Ethyl coumarin-3-carboxylate

Base Information

• Chemical Name: Ethyl coumarin-3-carboxylate
• CAS No.: 1846-76-0
• Molecular Formula: C12H10O4
• Molecular Weight: 218.209
• Hs Code.: 29322090
• European Community (EC) Number: 811-043-7
• NSC Number: 620
• UNII: 27EAZ97E5V
• DSSTox Substance ID: DTXSID70171594
• Nikkaji Number: J24.843F
• Wikidata: Q83041675
• Metabolomics Workbench ID: 74293
• ChEMBL ID: CHEMBL591436
• Mol file: 1846-76-0.mol

Synonyms:ethyl 2-oxo-2H-chromene-3-carboxylate

Chemical Property of Ethyl coumarin-3-carboxylate

Chemical Property:

• Appearance/Colour: slightly yellow crystalline powder
• Vapor Pressure: 6.48E-06mmHg at 25°C
• Melting Point: 92-94 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 378 °C at 760 mmHg
• Flash Point: 195.6 °C
• PSA: 56.51000
• Density: 1.289 g/cm³
• LogP: 1.96970
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 218.05790880
• Heavy Atom Count: 16
• Complexity: 332

Purity/Quality:

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

ethyl2-oxo-2H-chromene-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=CC=CC=C2OC1=O

Technology Process of Ethyl coumarin-3-carboxylate

There total 49 articles about Ethyl coumarin-3-carboxylate 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: 99.0%

nitromethane (75-52-5) + ethanol (64-17-5) → ethyl coumarin-3-carboxylate (1846-76-0) + ethyl 2-ethoxycarbonyl-3-(2-hydroxyphenyl)-4-nitrobutyrate (126814-18-4)

Guidance literature:

With cesium fluoride; Title compound not separated from byproducts; Ambient temperature;

Reference yield: 98.0%

salicylaldehyde (90-02-8) + diethyl malonate (105-53-3) → ethyl coumarin-3-carboxylate (1846-76-0)

Guidance literature:

With 1,3-dimethylimidazolium sulfate monomethyl ester; L-proline; In water; at 90 ℃; for 1.33333h;

DOI:10.3390/molecules16064379

Reference yield: 95.0%

salicylaldehyde (90-02-8) + ethyl 2-cyanoacetate (105-56-6) → ethyl coumarin-3-carboxylate (1846-76-0)

Guidance literature:

With iron(III) chloride; In ethanol; at 80 ℃; for 24h; Mechanism;

DOI:10.1080/00397911.2013.862833

upstream raw materials:

piperidine

salicylaldehyde

diethyl malonate

2-acetoxybenzaldehyde

Downstream raw materials:

ethyl 3-(2-hydroxyphenyl)-2-methoxycarbonyl-4-nitrobutyrate

coumarin-3N-(4'-(N'-4,6-dimethyl-pyrimidinyl-2)sulphonamidophenyl)carboxamide

coumarin-3N-(4'-(N'-m-methylphenyl)sulphonamidophenyl)carboxamide

coumarin-3N-(4'-(N'-p-methylphenyl)sulphonamidophenyl)carboxamide

Refernces

• 1、 Tozzi, Silvia,Zanna, Nicola,Taddei, Paola. "Study on the interaction between gliadins and a coumarin as molecular model system of the gliadins-anthocyanidins complexes". . p. 3586 - 3597. Retrieved 2013.
• 2、 Fan, Li-Ping,Yang, Wei-Jun,Xu, Dong-Cheng,Li, Xin-Sheng,Xie, Jian-Wu. "Efficient methods for the synthesis of benzopyrano[3,4-c]pyrrolidines by catalyzed 1,3-dipolar cycloaddition of azomethine ylides with 3-substituted coumarins". . p. 3376 - 3384. Retrieved 2011.
• 3、 Valizadeh,Azimi. "ZnO/MgO Containing ZnO Nanoparticles as a Highly Effective Heterogeneous Base Catalyst for the Synthesis of 4H-Pyrans and Coumarins in [bmim]BF 4". . p. 123 - 130. Retrieved 2011.
• 4、 Shakil, Md. R.,Meguerdichian, Andrew G.,Tasnim, Habiba,Shirazi-Amin, Alireza,Seraji, Mohammad S.,Suib, Steven L.. "Syntheses of ZnO with Different Morphologies: Catalytic Activity toward Coumarin Synthesis via the Knoevenagel Condensation Reaction". . p. 5703 - 5714. Retrieved 2019.
• 5、 Jiang, Youhong,Li, Huiwen,Chen, Ruofei,Liu, Wei,Chen, Chunyang,Li, Zhongguo,Liu, Weisheng. "Novel fluorescent probe based on dicoumarin for rapid on-site detection of Hg2+ in loess". . . Retrieved 2021.
• 6、 Jin, Hui,Cho, Soo Min,Hwang, Geum-Sook,Ryu, Do Hyun. "Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins". . p. 163 - 167. Retrieved 2017.
• 7、 Shockravi, Abbas,Shargi, Hashem,Valizadeh, Hassan,Heravi, Majid M.. "Solvent free synthesis of coumarins". . p. 2555 - 2559. Retrieved 2002.
• 8、 Vashishtha, Manu,Mishra, Manish,Shah, Dinesh O.. "Organobase catalysis using 1-(2-pyrimidyl)piperazine in micellar medium: An approach for better performance and reusability of organobase". . p. 1339 - 1354. Retrieved 2016.
• 9、 Matsumura. "-". . p. 995,998. Retrieved 1961.
• 10、 Chen, Guo Feng,Zhang, Li Yan,Li, Hong Yang,Chen, Bao Hua. "Synthesis of coumarin derivatives containing 2-aminothiazole moiety and their recognition of metal ions". . p. 4273 - 4281. Retrieved 2015.