N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide

Base Information

• Chemical Name: N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide
• CAS No.: 926643-79-0
• Molecular Formula: C₅₂H₆₂N₂O₄Si₂
• Molecular Weight: 835.246
• Mol file: 926643-79-0.mol

Synonyms:N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide

Chemical Property of N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide

There total 3 articles about N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide 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: 76.0%

N,N′-bis(n-octyl)-2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic diimide (926643-78-9) + 4-(trimethylsilylethynyl)-1-(trimethylstannyl)benzene (16116-84-0) → N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide (926643-79-0)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 120 ℃; for 15h;

DOI:10.1039/b615085c

Reference yield:

2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride (83204-68-6) → N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide (926643-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 28 percent / acetic acid / 1 h / 130 °C

2: 76 percent / Pd(PPh₃)4 / toluene / 15 h / 120 °C

With acetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; 2: Stille coupling;

DOI:10.1039/b615085c

Reference yield:

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → N,N'-dioctyl-2,6-(4'-trimethylsilylethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide (926643-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / sulfuric acid; dibromoisocyanuric acid / 15 h / 130 °C

2: 28 percent / acetic acid / 1 h / 130 °C

3: 76 percent / Pd(PPh₃)4 / toluene / 15 h / 120 °C

With sulfuric acid; acetic acid; dibromoisocyanuric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; 3: Stille coupling;

DOI:10.1039/b615085c

upstream raw materials:

N,N′-bis(n-octyl)-2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic diimide

4-(trimethylsilylethynyl)-1-(trimethylstannyl)benzene

1,4,5,8-naphthalenetetracarboxylic dianhydride

2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride

Downstream raw materials:

N,N'-dioctyl-2,6-(4'-ethynylphenyl)naphthalene-1,4,5,8-tetracarboxylic acid bisimide