4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene

Base Information

• Chemical Name: 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene
• CAS No.: 221292-53-1
• Molecular Formula: C₂₈H₃₈SSi₂
• Molecular Weight: 462.847
• Mol file: 221292-53-1.mol

Synonyms:4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene

Chemical Property of 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene

There total 11 articles about 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene 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: 77.4%

2-(trimethylsilyl)ethynyl-5-iodotoluene (207724-68-3) + 2-(tert-butyldimethylsilyl)ethyl-4'-(ethynyl)phenyl sulfide (221292-46-2) → 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene (221292-53-1)

Guidance literature:

With copper(l) iodide; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 60 ℃; for 2.5h;

DOI:10.1021/jo982392m

Reference yield:

meta-bromotoluene (591-17-3) → 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene (221292-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 53.8 percent / AlCl₃ / CH₂Cl₂ / Ambient temperature

2: 1.) LDA, diethyl chlorophosphate, 2.) LDA / 1.) THF, -78 deg C, 15 min, then room temp., 3 h, 2.) THF, room temp., overnight

3: 1.) t-BuLi, 2.) I₂ / 1.) ether, pentane, -78 deg C, 30 min, 2.) ether, pentane, 0 deg C, 10 min

4: 77.4 percent / Pd(dba)2, PPh₃, CuI, diisopropylamine / dimethylformamide / 2.5 h / 60 °C

With copper(l) iodide; aluminium trichloride; iodine; tert.-butyl lithium; diethyl chlorophosphate; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; lithium diisopropyl amide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo982392m

Reference yield:

3-Iodotoluene (625-95-6) → 4-{4-[2-(tert-Butyl-dimethyl-silanyl)-ethylsulfanyl]-phenylethynyl}-2-methyl-1-trimethylsilanylethynyl-benzene (221292-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 28.5 percent / AlCl₃ / 1,2-dichloro-ethane / 1.) room temp., 1 h, 2.) 50 deg C, 2 h

2: 1.) LDA, diethyl chlorophosphate, 2.) LDA / 1.) THF, -78 deg C, 15 min, then room temp., 3 h, 2.) THF, room temp., overnight

3: 77.4 percent / Pd(dba)2, PPh₃, CuI, diisopropylamine / dimethylformamide / 2.5 h / 60 °C

With copper(l) iodide; aluminium trichloride; diethyl chlorophosphate; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; lithium diisopropyl amide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo982392m

upstream raw materials:

2-(trimethylsilyl)ethynyl-5-iodotoluene

2-(tert-butyldimethylsilyl)ethyl-4'-(ethynyl)phenyl sulfide

meta-bromotoluene

3-Iodotoluene

Downstream raw materials:

tert-butyl-{2-[4-(4-ethynyl-3-methyl-phenylethynyl)-phenylsulfanyl]-ethyl}-dimethyl-silane

Refernces