261432

Methyl coumalate

98%

• Synonym(s): Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate
• Empirical Formula (Hill Notation): C₇H₆O₄
• CAS Number: 6018-41-3
• Molecular Weight: 154.12
• Beilstein/REAXYS Number: 126301
• EC Number: 227-871-1
• MDL number: MFCD00010120
• UNSPSC Code: 12352100
• PubChem Substance ID: 24855810
• NACRES: NA.22

Properties

• assay: 98%
• form: solid
• bp: 178-180 °C/60 mmHg (lit.)
• mp: 65-67 °C (lit.)
• SMILES string: COC(=O)C1=COC(=O)C=C1
• InChI: 1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3
• InChI key: HHWWWZQYHPFCBY-UHFFFAOYSA-N

Description

General description

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[3.2.1.0^2,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.

Application

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)