4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline

Base Information

• Chemical Name: 4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline
• CAS No.: 1263305-89-0
• Molecular Formula: C₁₅H₁₄INS
• Molecular Weight: 367.253
• Mol file: 1263305-89-0.mol

Synonyms:4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline

Chemical Property of 4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline

There total 2 articles about 4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline 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: 77.0%

2,4-diiodo-5-methylthiophene (16494-38-5) + 4-ethynyl-N,N-dimethylaniline (17573-94-3,752235-18-0) → 4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline (1263305-89-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In diethyl ether; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.dyepig.2010.03.018

Reference yield:

2-Methylthiophene (554-14-3) → 4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline (1263305-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine; iodic acid; acetic acid / chloroform; water / 24 h / Reflux

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / diethyl ether / 20 h / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; iodic acid; acetic acid; diisopropylamine; In diethyl ether; chloroform; water; 2: Sonogashira coupling;

DOI:10.1016/j.dyepig.2010.03.018

Reference yield: 44.0%

4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline (1263305-89-0) + (5-chloro-2-methyl-3-thienyl)perfluorocyclopentene (499204-88-5) → 1-(5-chloro-2-methyl-3-thienyl)-2-(2-methyl-5-[4-ethenyl-N,N-dimethylaniline]-3-thienyl)perfluorocyclopentene (1263306-06-4)

Guidance literature:

4-[(4-iodo-5-methylthiophen-2-yl)ethynyl]-N,N-dimethylaniline; With n-butyllithium; In diethyl ether; hexane; at -80 ℃; for 1h; Inert atmosphere;

(5-chloro-2-methyl-3-thienyl)perfluorocyclopentene; In diethyl ether; hexane; at -80 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1016/j.dyepig.2010.03.018

upstream raw materials:

2-Methylthiophene

2,4-diiodo-5-methylthiophene

4-ethynyl-N,N-dimethylaniline

Downstream raw materials:

1-(5-chloro-2-methyl-3-thienyl)-2-(2-methyl-5-[4-ethenyl-N,N-dimethylaniline]-3-thienyl)perfluorocyclopentene

1-(5-formyl-2-methyl-3-thienyl)-2-(2-methyl-5-[4-ethenyl-N,N-dimethylaniline]-3-thienyl)perfluorocyclopentene