3-[tert-Butyl(diphenyl)silyl]prop-2-yn-1-ol

Base Information

• Chemical Name: 3-[tert-Butyl(diphenyl)silyl]prop-2-yn-1-ol
• CAS No.: 126741-70-6
• Molecular Formula: C19H22OSi
• Molecular Weight: 294.469
• DSSTox Substance ID: DTXSID10561278
• Nikkaji Number: J2.795.245C
• Wikidata: Q82445007
• Mol file: 126741-70-6.mol

Synonyms:126741-70-6;3-[tert-Butyl(diphenyl)silyl]prop-2-yn-1-ol;SCHEMBL12482246;DTXSID10561278

Chemical Property of 3-[tert-Butyl(diphenyl)silyl]prop-2-yn-1-ol

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 294.143991855
• Heavy Atom Count: 21
• Complexity: 365

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#CCO)(C1=CC=CC=C1)C2=CC=CC=C2

Technology Process of 3-[tert-Butyl(diphenyl)silyl]prop-2-yn-1-ol

There total 6 articles about 3-[tert-Butyl(diphenyl)silyl]prop-2-yn-1-ol 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: 81.0%

tert-Butyl-diphenyl-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-silane → 1-<(1',1'-dimethylethyl)diphenylsilyl>prop-1-yn-3-ol (126741-70-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; Inert atmosphere; Reflux;

DOI:10.1002/chem.201501648

Reference yield: 74.0%

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-<(1',1'-dimethylethyl)diphenylsilyl>prop-1-yn-3-ol (126741-70-6)

Guidance literature:

3-(tetrahydropyran-2'-yloxy)propyne; With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.333333h;

tert-butylchlorodiphenylsilane; In tetrahydrofuran; hexane; at 0 - 20 ℃;

With toluene-4-sulfonic acid; In methanol; for 3h; Further stages.;

DOI:10.1021/ja011983i

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 1-<(1',1'-dimethylethyl)diphenylsilyl>prop-1-yn-3-ol (126741-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.58 h / -80 °C

1.2: tetrahydrofuran; hexane / 0.17 h / -80 - 20 °C

2.1: p-toluenesulfonic acid monohydrate / acetone; H₂O / 0.67 h / Heating

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; water; acetone;

DOI:10.1016/j.tetlet.2005.07.120

upstream raw materials:

formaldehyd

1-<(1',1'-dimethylethyl)diphenylsilyl>acetylene

3-(tetrahydropyran-2'-yloxy)propyne

tert-butylchlorodiphenylsilane

Downstream raw materials:

1-({[(3-(tert-butyldiphenylsilanyl)prop-2-ynyl)oxy]dithio}oxy)-3-(tert-butyldiphenylsilanyl)prop-2-yne

[(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxiranyl]-methanol

(2S,3S)-3-(tert-Butyl-diphenyl-silanyl)-oxirane-2-carbaldehyde

(1S,2S) 1-tert-butyldiphenylsilyl-1,2-epoxy-but-3-ene