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Merck
CN

261432

Methyl coumalate

98%

Synonym(s):

Methyl 2-oxo-2H-pyran-5-carboxylate, Methyl 2-pyrone-5-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C7H6O4
CAS Number:
6018-41-3
Molecular Weight:
154.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24855810
EC Number:
227-871-1
Beilstein/REAXYS Number:
126301
MDL number:
MFCD00010120
Assay:
98%
Form:
solid

Key Documents

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InChI key

HHWWWZQYHPFCBY-UHFFFAOYSA-N

InChI

1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3

SMILES string

COC(=O)C1=COC(=O)C=C1

assay

98%

form

solid

bp

178-180 °C/60 mmHg (lit.)

mp

65-67 °C (lit.)

functional group

ester

Quality Level

200

Related Categories

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000516446
0000516446
0000242937
0000091366
0000242937

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Diels-Alder reaction of methyl coumalate with 1, 3-dienes.
Imagawa T, et al.
Tetrahedron, 30(14), 2227-2231 (1974)
Aromatics from pyrones: para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate.
Kraus GA, et al.
Green Chemistry, 13(10), 2734-2736 (2011)
Suqing Zheng et al.
Organic letters, 11(17), 3978-3981 (2009-08-13)
A phosphine-catalyzed [4 + 3] annulation of modified allylic carbonates with methyl coumalate was developed. This strategy offered a powerful method for the construction of bicyclo[3.2.2]nonadiene skeleton with high stereoselectivity.
Quinolizinium Compounds by Cyclization of Pyridones from Methyl Coumalate and ?-Phenylethylamines.
Wiley RH, et al.
Journal of the American Chemical Society, 75(18), 4482-4484 (1953)

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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