Methyl 2-oxo-2H-pyran-3-carboxylate

Base Information

• Chemical Name: Methyl 2-oxo-2H-pyran-3-carboxylate
• CAS No.: 25991-27-9
• Molecular Formula: C7H6O4
• Molecular Weight: 154.122
• Hs Code.: 2932209090
• European Community (EC) Number: 247-397-9
• DSSTox Substance ID: DTXSID40180653
• Nikkaji Number: J307.791H
• Mol file: 25991-27-9.mol

Synonyms:Methyl 2-oxo-2H-pyran-3-carboxylate;25991-27-9;3-Carbomethoxy-2-Pyrone;methyl 2-oxopyran-3-carboxylate;2H-pyran-3-carboxylic acid, 2-oxo-, methyl ester;EINECS 247-397-9;MFCD00075443;Methyl 2-pyrone-3-carboxylate;(methoxycarbonyl)pyranone;SCHEMBL1137507;DTXSID40180653;Methyl2-oxo-2H-pyran-3-carboxylate;AKOS015916479;AT11438;PS-9796;SY035712;CS-0091175;Methyl 2-oxo-2H-pyran-3-carboxylate, 98%;2-Oxo-2H-pyran-3-carboxylic acid methyl ester;J-016216

Chemical Property of Methyl 2-oxo-2H-pyran-3-carboxylate

Chemical Property:

• Appearance/Colour: Light yellow crystalline solid
• Vapor Pressure: 3.37E-05mmHg at 25°C
• Melting Point: 75-77 °C(lit.)
• Refractive Index: 1.513
• Boiling Point: 354.4 °C at 760 mmHg
• Flash Point: 158.7 °C
• PSA: 56.51000
• Density: 1.326 g/cm³
• LogP: 0.42640
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 154.02660867
• Heavy Atom Count: 11
• Complexity: 249

Purity/Quality:

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

Methyl 2-oxo-2H-pyran-3-carboxylate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=COC1=O
• Uses: Methyl 2-oxo-2H-pyran-3-carboxylate is used as a reagent to investigate alfa, beta-unsaturated carbonyl compounds for their cytotoxic profiles against oral human normal and tumor cells.

Technology Process of Methyl 2-oxo-2H-pyran-3-carboxylate

There total 3 articles about Methyl 2-oxo-2H-pyran-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: 41.0%

malonaldehydebis(dimethylacetal) (102-52-3) + malonic acid dimethyl ester (108-59-8) → methyl 2-oxo-2H-pyrane-3-carboxylate (25991-27-9)

Guidance literature:

malonaldehydebis(dimethylacetal); malonic acid dimethyl ester; With acetic anhydride; zinc(II) chloride; for 12.5h; Reflux; Inert atmosphere;

With formic acid; In water; for 1h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201908284

Reference yield:

C18H20N2O4 → methyl 2-oxo-2H-pyrane-3-carboxylate (25991-27-9) + cinnamaldehyde N,N-dimethylhydrazone (13466-39-2)

Guidance literature:

With tris{3-(heptafluoropropylhydroxymethylene)-camphorato}europium(III); In dichloromethane; at 80 ℃; for 4h;

DOI:10.1039/c8ob02132e

Reference yield:

→ methyl 2-oxo-2H-pyrane-3-carboxylate (25991-27-9)

Guidance literature:

DOI:10.1021/ja00788a034

upstream raw materials:

malonaldehydebis(dimethylacetal)

malonic acid dimethyl ester

Downstream raw materials:

(1R,4R,8R)-8-Cyclohexyloxy-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-4-carboxylic acid methyl ester

Refernces

• 1、 Hashimoto, Yoshimitsu,Abe, Ryo,Morita, Nobuyoshi,Tamura, Osamu. "Inverse-electron-demand Diels-Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones". . p. 8913 - 8916. Retrieved 2018/12/10.