Methyl coumalate, 98%

Description

CAS: 6018-41-3 | C7H6O4 | 154.121 g/mol

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
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.

Solubility
Freely soluble in dichloromethane.

Notes
Stable under recommended storage conditions. Incompatible with oxidizing agents.

Specifications

Chemical Identifiers

• CAS: 6018-41-3
• Molecular Formula: C7H6O4
• Molecular Weight (g/mol): 154.121
• MDL Number: MFCD00010120
• InChI Key: HHWWWZQYHPFCBY-UHFFFAOYSA-N
• Synonym: methyl coumalate, methyl 2-oxo-2h-pyran-5-carboxylate, coumalic acid, methyl ester, 5-carbomethoxy-2-pyrone, 2h-pyran-5-carboxylic acid, 2-oxo-, methyl ester, coumalic acid methyl ester, unii-1s7tmf0r8t, methyl 2-pyrone-5-carboxylate, methyl 2-oxopyran-5-carboxylate, 1s7tmf0r8t
• PubChem CID: 80113
• IUPAC Name: methyl 6-oxopyran-3-carboxylate
• SMILES: COC(=O)C1=COC(=O)C=C1

• Melting Point: 68°C to 72°C
• Boiling Point: 178°C to 180°C (60 mmHg)
• Quantity: 10 g
• Merck Index: 14,2557
• Solubility Information: Freely soluble in dichloromethane.
• Formula Weight: 154.12
• Percent Purity: 98%
• Chemical Name or Material: Methyl coumalate

Safety and Handling

EINECSNumber	227-871-1
TSCA	No
Recommended Storage	Ambient temperatures

SDS

RUO – Research Use Only