7-ethynylcoumarin

Base Information

• Chemical Name: 7-ethynylcoumarin
• CAS No.: 270088-04-5
• Molecular Formula: C₁₁H₆O₂
• Molecular Weight: 170.167
• Mol file: 270088-04-5.mol

Synonyms:

Chemical Property of 7-ethynylcoumarin

Chemical Property:

• Melting Point: 132.0 to 136.0 °C
• Boiling Point: 321.9±37.0 °C(Predicted)
• Density: 1.26±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

7-Ethynylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 7-Ethynylcoumarin is a selective inhibitors of human cytochrome P450s 1A1 and 1A2.

Technology Process of 7-ethynylcoumarin

There total 4 articles about 7-ethynylcoumarin 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: 97.0%

7-((trimethylsilyl)ethynyl)-2H-chromen-2-one → 7-ethynyl-2H-chromen-2-one (270088-04-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In methanol; at 60 ℃; for 0.25h;

DOI:10.1021/tx990195s

Reference yield:

2-oxo-2H-benzopyran-7-yl trifluoromethanesulfonate (108530-10-5) → 7-ethynyl-2H-chromen-2-one (270088-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / palladium(II) acetate; PPh₃ / pyridine / 5 h / Heating

2: 97 percent / tetrabutylammonium fluoride / methanol / 0.25 h / 60 °C

With tetrabutyl ammonium fluoride; triethylamine; palladium diacetate; triphenylphosphine; In pyridine; methanol;

DOI:10.1021/tx990195s

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → 7-ethynyl-2H-chromen-2-one (270088-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridine / 4 h / ice cooling

2: 90 percent / Et₃N / palladium(II) acetate; PPh₃ / pyridine / 5 h / Heating

3: 97 percent / tetrabutylammonium fluoride / methanol / 0.25 h / 60 °C

With pyridine; tetrabutyl ammonium fluoride; triethylamine; palladium diacetate; triphenylphosphine; In pyridine; methanol;

DOI:10.1021/tx990195s

upstream raw materials:

7-hydroxy-2H-chromen-2-one

2-oxo-2H-benzopyran-7-yl trifluoromethanesulfonate

Downstream raw materials:

7-(1-(3-(bis((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amino)propyl)-1H-1,2,3-triazol-4-yl)-2H-chromen-2-one

Refernces

• 1、 Singh, Dileep Kumar,Nath, Mahendra. "Meso-Phenyl-triazole bridged porphyrin-coumarin dyads: Synthesis, characterization and photophysical properties". . p. 256 - 264. Retrieved 2015/06/16.
• 2、 Chtchigrovsky, Melanie,Primo, Ana,Gonzalez, Philippe,Molvinger, Karine,Robitzer, Mike,Quignard, Francoise,Taran, Frederic. "Functionalized chitosan as a green, recyclable, biopolymer-supported catalyst for the [3+2] huisgen cycloaddition". supporting information; experimental part. p. 5916 - 5920. Retrieved 2009/12/08.