2-(But-3-yn-1-yl)phenol

Base Information

• Chemical Name: 2-(But-3-yn-1-yl)phenol
• CAS No.: 139704-04-4
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• DSSTox Substance ID: DTXSID00566055
• Nikkaji Number: J470.011B
• Wikidata: Q82451491
• Mol file: 139704-04-4.mol

Synonyms:2-(But-3-yn-1-yl)phenol;139704-04-4;DTXSID00566055;EN300-1826951

Chemical Property of 2-(But-3-yn-1-yl)phenol

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCC1=CC=CC=C1O

Technology Process of 2-(But-3-yn-1-yl)phenol

There total 4 articles about 2-(But-3-yn-1-yl)phenol 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: 74.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + 3-(2-((tertbutyldimethylsilyl)oxy)phenyl)propanal (783333-07-3) → 4-(2-hydroxyphenyl)-1-butyne (139704-04-4)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1021/ja048078t

Reference yield: 68.0%

2-(1-hydroxybut-3-yn-1-yl)phenol → 4-(2-hydroxyphenyl)-1-butyne (139704-04-4)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at -40 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03586

Reference yield:

3-(2-((tert-butyldimethylsilyl)oxy)phenyl)propan-1-ol (327155-45-3) → 4-(2-hydroxyphenyl)-1-butyne (139704-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 74 percent / K₂CO₃ / methanol / 20 °C

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; 1: Swern oxidation;

DOI:10.1021/ja048078t

upstream raw materials:

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

3-(2-((tertbutyldimethylsilyl)oxy)phenyl)propanal

3-(2-((tert-butyldimethylsilyl)oxy)phenyl)propan-1-ol

salicylaldehyde

Downstream raw materials:

2-[1-Phenyl-meth-(E)-ylidene]-chroman

2-(2-(benzofuran-2-yl)ethyl)phenol

2,2'-spirobi[chroman]-4-one

2-(2-hydroxyphenethyl)-4H-chromen-4-one