Coumestan

Base Information

• Chemical Name: Coumestan
• CAS No.: 479-12-9
• Molecular Formula: C15H8O3
• Molecular Weight: 236.227
• UNII: MT103Z562V
• DSSTox Substance ID: DTXSID30197316
• Nikkaji Number: J2.266.691F,J304.376B
• Wikipedia: Coumestan
• Wikidata: Q2608767
• NCI Thesaurus Code: C68532
• Metabolomics Workbench ID: 66007
• Mol file: 479-12-9.mol

Synonyms:(1)benzoxolo(3,2-c)chromen-6-one;coumestan

Chemical Property of Coumestan

Chemical Property:

• Vapor Pressure: 3.62E-07mmHg at 25°C
• Boiling Point: 417.2°C at 760 mmHg
• Flash Point: 206.1°C
• PSA: 43.35000
• Density: 1.385g/cm³
• LogP: 3.69240
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 236.047344113
• Heavy Atom Count: 18
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C(O2)C4=CC=CC=C4OC3=O

Technology Process of Coumestan

There total 12 articles about Coumestan 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: 60.0%

3-iodo-4-phenoxy-2H-chromen-2-one (68903-74-2) → 4-phenoxy-2H-1-benzopyran-2-one (35817-28-8) + coumestan (479-12-9)

Guidance literature:

With palladium on activated carbon; sodium acetate; In N,N-dimethyl acetamide; at 130 - 140 ℃; for 16h; Solvent; Catalytic behavior;

DOI:10.1039/c7ra12419h

Reference yield:

1-ethynyl-2-methoxybenzene (767-91-9) → coumestan (479-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / CuI; PdCl₂(PPh₃)2; Et₃N / dimethylformamide / 2 h / 60 °C

2: 95 percent / I₂ / CH₂Cl₂ / 12 h / 25 °C

3: 99 percent / PdCl₂(PPh₃)2; K₂CO₃ / dimethylformamide / 6 h / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; potassium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Sonogashira cross-coupling reaction;

DOI:10.1021/jo0517038

Reference yield:

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + 2-iodochlorobenzene (615-41-8) → 4-hydroxy-3-(2-chlorophenyl)coumarin (30014-86-9) + 4-hydroxy-3-phenylcoumarin (1786-05-6) + coumestan (479-12-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; for 3h; Inert atmosphere; Irradiation;

DOI:10.1016/j.tetlet.2010.08.013

upstream raw materials:

2,3-bis-(2-methoxy-phenyl)-3-oxo-propionitrile

3-diazo-2,3-dihydro-2-benzofuranone

1-ethynyl-2-methoxybenzene

4-hydroxy[1]benzopyran-2-one