Methyl coumalate
- Product Name
- Methyl coumalate
- CAS No.
- 6018-41-3
- Chemical Name
- Methyl coumalate
- Synonyms
- METHYL 2-OXO-2H-PYRAN-5-CARBOXYLATE;Coumalic acid methyl ester;Methyl coumaric acid;METHYL COUMALATE;TIMTEC-BB SBB000117;Methyl coumalate 98%;Methyl Coumalate >5-(Carbomethoxy)-2-pyrone;Methyl 2-pyrone-5-carboxylate;METHYL PYR-2-ONE-5-CARBOXYLATE
- CBNumber
- CB8755382
- Molecular Formula
- C7H6O4
- Formula Weight
- 154.12
- MOL File
- 6018-41-3.mol
Methyl coumalate Property
- 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
- WGK Germany
- 3
- HS Code
- 2932209090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H317May cause an allergic skin reaction
H334May cause allergy or asthma symptoms or breathing difficulties if inhaled
- Precautionary statements
-
P201Obtain special instructions before use.
P202Do not handle until all safety precautions have been read and understood.
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P272Contaminated work clothing should not be allowed out of the workplace.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P308+P313IF exposed or concerned: Get medical advice/attention.
P363Wash contaminated clothing before reuse.
P403Store in a well-ventilated place.
N-Bromosuccinimide Price
- Product number
- 261432
- Product name
- Methyl coumalate
- Purity
- 98%
- Packaging
- 10g
- Price
- $379
- Updated
- 2025/07/31
- Product number
- C1734
- Product name
- Methyl Coumalate
- Purity
- >96.0%(GC)
- Packaging
- 5g
- Price
- $76
- Updated
- 2025/07/31
- Product number
- C1734
- Product name
- Methyl Coumalate
- Purity
- >96.0%(GC)
- Packaging
- 25g
- Price
- $250
- Updated
- 2025/07/31
- Product number
- M294530
- Product name
- Methyl Coumalate
- Packaging
- 1g
- Price
- $50
- Updated
- 2021/12/16
- Product number
- 286342
- Product name
- 2-Oxo-2H-pyran-5-carboxylic acid methyl ester
- Packaging
- 2g
- Price
- $333
- Updated
- 2021/12/16
Methyl coumalate Chemical Properties,Usage,Production
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[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.
Synthesis
500-05-0
6018-41-3
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
Methyl coumalate Preparation Products And Raw materials
Raw materials
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View Lastest Price from Methyl coumalate manufacturers
- Product
- Methyl coumalate 6018-41-3
- Price
- US $50.00/kg
- Min. Order
- 1kg
- Purity
- 99
- Supply Ability
- 5000
- Release date
- 2024-11-21
- Product
- Methyl Coumalate 6018-41-3
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-02-12
- Product
- Methyl coumaric acid 6018-41-3
- Price
- US $48.00-40.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200tons
- Release date
- 2021-06-09