6-Methoxycoumarin

Base Information

• Chemical Name: 6-Methoxycoumarin
• CAS No.: 17372-53-1
• Molecular Formula: C10H8O3
• Molecular Weight: 176.172
• Hs Code.: 2932209090
• European Community (EC) Number: 890-050-7
• ChEMBL ID: CHEMBL496547
• DSSTox Substance ID: DTXSID00459751
• Metabolomics Workbench ID: 139180
• Nikkaji Number: J494.164K
• Wikidata: Q82283590
• Mol file: 17372-53-1.mol

Synonyms:6-methoxycoumarin;6-methoxy-2H-chromen-2-one;17372-53-1;6-methoxychromen-2-one;MFCD00016707;CHEMBL496547;SCHEMBL1108372;DTXSID00459751;CHEBI:178005;VKVCJIMMVPXDQD-UHFFFAOYSA-N;2H-1-Benzopyran-2-one,6-methoxy-;AKOS006346189;SY300566;TS-02433;CS-0324191;FT-0762252;AR-683/40724488

Chemical Property of 6-Methoxycoumarin

Chemical Property:

• Vapor Pressure: 5.12E-05mmHg at 25°C
• Melting Point: 189-191 °C
• Refractive Index: 1.572
• Boiling Point: 348.2 °C at 760 mmHg
• Flash Point: 144.7 °C
• PSA: 39.44000
• Density: 1.248 g/cm³
• LogP: 1.80160
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 176.047344113
• Heavy Atom Count: 13
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

6-Methoxycoumarin ^*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: COC1=CC2=C(C=C1)OC(=O)C=C2

Technology Process of 6-Methoxycoumarin

There total 31 articles about 6-Methoxycoumarin 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: 100.0%

4-methoxyphenyl propynoate (90920-97-1) → 6-methoxycoumarin (17372-53-1)

Guidance literature:

With Echavarren's catalyst; In dichloromethane; at 18 ℃; for 1h;

DOI:10.1021/acs.joc.0c02011

Reference yield: 98.0%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 6-methoxycoumarin (17372-53-1)

Guidance literature:

With N,N-diethylaniline; Reflux;

DOI:10.1016/j.bmcl.2008.08.102

Reference yield: 96.0%

3-(2-Hydroxy-5-methoxy-phenyl)-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester (114106-34-2) → 6-methoxycoumarin (17372-53-1)

Guidance literature:

With potassium carbonate; In acetone; for 1.5h; Heating;

upstream raw materials:

diazomethane

6-hydroxycoumarin

2-hydroxy-5-methoxybenzaldehyde

acetic anhydride

Downstream raw materials:

3,4-dihydro-6-methoxy-4-phenyl-2H-1-benzopyran-2-one

C₁₈H₁₃NO₅

C₁₈H₁₃NO₅

C₁₉H₁₆O₄

Refernces

• 1、 Wei, Jia,Wang, Pengcheng,Jia, Qianfa,Huang, Jiaoyao,Du, Zhiyun,Zhang, Kun,Wang, Jian. "Amine-catalyzed cascade synthesis of 3,4-diunsubstituted coumarins". . p. 4499 - 4502. Retrieved 2013.
• 2、 Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.. "Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes". . p. 178 - 198. Retrieved 2020/12/22.
• 3、 Jin, Can,Yan, Zhiyang,Sun, Bin,Yang, Jin. "Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters". supporting information. p. 2064 - 2068. Retrieved 2019/04/11.