5 7-DIHYDROXY-4-PHENYLCOUMARIN

Base Information

• Chemical Name: 5 7-DIHYDROXY-4-PHENYLCOUMARIN
• CAS No.: 7758-73-8
• Molecular Formula: C15H10O4
• Molecular Weight: 254.242
• Hs Code.: 2932209090
• European Community (EC) Number: 622-107-7
• DSSTox Substance ID: DTXSID90228251
• Nikkaji Number: J412.126K
• Wikidata: Q72466897
• Metabolomics Workbench ID: 23034
• ChEMBL ID: CHEMBL600635
• Mol file: 7758-73-8.mol

Synonyms:Coumarin,5,7-dihydroxy-4-phenyl- (6CI,7CI,8CI);5,7-Dihydroxy-4-phenylcoumarin;5,7-Dihydroxy-4-phenyl-2H-1-benzopyran-2-one;

Chemical Property of 5 7-DIHYDROXY-4-PHENYLCOUMARIN

Chemical Property:

• Vapor Pressure: 4.42E-12mmHg at 25°C
• Melting Point: 227-233 °C(lit.)
• Refractive Index: 1.698
• Boiling Point: 535.5 °C at 760 mmHg
• Flash Point: 210.5 °C
• PSA: 70.67000
• Density: 1.443 g/cm³
• LogP: 2.87120
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.05790880
• Heavy Atom Count: 19
• Complexity: 384

Purity/Quality:

98%,99%, ^*data from raw suppliers

5,7-Dihydroxy-4-phenylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)OC3=CC(=CC(=C23)O)O

Technology Process of 5 7-DIHYDROXY-4-PHENYLCOUMARIN

There total 22 articles about 5 7-DIHYDROXY-4-PHENYLCOUMARIN 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: 96.0%

3,5-dihydroxyphenol (108-73-6) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → 5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one (7758-73-8)

Guidance literature:

With ammonium cerium(IV) nitrate; silica gel; for 0.05h; microwave irradiation;

DOI:10.1080/00397910802029091

Reference yield: 95.0%

3,5-dihydroxyphenol (108-73-6) + phenylpropynoic acid ethyl ester (2216-94-6) → 5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one (7758-73-8)

Guidance literature:

With zinc(II) chloride; at 100 ℃; for 0.0833333h; neat (no solvent);

DOI:10.1055/s-0031-1289576

Reference yield: 90.0%

phenyl acetoacetate (6864-62-6) + 3,5-dihydroxyphenol (108-73-6) → 5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one (7758-73-8)

Guidance literature:

With polystyrene supported GaCl₃; In ethanol; for 1.16667h; Reflux; Green chemistry;

DOI:10.1016/j.crci.2013.01.006

upstream raw materials:

3,5-dihydroxyphenol

3-amino-3-phenylacrylonitrile

5,7-dimethoxy-4-phenyl-chromen-2-one

5-acetoxy-7-methoxy-4-phenyl-coumarin

Downstream raw materials:

6-allyl-5,7-dihydroxy-4-phenyl-2H-chromen-2-one

5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one

5,7-dihydroxy-8-(2-methyl-1-oxobutyl)-4-phenyl-2H-[1]benzopyran-2-one

6-benzoyl-5,7-dihydroxy-4-phenyl-2H-chromen-2-one

Refernces

• 1、 Kumar, Ajit,Singh, Brajendra K.,Tyagi, Rahul,Jain, Sapan K.,Sharma, Sunil K.,Prasad, Ashok K.,Raj, Hanumantharao G.,Rastogi, Ramesh C.,Watterson, Arthur C.,Parmar, Virinder S.. "Mechanism of biochemical action of substituted 4-methylcoumarins. Part 11: Comparison of the specificities of acetoxy derivatives of 4-methylcoumarin and 4-phenylcoumarin to acetoxycoumarins: Protein transacetylase". . p. 4300 - 4305. Retrieved 2005.
• 2、 Barcellos, Thiago,Lenard?o, Eder J.,Moraes, Maiara C.. "Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis". . p. 151 - 163. Retrieved 2022/01/28.
• 3、 Bahramnezhad, Baharak,Ghazanfari, Dadkhoda,Sheikhhosseini, Enayatollah,Akhgar, Mohammad Reza,Ahmadi, Sayed Ali. "MnSb2O6-chitosan nanocomposite: An efficient catalyst for the synthesis of coumarins via Pechmann reaction". supporting information. p. 173 - 181. Retrieved 2019/11/20.