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261432

Sigma-Aldrich

Methyl coumalate

98%

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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:
126301
EC Number:
227-871-1
MDL number:
MFCD00010120
PubChem Substance ID:
24855810
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

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This Item
C85409359475276030
Methyl coumalate 98%

Sigma-Aldrich

261432

Methyl coumalate

Coumalic acid 97%

Sigma-Aldrich

C85409

Coumalic acid

Methyl 2-oxo-2H-pyran-3-carboxylate 98%

Sigma-Aldrich

359475

Methyl 2-oxo-2H-pyran-3-carboxylate

2,3-Dimethoxy-1,3-butadiene 95%

Sigma-Aldrich

276030

2,3-Dimethoxy-1,3-butadiene

form

solid

form

powder

form

powder

form

liquid

bp

178-180 °C/60 mmHg (lit.)

bp

218 °C/120 mmHg (lit.)

bp

146-148 °C/0.75 mmHg (lit.)

bp

134-136 °C/745 mmHg (lit.)

mp

65-67 °C (lit.)

mp

203-205 °C (dec.) (lit.)

mp

75-77 °C (lit.)

mp

19 °C (lit.)

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 Code

11 - 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

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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)
Diels-Alder reaction of methyl coumalate with 1, 3-dienes.
Imagawa T, et al.
Tetrahedron, 30(14), 2227-2231 (1974)

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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