene; at 120 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c2cc35754b

Reference yield:

1-bromo-4-ethenyl-benzene (2039-82-9) + 4-(N,N-diphenylamino)iodobenzene (38257-52-2) → N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine (1404053-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 36 h / 60 °C / Inert atmosphere; Alkaline conditions

2: bis-triphenylphosphine-palladium(II) chloride; potassium acetate; triphenylphosphine / toluene / 24 h / 120 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium acetate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; toluene; 1: |Heck Reaction / 2: |Miyaura Borylation Reaction;

DOI:10.1039/c2cc35754b

Reference yield: 88.0%

4,7-bis(5-bromothiophen-2-yl)-5,6-bis(tetradecyloxy)benzo[c][1,2,5]thiadiazole (1192352-10-5) + N,N-diphenyl-4-[2-[4-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)phenyl]ethenyl]-benzenamine (1404053-06-0) → 4,7-bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-ethenyl}phenyl}-2-thienyl}-5,6,-bis(otcyloxy)-2,1,3-benzothiadiazole (1404053-08-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; water; toluene; at 110 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c2cc35754b

upstream raw materials:

1-bromo-4-ethenyl-benzene

4-(N,N-diphenylamino)iodobenzene

N-{4-[2-(4-bromophenyl)vinyl]phenyl}-diphenylamine

bis(pinacol)diborane

Downstream raw materials:

4,7-bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-ethenyl}phenyl}-2-thienyl}-5,6,-bis(otcyloxy)-2,1,3-benzothiadiazole

C₈₂H₇₈N₄O₂S₂

Refernces

• 1、 Zeng, Shaohang,Yin, Lunxiang,Ji, Changyan,Jiang, Xueying,Li, Kechang,Li, Yanqin,Wang, Yue. "D-π-A-π-D type benzothiadiazole-triphenylamine based small molecules containing cyano on the π-bridge for solution-processed organic solar cells with high open-circuit voltage". . p. 10627 - 10629. Retrieved 2012/11/07.