Silane, trimethyl[[4-[[2-(trimethylsilyl)ethyl]thio]phenyl]ethynyl]-

Base Information

• Chemical Name: Silane, trimethyl[[4-[[2-(trimethylsilyl)ethyl]thio]phenyl]ethynyl]-
• CAS No.: 221292-43-9
• Molecular Formula: C16H26SSi2
• Molecular Weight: 306.619
• DSSTox Substance ID: DTXSID00441878
• Wikidata: Q82258871
• Mol file: 221292-43-9.mol

Synonyms:221292-43-9;Silane, trimethyl[[4-[[2-(trimethylsilyl)ethyl]thio]phenyl]ethynyl]-;DTXSID00441878

Chemical Property of Silane, trimethyl[[4-[[2-(trimethylsilyl)ethyl]thio]phenyl]ethynyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 306.12937507
• Heavy Atom Count: 19
• Complexity: 329

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CCSC1=CC=C(C=C1)C#C[Si](C)(C)C

Technology Process of Silane, trimethyl[[4-[[2-(trimethylsilyl)ethyl]thio]phenyl]ethynyl]-

There total 4 articles about Silane, trimethyl[[4-[[2-(trimethylsilyl)ethyl]thio]phenyl]ethynyl]- 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: 95.0%

4-iodo-1-[2-(trimethylsilyl)ethylsulfanyl]benzene (221292-41-7) + trimethylsilylacetylene (1066-54-2) → 2-(trimethylsilyl)ethyl-4'-<(trimethylsilyl)ethynyl>phenyl sulfide (221292-43-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; at 50 ℃; for 1.5h;

DOI:10.1021/jo982392m

Reference yield:

1-[(4-bromophenyl)sulfanyl]-2-(trimethylsilyl)ethane (221292-39-3) + trimethylsilylacetylene (1066-54-2) → 2-(trimethylsilyl)ethyl-4'-<(trimethylsilyl)ethynyl>phenyl sulfide (221292-43-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; at 60 ℃; for 18h; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.201900432

Reference yield:

ethenyltrimethylsilane (754-05-2) → 2-(trimethylsilyl)ethyl-4'-<(trimethylsilyl)ethynyl>phenyl sulfide (221292-43-9)

Guidance literature:

Multi-step reaction with 2 steps

1: di-tert-butyl peroxide / 5.5 h / 100 °C / Microwave irradiation

2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine / 18 h / 60 °C / Schlenk technique; Sealed tube

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; di-tert-butyl peroxide; diethylamine; 2: |Sonogashira Cross-Coupling;

DOI:10.1002/ejoc.201900432

upstream raw materials:

4-iodo-1-[2-(trimethylsilyl)ethylsulfanyl]benzene

trimethylsilylacetylene

ethenyltrimethylsilane

1-[(4-bromophenyl)sulfanyl]-2-(trimethylsilyl)ethane

Downstream raw materials:

2-Methyl-4-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenylethynyl]-1-trimethylsilanylethynyl-benzene

2-(trimethylsilyl)ethyl-4’-ethynylphenyl sulfide