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:

98%,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
• Uses: 3-Coumaranone is used in the aurones, [2-benzylidenebenzofuran-3(2H)-ones] by reacting with appropriate aldehyde. It is involved in the condensation reaction with aldehydes in the presence of morpholine acetate to prepare substituted 2-(arylidene)benzofuran-3(ZH)-ones. In Horner-Wadsworth-Emmons reaction, it reacts with diethyl? cyanomethyl?phosphonate to give 3-(cyanomethyl)benzofurans, which is an intermediate in the synthesis of antihyperglycemic agents.

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

• 1、 -. "Catalytic synthesis method of 3-benzofuranone compound". Paragraph 0014-0017. . Retrieved 2020/05/14.
• 2、 Shu, Chao,Liu, Rongfu,Liu, Shuang,Li, Jian-Qiao,Yu, Yong-Fei,He, Qiao,Lu, Xin,Ye, Long-Wu. "Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy". supporting information. p. 91 - 95. Retrieved 2015/02/19.