N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline

Base Information

• Chemical Name: N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline
• CAS No.: 248276-95-1
• Molecular Formula: C₃₂H₅₁NSi₂
• Molecular Weight: 505.935
• Mol file: 248276-95-1.mol

Synonyms:N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline

Chemical Property of N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline

There total 6 articles about N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline 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: 89.0%

trimethylsilyl-1,3-butadiyne (4526-06-1) + N,N-dibutyl-4-iodo-3-[(triisopropylsilyl)ethynyl]aniline (248276-94-0) → N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline (248276-95-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 50 ℃;

DOI:10.1021/ja991749g

Reference yield: 80.0%

(Z)-(4-chloro-3-buten-1-ynyl)trimethylsilane (119951-16-5) + N,N-dibutyl-4-iodo-3-[(triisopropylsilyl)ethynyl]aniline (248276-94-0) → N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline (248276-95-1)

Guidance literature:

(Z)-(4-chloro-3-buten-1-ynyl)trimethylsilane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.0333333h;

With zinc dibromide; In tetrahydrofuran; at 0 ℃; for 0.25h;

N,N-dibutyl-4-iodo-3-[(triisopropylsilyl)ethynyl]aniline; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 48h; Heating;

DOI:10.1021/ol0345576

Reference yield:

tris-iso-propylsilyl acetylene (89343-06-6) → N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[4-(trimethylsilyl)-1,3-butadiynyl]aniline (248276-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 50 °C

2: 96 percent / BnNEt₃⁽¹⁺⁾*ICl₂^(1-); CaCO₃ / CH₂Cl₂; methanol / 2 h

3: 89 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 50 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; calcium carbonate; benzyl triethylammonium dichloroiodate; In methanol; dichloromethane; 1: Substitution / 2: Iodination / 3: Substitution;

DOI:10.1021/ja991749g

upstream raw materials:

trimethylsilyl-1,3-butadiyne

N,N-dibutyl-4-iodo-3-[(triisopropylsilyl)ethynyl]aniline

(Z)-(4-chloro-3-buten-1-ynyl)trimethylsilane

tris-iso-propylsilyl acetylene

Downstream raw materials:

Dibutyl-[5-(4-{4-dibutylamino-2-[(triisopropylsilanyl)-ethynyl]-phenyl}-buta-1,3-diynyl)-4-iodo-2-nitro-phenyl]-amine

C₅₈H₈₄N₂Si₂

Dibutyl-[5-(4-{4-dibutylamino-2-[(triisopropylsilanyl)-ethynyl]-phenyl}-buta-1,3-diynyl)-2-nitro-4-(4-{4-nitro-2-[(triisopropylsilanyl)-ethynyl]-phenyl}-buta-1,3-diynyl)-phenyl]-amine

C₁₂₂H₁₇₀N₄Si₄