Methyl coumalate
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
Identifiers & Physical Properties
| CAS No. | 6018-41-3 |
|---|---|
| Molecular formula | C7H6O4 |
| Average molar mass | 154.12 g/mol |
| Monoisotopic mass | 154.02660867 g/mol |
| SMILES | COC(=O)c1ccc(=O)oc1 |
| InChIKey | HHWWWZQYHPFCBY-UHFFFAOYSA-N |
| PubChem CID | 80113 |
| EC No. | 227-871-1 |
| DTXSID | DTXSID00208923 |
Chemical & Physical Properties
| XLogP | 0.4 |
|---|---|
| Topological polar surface area | 52.6 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 2 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 249 |
| SpringerMaterials Properties | Chemical shift |
| 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 conditions | Inert atmosphere,Room Temperature |
| Solubility | Freely soluble in dichloromethane. |
| Physical state | 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 (partition coefficient) | -0.660 (est) |
| CAS DataBase Reference | 6018-41-3(CAS DataBase Reference) |
| FDA UNII | 1S7TMF0R8T |
| NIST Chemistry Reference | 2H-Pyran-5-carboxylic acid, 2-oxo-, methyl ester(6018-41-3) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS08 |
| Signal word | Warning |
| GHS hazard statements | H317-H334-H351b |
| GHS precautionary statements | P201-P202-P261-P272-P280g-P302+P352-P308+P313-P363-P403-P501c |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| Customs code | 2932209090 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
|---|---|
| Water hazard class (WGK) | 3 |
| Customs code | 2932209090 |
| Signal word | Warning |
| GHS pictogram | GHS08 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317-H334-H351b |
| GHS precautionary statements | P201-P202-P261-P272-P280g-P302+P352-P308+P313-P363-P403-P501c |
Applications & Uses
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.