tert-Butyl(4-ethynylphenoxy)dimethylsilane

Base Information

• Chemical Name: tert-Butyl(4-ethynylphenoxy)dimethylsilane
• CAS No.: 136053-34-4
• Molecular Formula: C14H20OSi
• Molecular Weight: 232.398
• European Community (EC) Number: 877-869-5
• Nikkaji Number: J1.264.492B
• Mol file: 136053-34-4.mol

Synonyms:tert-Butyl(4-ethynylphenoxy)dimethylsilane;136053-34-4;tert-butyl-(4-ethynylphenoxy)-dimethylsilane;ICCB6_000083;CBiol_000975;SCHEMBL9051730;ICCB4_000271;4-Ethynylphenoxy-tert-butyldimethylsilane;BCB03_000047;BS-30741;F84536;tert-Butyl-(4-ethynyl-phenoxy)-dimethyl-silane;EN300-7406471;A1-02142

Chemical Property of tert-Butyl(4-ethynylphenoxy)dimethylsilane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 232.128341792
• Heavy Atom Count: 16
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1=CC=C(C=C1)C#C

Technology Process of tert-Butyl(4-ethynylphenoxy)dimethylsilane

There total 13 articles about tert-Butyl(4-ethynylphenoxy)dimethylsilane 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: 100.0%

4-ethynylphenol (2200-91-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-[(tert-butyldimethylsilyl)oxy]-4-ethynylbenzene (136053-34-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/anie.200603659

Reference yield: 97.0%

[{4-(1,1-dimethylethyl)dimethylsiloxyphenyl}ethynyl]trimethylsilane (200625-51-0) → 1-[(tert-butyldimethylsilyl)oxy]-4-ethynylbenzene (136053-34-4)

Guidance literature:

With silver nitrate; In pyridine; water; acetone; at 40 ℃; for 33h;

DOI:10.1002/ejoc.200400810

Reference yield: 91.0%

tert-butyl(4-(2,2-dibromoethenyl)phenoxy)dimethylsilane (347377-08-6) → 1-[(tert-butyldimethylsilyl)oxy]-4-ethynylbenzene (136053-34-4)

Guidance literature:

tert-butyl(4-(2,2-dibromoethenyl)phenoxy)dimethylsilane; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 2h;

With ammonium chloride; In tetrahydrofuran; n-heptane; ethylbenzene;

DOI:10.1016/j.ejmech.2011.03.022

upstream raw materials:

t-butyldimethylsilyl-4-bromophenol

sodium acetylide

4-(tert-butyldimethylsilyloxy)iodobenzene

[{4-(1,1-dimethylethyl)dimethylsiloxyphenyl}ethynyl]trimethylsilane

Downstream raw materials:

3-(4-tert-butyldimethylsilyloxyphenyl)propiolic acid

(R)-1-[(4-(tert-butyldimethylsiloxy)phenyl)ethynyl]-2-[(1-phenylethyl)thio]benzene

2-{6-[4-(tert-butyldimethylsilanyloxy)phenyl]-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl}-propan-2-ol

(R)-(-)-2-{6-[4-(tert-butyldimethylsilanyloxy)phenyl]-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl}-propan-2-ol

Refernces

• 1、 Angelici, Gaetano,Carpita, Adriano,Casotti, Gianluca,Evangelisti, Claudio,Ferreri, Matteo,Fusini, Graziano,Pardini, Luca Fidia. "Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts". . p. 1795 - 1803. Retrieved 2020/06/08.
• 2、 Pennell, Matthew N.,Turner, Peter G.,Sheppard, Tom D.. "Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives". experimental part. p. 4748 - 4758. Retrieved 2012/05/04.