methyl coumalate
2H-pyran-5-carboxylic acid, 2-oxo-, methyl ester (8CI)(9CI)
Identification
| Name | methyl coumalate |
| IUPAC | methyl 6-oxopyran-3-carboxylate |
| CAS Number | 6018-41-3 |
| EINECS | 227-871-1 |
| FDA UNII | 1S7TMF0R8T |
| Molecular Formula | C7 H6 O4 |
| Molecular Weight | 154.12162000 |
| MDL Number | MFCD00010120 |
| Nikkaji Number | J223.951E |
| Beilstein | 0126301 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 265.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 279.00 °F. TCC ( 137.00 °C. ) (est) |
| logP (o/w) | -0.660 (est) |
| Soluble in | water, 120 mg/L @ 37 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for methyl coumalate usage levels up to | not for fragrance use. |
| Recommendation for methyl coumalate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
coumalic acid, methyl ester
methyl 2-oxo-2H-pyran-5-carboxylate
methyl 6-oxopyran-3-carboxylate
2H-
pyran-5-carboxylic acid, 2-oxo-, methyl ester
2H-
pyran-5-carboxylic acid, 2-oxo-, methyl ester (8CI)(9CI)
PubMed:
Understanding the domino reaction between 3-chloroindoles and methyl coumalate yielding carbazoles. A DFT study.
PubMed:
Et3N-catalyzed tandem formal [4 + 3] annulation/decarboxylation/isomerization of methyl coumalate with imine esters: access to functionalized azepine derivatives.
PubMed:
First inverse electron-demand Diels-Alder methodology of 3-chloroindoles and methyl coumalate to carbazoles.
PubMed:
Phosphine-catalyzed [4 + 3] annulation for the synthesis of highly functionalized bicyclo[3.2.2]nonadienes.