Ethyl 4-oxo-4H-chromene-2-carboxylate

Base Information

• Chemical Name: Ethyl 4-oxo-4H-chromene-2-carboxylate
• CAS No.: 14736-31-3
• Molecular Formula: C12H10 O4
• Molecular Weight: 218.209
• Hs Code.: 2918300090
• European Community (EC) Number: 238-797-4
• DSSTox Substance ID: DTXSID80163687
• Nikkaji Number: J105.399J
• Wikidata: Q72476460
• ChEMBL ID: CHEMBL164781
• Mol file: 14736-31-3.mol

Synonyms:Ethyl 4-oxo-4H-chromene-2-carboxylate;14736-31-3;ethyl 4-oxochromene-2-carboxylate;Ethyl 4-oxo-4H-1-benzopyran-2-carboxylate;2-(Ethoxycarbonyl)chromone;4H-1-BENZOPYRAN-2-CARBOXYLIC ACID, 4-OXO-, ETHYL ESTER;Chromone-2-carboxylic acid ethyl ester;Ethylchromone-2-carboxylate;4-Oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester;Ethyl chromone-2-carboxylate;EINECS 238-797-4;BRN 0178173;CHEMBL164781;ethyl4-oxo-4H-chromene-2-carboxylate;Maybridge3_001728;SCHEMBL3359780;AMY6558;DTXSID80163687;Ethyl 4-oxochromen-2-carboxylate;HMS1435O12;BDBM50489181;MFCD00250077;AKOS016007296;CCG-242391;IDI1_013115;AS-40897;LS-39233;Ethyl 4-oxo-4H-chromene-2-carboxylate #;CS-0038062;FT-0708929;4-Oxo-4H-chromene-2-carboxylic acid ethyl ester;AQ-917/33531002;J-008349

Chemical Property of Ethyl 4-oxo-4H-chromene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.000237mmHg at 25°C
• Melting Point: 73-75℃
• Boiling Point: 325℃
• Flash Point: 143℃
• PSA: 56.51000
• Density: 1.289
• LogP: 1.96970
• Storage Temp.: 2-8°C
• 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%min ^*data from raw suppliers

Ethyl4-Oxo-4H-chromene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=O)C2=CC=CC=C2O1

Technology Process of Ethyl 4-oxo-4H-chromene-2-carboxylate

There total 16 articles about Ethyl 4-oxo-4H-chromene-2-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: 98.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) + oxalic acid diethyl ester (95-92-1) → ethyl 4-oxo-4H-1-benzopyran-2-carboxylate (14736-31-3)

Guidance literature:

With sodium ethanolate; In ethanol; for 1h; Heating;

DOI:10.1016/j.tet.2005.05.081

Reference yield: 95.0%

1-phenyl-2-hydroxyethanone (582-24-1) + oxalic acid diethyl ester (95-92-1) → 2-ethoxycarbonyl-4-oxo-4H-benzopyran (ethyl 4-oxochromene-2-carboxylate) + ethyl 4-oxo-4H-1-benzopyran-2-carboxylate (14736-31-3)

Guidance literature:

With sulfuric acid; sodium ethanolate; In ethanol; hexane; water; toluene;

Reference yield: 92.0%

acide chromone carboxylique-2 (4940-39-0) + ethanol (64-17-5) → ethyl 4-oxo-4H-1-benzopyran-2-carboxylate (14736-31-3)

Guidance literature:

With DPAT; In toluene; at 80 ℃; for 4h;

DOI:10.1021/ol101734k

upstream raw materials:

o-hydroxyacetophenone

oxalic acid diethyl ester

ethyl 2-hydroxy-4-oxochroman-2-carboxylate

ethanol

Downstream raw materials:

1-[4-(2-hydroxy-phenyl)-4-oxo-2-piperidino-crotonoyl]-piperidine

N-(pyridin-2-yl)-4-oxo-4H-chromene-2-carboxamide

Chromon-carbonsaeure-(2)-di-butylamid

4-(2-hydroxy-phenyl)-2-isopropylamino-4-oxo-crotonic acid isopropylamide

Refernces

• 1、 Sarkar, Debayan,Venkateswaran, Ramanathapuram V.. "Biomimetic type approach to the tricyclic core of xyloketals. Application to a short, stereocontrolled synthesis of alboatrin and first synthesis of xyloketal G". . p. 4559 - 4568. Retrieved 2011.
• 2、 Kandula, Venu,Gudipati, Ramakrishna,Chatterjee, Anindita,Kaliyaperumala, Muralidaran,Yennam, Satyanarayana,Behera, Manoranjan. "A novel synthesis of chromone based unnatural α -amino acid derivatives". . p. 1233 - 1245. Retrieved 2017.
• 3、 Helguera, Aliuska Morales,Perez-Garrido, Alfonso,Gaspar, Alexandra,Reis, Joana,Cagide, Fernando,Vina, Dolores,Cordeiro, M.Natalia D.S.,Borges, Fernanda. "Combining QSAR classification models for predictive modeling of human monoamine oxidase inhibitors". . p. 75 - 90. Retrieved 2013.
• 4、 Sakamoto, Masami,Yagishita, Fumitoshi,Kanehiro, Masayuki,Kasashima, Yoshio,Mino, Takashi,Fujita, Tsutomu. "Exclusive photodimerization reactions of chromone-2-carboxylic esters depending on reaction media". . p. 4435 - 4437. Retrieved 2010.
• 5、 Guan, Yong,Attard, Jonathan W.,Mattson, Anita E.. "Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions". . p. 1742 - 1747. Retrieved 2020/02/05.