3-COUMARANONE

Base Information

• Chemical Name: 3-COUMARANONE
• CAS No.: 7169-34-8
• Molecular Formula: C8H6O2
• Molecular Weight: 134.134
• Hs Code.: 29329990
• European Community (EC) Number: 640-279-1
• NSC Number: 512726
• UNII: KZ7LS8K9LP
• DSSTox Substance ID: DTXSID20221917
• Nikkaji Number: J20.648B
• Wikidata: Q72445530
• ChEMBL ID: CHEMBL2253270
• Mol file: 7169-34-8.mol

Synonyms:1-Benzofuran-3(2H)-one;2,3-Dihydro-1-benzofuran-3-one;2,3-Dihydro-3-oxobenzofuran;2,3-Dihydrobenzofuran-3-one;Benzo[b]furan-3(2H)-one;Benzofran-3-one;Benzofuran-3(2H)-one;Coumaran-3-one;Coumaranone;NSC 512726;b-Coumaranone;

Chemical Property of 3-COUMARANONE

Chemical Property:

• Appearance/Colour: white to light yellow crystal powde
• Vapor Pressure: 0.023mmHg at 25°C
• Melting Point: 101-103 °C
• Refractive Index: 1.585
• Boiling Point: 249.643 °C at 760 mmHg
• Flash Point: 118.944 °C
• PSA: 26.30000
• Density: 1.265 g/cm³
• LogP: 1.26170
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility.: Slightly miscible with water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.036779430
• Heavy Atom Count: 10
• Complexity: 153

Purity/Quality:

99%, ^*data from raw suppliers

3-Coumaranone >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)C2=CC=CC=C2O1
• General Description: 3-COUMARANONE is a flavonoid derivative that was investigated as part of a broader study on anti-HIV agents, where it was screened alongside chalcones and other flavonoids for inhibitory activity against HIV-1. While the study highlighted O-benzyl-substituted chalcones as particularly effective, the specific anti-HIV performance of 3-COUMARANONE itself was not detailed in the provided abstract. Therefore, no conclusive findings regarding its bioactivity or cytotoxicity can be drawn from this literature.

Technology Process of 3-COUMARANONE

There total 15 articles about 3-COUMARANONE 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: 92.2%

2-ethynyl-phenol (5101-44-0) → 3-oxo-2,3-dihydrobenzo[b]furan (7169-34-8)

Guidance literature:

With 2-chloropyridine-N-oxide; mercuric triflate; In dichloromethane; at 23 ℃; for 1h; Reagent/catalyst; Catalytic behavior;

DOI:10.1021/acs.orglett.0c01096

Reference yield: 86.0%

1-ethynyl-2-methoxybenzene (767-91-9) → 3-oxo-2,3-dihydrobenzo[b]furan (7169-34-8)

Guidance literature:

With methanesulfonic acid; 8-isopropyl-quinoline-N-oxide; (2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)Au(1H-benzotriazole)NTf₂; In 1,2-dichloro-ethane; at 20 ℃; for 5h; Reagent/catalyst;

DOI:10.1002/asia.201403032

Reference yield: 43.0%

(E)-2'-hydroxychalcone epoxide (129878-47-3) → 3-oxo-2,3-dihydrobenzo[b]furan (7169-34-8) + 3-hydroxyflavone (577-85-5,66585-05-5) + rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + rac-trans-3-hydroxyflavanone (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + threo-2-(α-hydroxybenzyl)-3-coumaranone (14796-31-7) + erythro-2-(α-hydroxybenzyl)-3-coumaranone

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.0333333h; Product distribution; Mechanism; other sucstituted 2'-hydroxychalcones, other reagents: triethylamine, 4-(dimethylamino)pyridine, tetrabutylammonium hydroxide, HCl, HClO₄, other solvents: ethanol/water, water, CH₂Cl₂/water, other temperature and reaction time;

DOI:10.1021/jo960163z

upstream raw materials:

Phenoxyacetyl chloride

2.3-dihydrobenzofuran

(2-hydroxy-phenyl)-(3-phenyl-oxiranyl)-methanone

phosphoric acid dibenzyl ester

Downstream raw materials:

3-methyl-benzofuran

3-ethylbenzo[b]furan

(Z)-2-(4-nitrobenzylidene)benzofuran-3(2H)-one

3-Phenylbenzofuran

Refernces

Synthesis and bioevaluation of substituted chalcones, coumaranones and other flavonoids as anti-HIV agents

10.1016/j.bmc.2016.04.045

The research aimed to identify and develop novel anti-HIV compounds from the class of flavonoids, specifically focusing on chalcones, coumaranones, and other flavonoid derivatives. The purpose was to screen these compounds for their anti-HIV-1 activity and to evaluate their potency and cytotoxicity in two cell culture models, TZM-bl and PM1 cells. The study concluded that O-benzyl-substituted chalcones, particularly chalcones 8o and 8p, showed promise as anti-HIV agents due to their high anti-viral potency and low cytotoxicity. These compounds significantly inhibited HIV propagation at low micromolar doses and were relatively non-toxic to the cell lines tested. The chemicals used in the process included a series of chalcone, flavone, coumaranone, and other flavonoid compounds, with specific focus on those containing an α- or β-hydroxy-carbonyl motif within their structure, such as chalcone 8l, flavonol 9c, and the newly designed chalcones 8o and 8p.

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