MilliporeSigma
All Photos(2)

261432

Sigma-Aldrich

Methyl coumalate

98%

Synonym(s):
Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate
Empirical Formula (Hill Notation):
C7H6O4
CAS Number:
Molecular Weight:
154.12
Beilstein:
126301
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.

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.

Packaging

1, 10 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service