4-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one

Base Information

• Chemical Name: 4-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one
• CAS No.: 81535-84-4
• Molecular Formula: C16H22O2Si
• Molecular Weight: 274.435
• DSSTox Substance ID: DTXSID60446561
• Nikkaji Number: J1.814.574J
• Wikidata: Q82265257

Synonyms:4-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one;81535-84-4;SCHEMBL974627;DTXSID60446561;KWINCCGVOOJRKI-UHFFFAOYSA-N;1-Phenyl-4-(tert-butyldimethylsiloxy)-2-butyne-1-one;4-(tert-butyldimethylsilyloxy)-1-phenylbut-2-yn-1-one

Chemical Property of 4-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 274.138906475
• Heavy Atom Count: 19
• Complexity: 373

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one

There total 5 articles about 4-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one 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: 99.0%

N-methoxy-N-methylbenzamide (6919-61-5) + tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → 4-<(tert-butyldimethylsilyl)oxy>-1-phenyl-2-butyn-1-one (81535-84-4)

Guidance literature:

tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; In tetrahydrofuran; at -78 - -30 ℃; for 0.5h;

N-methoxy-N-methylbenzamide; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield: 94.0%

tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) + benzoyl chloride (98-88-4) → 4-<(tert-butyldimethylsilyl)oxy>-1-phenyl-2-butyn-1-one (81535-84-4)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 0.666667h;

DOI:10.1039/b414826f

Reference yield: 78.0%

benzoyl chloride (98-88-4) + C18H38BO4Si(1-)*Li(1+) → 4-<(tert-butyldimethylsilyl)oxy>-1-phenyl-2-butyn-1-one (81535-84-4)

Guidance literature:

With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 60 ℃; for 8h;

DOI:10.1016/j.tetlet.2004.09.114

upstream raw materials:

tert-butyl-dimethyl(3-(tributylstannanyl)prop-2-yn-1-yl)oxysilane

benzoyl chloride

[4-(tert-Butyl-dimethyl-silanyloxy)-1-trimethylsilanyloxy-but-2-ynyl]-benzene

N-methoxy-N-methylbenzamide

Downstream raw materials:

C₁₉H₃₀O₂S₂Si

C₁₈H₂₈O₂S₂Si

(E)-4-(tert-butyldimethylsilyl)oxy-2-dimethyl(phenyl)silyl-1-phenyl-2-buten-1-one

4-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylbutan-1-one

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