2-(2-Heptynylthio)phenol Acetate

Base Information

• Chemical Name: 2-(2-Heptynylthio)phenol Acetate
• CAS No.: 209125-28-0
• Molecular Formula: C₁₅H₁₈O₂S
• Molecular Weight: 262.373
• UNII: GNC4EUY582
• DSSTox Substance ID: DTXSID40175069
• Nikkaji Number: J965.867J
• Wikidata: Q83045307
• Pharos Ligand ID: 1KY1JKMLHLQZ
• ChEMBL ID: CHEMBL345018
• Mol file: 209125-28-0.mol

Synonyms:APHS;N'-(3-aminopropyl)homospermidine

Chemical Property of 2-(2-Heptynylthio)phenol Acetate

Chemical Property:

• Vapor Pressure: 1.82E-05mmHg at 25°C
• Boiling Point: 363.3°Cat760mmHg
• Flash Point: 165.7°C
• PSA: 51.60000
• Density: 1.1g/cm³
• LogP: 3.51880
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 262.10275099
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

97% ^*data from raw suppliers

2-(2-Heptynylthio)phenolAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC#CCSC1=CC=CC=C1OC(=O)C
• Uses: An O-acetyl, S-alkyl thio ether of 2-thio phenol. It is a potent inhibitor of both COX-1 and COX-2, with IC50 values of 17 and 0.8uM for human recombinant COX-1 and COX-2 respectively. APHS exhibits 20-fold selectivity toward the inhibition of COX-2, yet it is still more potent than aspirin in the inhibition of COX-1.

Technology Process of 2-(2-Heptynylthio)phenol Acetate

There total 3 articles about 2-(2-Heptynylthio)phenol Acetate 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: 92.0%

acetic anhydride (108-24-7) + 2-hydroxyphenyl hept-2-ynyl sulfide (210350-98-4) → o-(acetoxy)phenyl hept-2-ynyl sulfide (209125-28-0)

Guidance literature:

With pyridine; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1021/jm980303s

Reference yield:

1-bromo-2-heptyne (18495-26-6) → o-(acetoxy)phenyl hept-2-ynyl sulfide (209125-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / KHCO₃ / dimethylformamide / Ambient temperature

2: 92 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; potassium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980303s

Reference yield:

hep-2-yn-1-ol (1002-36-4) → o-(acetoxy)phenyl hept-2-ynyl sulfide (209125-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / CBr₄, Ph₃P, pyridine / tetrahydrofuran / 4 h / Ambient temperature

2: 71 percent / KHCO₃ / dimethylformamide / Ambient temperature

3: 92 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; carbon tetrabromide; potassium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980303s

upstream raw materials:

acetic anhydride

2-hydroxyphenyl hept-2-ynyl sulfide

hep-2-yn-1-ol

1-bromo-2-heptyne

Refernces