Methyl coumalate Chemical Properties

Melting point:

65-67 °C (lit.)

Boiling point:

178-180 °C/60 mmHg (lit.)

Density 

1.1993 (rough estimate)

refractive index 

1.4300 (estimate)

Flash point:

178-180°C/60mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Freely soluble in dichloromethane.

form 

powder to crystal

color 

White to Orange to Green

Merck 

14,2557

BRN 

126301

InChI

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

InChIKey

HHWWWZQYHPFCBY-UHFFFAOYSA-N

SMILES

C1(=O)OC=C(C(OC)=O)C=C1

LogP

-0.660 (est)

CAS DataBase Reference

6018-41-3(CAS DataBase Reference)

NIST Chemistry Reference

2H-Pyran-5-carboxylic acid, 2-oxo-, methyl ester(6018-41-3)

Safety Information

WGK Germany 

3

HS Code 

2932209090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl coumalate Usage And Synthesis

Uses

α, β-Unsaturated ketone Methyl Coumalate showed cytotoxicity against human normal gingival fibroblast cells and oral squamous cell carcinoma cell line-2.

Uses

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.

Uses

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.

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.

Synthesis

General procedure for the synthesis of methyl coumalate from coumaric acid: diisopropylethylamine was added to a suspension of coumaric acid (115.5 g) in N-methylpyrrolidone (600 mL) at 25 °C. Subsequently, dimethyl sulfate (100.9 g) was slowly added over a period of 1 hour and the reaction mixture was stirred continuously for 2 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with toluene and extracted sequentially with water, sodium bicarbonate solution and water. Afterwards, toluene was removed under vacuum. The crude product, methyl coumalate, was purified by short distillation or crystallization combined with grinding. Finally, after removal of residual solvent by vacuum evaporation, methyl coumalate (78.8 g, 99% purity, 64% yield) was obtained.

References

[1] Patent: WO2004/792, 2003, A1. Location in patent: Page 15
[2] Tetrahedron Letters, 1983, vol. 24, # 17, p. 1771 - 1774
[3] Liebigs Annalen der Chemie, 1990, p. 233 - 238

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