Methyl coumalate

Base Information

• Chemical Name: Methyl coumalate
• CAS No.: 6018-41-3
• Molecular Formula: C7H6 O4
• Molecular Weight: 154.122
• Hs Code.: 2932209090
• European Community (EC) Number: 227-871-1
• NSC Number: 137387,34627
• UNII: 1S7TMF0R8T
• DSSTox Substance ID: DTXSID00208923
• Nikkaji Number: J223.951E
• Wikidata: Q27252830
• Mol file: 6018-41-3.mol

Synonyms:Methyl coumalate;6018-41-3;Methyl 2-oxo-2H-pyran-5-carboxylate;5-(Carbomethoxy)-2-pyrone;2H-Pyran-5-carboxylic acid, 2-oxo-, methyl ester;methyl 6-oxopyran-3-carboxylate;Coumalic acid methyl ester;Coumalic acid, methyl ester;Methyl 2-pyrone-5-carboxylate;Methyl 2-Oxopyran-5-carboxylate;UNII-1S7TMF0R8T;1S7TMF0R8T;EINECS 227-871-1;MFCD00010120;NSC 34627;NSC-34627;NSC 137387;NSC-137387;Glutaconic acid, 4-(hydroxymethylene)-, .delta.-lactone, methyl ester;2H-Pyran-5-carboxylic acid, methyl ester;METHYL CUMALATE;Methyl coumalate, 98%;2-oxo-2H-pyran-5-carboxylic acid methyl ester;TimTec1_001696;SCHEMBL751528;CUMALIC ACID METHYL ESTER;DTXSID00208923;HMS1538N02;BCP27481;NSC34627;Methyl2-oxo-2H-pyran-5-carboxylate;NSC137387;methyl 6-oxo-6H-pyran-3-carboxylate;5-(METHOXYCARBONYL)-2-PYRONE;AKOS005068340;CS-W008753;PS-5739;COUMALIC ACID METHYL ESTER [MI];NCGC00174159-01;2-Pyrone-5-carboxylic Acid Methyl Ester;AC-27898;methyl 6-oxidanylidenepyran-3-carboxylate;SY018974;2-Oxopyran-5-carboxylic Acid Methyl Ester;6-oxo-3-pyrancarboxylic acid methyl ester;6-oxo-pyran-3-carboxylic acid methyl ester;C1734;FT-0628717;EN300-60829;6-Oxo-6H-pyran-3-carboxylic acid methyl ester;A15675;A833475;AE-508/40248460;Q27252830;Z955121426;Methyl 2-oxo-2H-pyran-5-carboxylate pound>>Coumalic acid methyl ester

Chemical Property of Methyl coumalate

Chemical Property:

• Appearance/Colour: WHITE TO TAN POWDER OR CRYSTALS
• Vapor Pressure: 0.00893mmHg at 25°C
• Melting Point: 65-67ºC
• Refractive Index: 1.4300 (estimate)
• Boiling Point: 265.9 °C at 760 mmHg
• Flash Point: 137 °C
• PSA: 56.51000
• Density: 1.326 g/cm₃
• LogP: 0.42640
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Freely soluble in dichloromethane.
• XLogP3: 0.4
• 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:

99% ^*data from raw suppliers

2-Oxo-2H-pyran-5-carboxylic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(=O)C=C1
• Uses: α, β-Unsaturated ketone Methyl Coumalate showed cytotoxicity against human normal gingival fibroblast cells and oral squamous cell carcinoma cell line-2. Methyl coumalate is a 2-pyrone and acts as dienophile in Diels-Alder reaction. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts. It has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives. Methyl coumalate has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives.

Technology Process of Methyl coumalate

There total 11 articles about Methyl coumalate 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: 100.0%

methanol (67-56-1) + 2-oxo-2H-pyran-5-carbonyl chloride (23090-18-8) → methyl coumalate (6018-41-3)

Guidance literature:

DOI:10.1016/S0040-4039(00)81766-9

Reference yield: 92.0%

2H-pyran-2-one-5-carboxylic acid (500-05-0) + S-(1-butyn-3-yl)-O-methyl xanthate → methyl coumalate (6018-41-3)

Guidance literature:

In toluene; Heating;

DOI:10.1021/ja00100a045

Reference yield: 81.8%

methanol (67-56-1) + 2H-pyran-2-one-5-carboxylic acid (500-05-0) → methyl coumalate (6018-41-3)

Guidance literature:

for 3h; Reflux;

upstream raw materials:

methanol

2-oxo-2H-pyran-5-carbonyl chloride

2H-pyran-2-one-5-carboxylic acid

methyl 8-methoxy-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate

Downstream raw materials:

methyl 4-methylcoumalate

1-(3,4-dimethoxy-phenethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

6-oxo-1-phenethyl-1,6-dihydro-pyridine-3-carboxylic acid

4-anilinomethylene-pentenedioic acid-5-methyl ester