5,7-Dihydroxycoumarin

Base Information

• Chemical Name: 5,7-Dihydroxycoumarin
• CAS No.: 2732-18-5
• Molecular Formula: C9H6O4
• Molecular Weight: 178.144
• Hs Code.: 2932209090
• NSC Number: 108415
• DSSTox Substance ID: DTXSID80181765
• Nikkaji Number: J80.553J
• Wikidata: Q72466569
• Metabolomics Workbench ID: 123634
• ChEMBL ID: CHEMBL156000
• Mol file: 2732-18-5.mol

Synonyms:5,7-dihydroxy-2H-chromen-2-one;5,7-Dihydroxycoumarin;2732-18-5;5,7-dihydroxychromen-2-one;2H-1-Benzopyran-2-one, 5,7-dihydroxy-;MFCD00488354;NSC108415;5,7-Dihydroxy-2H-1-benzopyran-2-one;5,7-dihydroxy-coumarin;Coumarin derivative, 1a;5,7-Dihydroxy-chromen-2-one;CHEMBL156000;SCHEMBL1860857;BDBM93216;DTXSID80181765;KIQQFVJHWNCGAU-UHFFFAOYSA-N;AKOS006228057;DS-1820;HY-W072009;NSC 108415;NSC-108415;AC-26503;PD158402;SY033827;AM20040069;CS-0103308;FT-0659181;EN300-7361732;A819014;5,7-Dihydroxy-2H-chromen-2-one;InChI=1/C9H6O4/c10-5-3-7(11)6-1-2-9(12)13-8(6)4-5/h1-4,10-11

Chemical Property of 5,7-Dihydroxycoumarin

Chemical Property:

• Vapor Pressure: 7.06E-11mmHg at 25°C
• Melting Point: 280 °C
• Refractive Index: 1.689
• Boiling Point: 506.402 °C at 760 mmHg
• PKA: 7.18±0.20(Predicted)
• Flash Point: 216.911 °C
• PSA: 70.67000
• Density: 1.563 g/cm³
• LogP: 1.20420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 178.02660867
• Heavy Atom Count: 13
• Complexity: 248

Purity/Quality:

98%min ^*data from raw suppliers

5,7-Dihydroxy-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)OC2=CC(=CC(=C21)O)O
• Uses: 5,7-Dihydroxy-2H-chromen-2-one can be used to prepare UV-?responsive coumarin controlled release and self-?repairing antifouling paint.

Technology Process of 5,7-Dihydroxycoumarin

There total 12 articles about 5,7-Dihydroxycoumarin 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: 98.0%

3,5-dihydroxyphenol (108-73-6) + Propiolic acid (471-25-0) → 5,7-dihydroxy-2H-chromen-2-one (2732-18-5)

Guidance literature:

Dowex 50x2-200; at 80 ℃; for 0.183333h; microwave irradiation (30 W);

DOI:10.1055/s-1999-2674

Reference yield: 90.0%

3,5-dihydroxyphenol (108-73-6) + propynoic acid ethyl ester (623-47-2) → 5,7-dihydroxy-2H-chromen-2-one (2732-18-5)

Guidance literature:

With zinc(II) chloride; at 100 ℃; for 2h;

DOI:10.1021/np0497447

Reference yield: 83.0%

3,5-dihydroxyphenol (108-73-6) + Propiolic acid (471-25-0) → 5,7-dihydroxy-2H-chromen-2-one (2732-18-5) + 8-(1-(5,7-dihydroxy-2-oxo-2H-chromen-3-yl)ethyl)-5,7-dihydroxy-2H-chromen-2-one (1447758-10-2)

Guidance literature:

In water; for 24h; Reagent/catalyst; Solvent; Temperature; Time; Reflux;

DOI:10.1021/ol401581p

upstream raw materials:

5,7-diacetoxyl-2-chromenone

3,5-dihydroxyphenol

diethyl 2-ethoxymethylenemalonate

6-(C-β-D-glucosyl)-5,7-dihydroxycoumarin

Downstream raw materials:

Limettin

5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one

4-methyl-5,7-dihydroxycoumarin

3,5-dihydroxyphenol

Refernces

• 1、 Vdovin, A. D.,Batsuren, D.,Batirov, E. Kh.,Yagudaev, M. R.,Malikov, V. M.. "1H AND 13C NMR SPECTRA AND THE STRUCTURE OF A NEW COUMARIN, C-GLYCOSIDE DAUROSIDE D, FROM Haplophyllum dauricum". . p. 413 - 416. Retrieved 1983.
• 2、 De La Hoz, Antonio,Moreno, Andrés,Vázquez, Ester. "Use of microwave irradiation and solid acid catalysts in an enhanced and environmentally friendly synthesis of coumarin derivatives". . p. 608 - 610. Retrieved 1999.
• 3、 Huang, Huidan,Chen, Jianqiu,Ren, Jie,Zhang, Chaofeng,Ji, Fei. "Palladium(II)-catalyzed efficient synthesis of wedelolactone and evaluation as potential tyrosinase inhibitor". . . Retrieved 2019/11/28.
• 4、 Huang, Zhongyan,Matsubara, Okiya,Jia, Shichong,Tokunaga, Etsuko,Shibata, Norio. "Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System". supporting information. p. 934 - 937. Retrieved 2017/02/26.