4-Ethoxycoumarin

Base Information

• Chemical Name: 4-Ethoxycoumarin
• CAS No.: 35817-27-7
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.199
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID50350961
• Nikkaji Number: J267.278B
• Wikidata: Q82127031
• Metabolomics Workbench ID: 74276
• Mol file: 35817-27-7.mol

Synonyms:4-Ethoxycoumarin;35817-27-7;4-ethoxy-2h-chromen-2-one;4-ethoxychromen-2-one;4-Ethoxy-chromen-2-one;Maybridge1_007528;4-Ethoxycoumarin, 97%;SCHEMBL15842782;HMS562O04;DTXSID50350961;FLZDKBHAUILYAZ-UHFFFAOYSA-N;CCG-34538;MFCD00052755;AKOS015838834;AS-56773;PD159113;E0545;FT-0618387;D90538;A822985;[(E)-(1-methyl-2-methylsulfinyl-propylidene)amino] N-methylcarbamate

Chemical Property of 4-Ethoxycoumarin

Chemical Property:

• Vapor Pressure: 2.97E-05mmHg at 25°C
• Melting Point: 134-138 °C(lit.)
• Refractive Index: 1.569
• Boiling Point: 356.2 °C at 760 mmHg
• Flash Point: 148.4 °C
• PSA: 39.44000
• Density: 1.21 g/cm³
• LogP: 2.19170
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 190.062994177
• Heavy Atom Count: 14
• Complexity: 257

Purity/Quality:

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

4-Ethoxycoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC(=O)OC2=CC=CC=C21
• Uses: 4-Ethoxycoumarin may be used in the preparation of 2-substituted-6-(2-hydroxyphenyl)-4(3H)-pyrimidones. It may also be used to synthesize 2,2-diphenyl-4-chromanone and 2,2-dimethyl-4-chromanone.

Technology Process of 4-Ethoxycoumarin

There total 10 articles about 4-Ethoxycoumarin 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: 90.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + acetylenedicarboxylic acid diethyl ester (762-21-0) → 4-ethoxy-2H-chromen-2-one (35817-27-7)

Guidance literature:

With 1-methyl-1H-imidazole; In neat (no solvent); at 100 ℃; for 0.116667h; Microwave irradiation; Green chemistry;

DOI:10.2298/JSC131223027D

Reference yield: 85.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → 4-ethoxy-2H-chromen-2-one (35817-27-7)

Guidance literature:

With indium; In N,N-dimethyl-formamide; at 60 ℃; for 12h; regioselective reaction;

DOI:10.1002/ejoc.201301788

Reference yield:

3H-chromene-2,4-dione (4438-85-1) + ethyl iodide (75-03-6) → 4-ethoxy-2H-chromen-2-one (35817-27-7)

Guidance literature:

With ethanol; sodium ethanolate;

DOI:10.1021/ja01569a056

upstream raw materials:

4-chloro-2H-1-benzopyran-2-one

sodium ethanolate

3H-chromene-2,4-dione

ethanol

Downstream raw materials:

1-(2-hydroxy-phenyl)-3-(2-oxo-cyclohexyl)-propane-1,3-dione

2,2-diphenylchroman-4-one

2-(2-oxo-cyclohexyl)-chromen-4-one

Refernces

• 1、 Chowdhury, Sushobhan,Chanda, Tanmoy,Gupta, Ashutosh,Koley, Suvajit,Ramulu, B. Janaki,Jones, Raymond C. F.,Singh, Maya Shankar. "Indium(0)-mediated Csp 3-S/O cross-coupling approach towards the regioselective alkylation of α-enolic esters/dithioesters: A mechanistic Insight". supporting information. p. 2964 - 2971. Retrieved 2014/05/20.