5,7-Dimethoxycoumarin

Base Information

• Chemical Name: 5,7-Dimethoxycoumarin
• CAS No.: 487-06-9
• Molecular Formula: C11H10O4
• Molecular Weight: 206.198
• Hs Code.: 2932209090
• European Community (EC) Number: 207-646-4
• NSC Number: 102793,217987
• UNII: JWE1QQ247N
• DSSTox Substance ID: DTXSID1041421
• Nikkaji Number: J6.016J
• Wikipedia: Citropten
• Wikidata: Q3599218
• Metabolomics Workbench ID: 45808
• ChEMBL ID: CHEMBL481049
• Mol file: 487-06-9.mol

Synonyms:5,7-dimethoxycoumarin;citropten;limettin;omphamurrayin

Chemical Property of 5,7-Dimethoxycoumarin

Chemical Property:

• Appearance/Colour: YELLOW TO TAN OR BROWN POWDER OR CRYSTALLINE POWDER
• Vapor Pressure: 3.13E-06mmHg at 25°C
• Melting Point: 146-149 °C(lit.)
• Refractive Index: 1.556
• Boiling Point: 388.1 °C at 760 mmHg
• Flash Point: 176.3 °C
• PSA: 48.67000
• Density: 1.248 g/cm³
• LogP: 1.81020
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 206.05790880
• Heavy Atom Count: 15
• Complexity: 274

Purity/Quality:

98% ^*data from raw suppliers

Citropten analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=CC(=O)O2)C(=C1)OC
• Uses: photosensitizing agent 5,7-Dimethoxycoumarin is a derivitized coumarin compound.

Technology Process of 5,7-Dimethoxycoumarin

There total 34 articles about 5,7-Dimethoxycoumarin 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: 95.0%

1-acetoxy-3,5-dimethoxy-benzene (23133-74-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → Limettin (487-06-9)

Guidance literature:

With formic acid; rhodium(II) acetate dimer; sodium acetate; In neat (no solvent); at 100 ℃; for 4h; regioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.joc.5b01713

Reference yield: 92.0%

2-hydroxy-4,6-dimethoxybenzaldehyde (708-76-9) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → Limettin (487-06-9)

Guidance literature:

In xylene; for 1h; Heating;

DOI:10.3987/COM-94-S(B)54

Reference yield: 90.0%

5,7-dihydroxy-2H-chromen-2-one (2732-18-5) + methyl iodide (74-88-4) → Limettin (487-06-9)

Guidance literature:

With potassium carbonate; In acetone; at 60 ℃; for 4h;

DOI:10.1021/np0497447

upstream raw materials:

diazomethane

5,7-dihydroxy-2H-chromen-2-one

5,7-dihydroxycoumarin 7-methyl ether

methanol

Downstream raw materials:

fraxinol

2-hydroxy-4,6-dimethoxy-trans-cinnamic acid

3-(2-hydroxy-4,6-dimethoxy-phenyl)-propionic acid

C₁₈H₁₆O₆

Refernces

• 1、 -. "Amido compounds as RORγt modulators and uses thereof". Page/Page column 72. . Retrieved 2017/09/30.
• 2、 Pasciak, Erick M.,Peters, Dennis G.. "Reduction of substituted phenyl 2-chloroacetates at silver cathodes: Electrosynthesis of coumarins". . p. G98 - G102. Retrieved 2015/04/14.