7-Hydroxy-5-methylcoumarin

Base Information

• Chemical Name: 7-Hydroxy-5-methylcoumarin
• CAS No.: 7249-26-5
• Molecular Formula: C10H8 O3
• Molecular Weight: 176.1687
• European Community (EC) Number: 835-411-1
• NSC Number: 42243
• DSSTox Substance ID: DTXSID80418003
• Wikidata: Q82228269
• ChEMBL ID: CHEMBL457963
• Mol file: 7249-26-5.mol

Synonyms:5-methylumbelliferone;7-hydroxy-5-methylcoumarin;7249-26-5;7-hydroxy-5-methylchromen-2-one;2H-1-Benzopyran-2-one, 7-hydroxy-5-methyl-;NSC42243;7-hydroxy-5-methyl-2H-chromen-2-one;5-methyl-7-hydroxycoumarin;7-hydroxy-5-methyl-coumarin;CHEMBL457963;SCHEMBL6703952;DTXSID80418003;QNDMQTVAGWUUDS-UHFFFAOYSA-N;MFCD00488356;NSC-42243;M2948;T72881

Chemical Property of 7-Hydroxy-5-methylcoumarin

Chemical Property:

• Vapor Pressure: 9.1E-07mmHg at 25°C
• Boiling Point: 393.9°Cat760mmHg
• Flash Point: 183.1°C
• Density: 1.336g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 176.047344113
• Heavy Atom Count: 13
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC2=C1C=CC(=O)O2)O

Technology Process of 7-Hydroxy-5-methylcoumarin

There total 15 articles about 7-Hydroxy-5-methylcoumarin 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: 93.0%

orcinol (504-15-4) + Propiolic acid (471-25-0) → 7-hydroxy-5-methyl-chromen-2-one (7249-26-5)

Guidance literature:

With ytterbium(III) trifluoromethanesulfonate hydrate; at 80 ℃; for 0.0333333h; Reagent/catalyst; Microwave irradiation;

DOI:10.1016/j.tetlet.2016.05.087

Reference yield: 85.0%

orcinol (504-15-4) + malic acid (617-48-1,78644-42-5) → 7-hydroxy-5-methyl-chromen-2-one (7249-26-5)

Guidance literature:

With sulfuric acid; for 0.0541667h; Microwave irradiation;

DOI:10.1016/j.bmcl.2008.12.098

Reference yield: 70.0%

orcinol (504-15-4) + ethyl 3,3-diethoxypropanoate (10601-80-6) → 7-hydroxy-5-methyl-chromen-2-one (7249-26-5)

Guidance literature:

orcinol; ethyl 3,3-diethoxypropanoate; at 120 ℃;

With sulfuric acid; trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1021/jm049535j

upstream raw materials:

orcinol

malic acid

5-methyl-7-acetoxycoumarin

7-hydroxy-5-methyl-2-oxo-2H-chromene-3-carboxylic acid

Downstream raw materials:

C₁₇H₁₂O₄

5,5'-dimethylangelicin

5-methylangelicin

5-(bromomethyl)-7-methoxy-2H-chromen-2-one

Refernces

• 1、 Fiorito, Serena,Epifano, Francesco,Taddeo, Vito A.,Genovese, Salvatore. "Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins". supporting information. p. 2939 - 2942. Retrieved 2016/06/14.
• 2、 Timonen, Juri M.,Nieminen, Riina M.,Sareila, Outi,Goulas, Antonis,Moilanen, Lauri J.,Haukka, Matti,Vainiotalo, Pirjo,Moilanen, Eeva,Aulaskari, Paula H.. "Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives". supporting information; experimental part. p. 3845 - 3850. Retrieved 2011/11/13.