Methyl propiolate is an organic compound with the formula HC2CO2CH3. It is the methyl ester of propiolic acid, the simplest acetylenic carboxylic acid. It is a colorless liquid that is miscible with organic solvents. The compound is a reagent and building block for the synthesis of other organic compounds, reactions that exploit the electrophilicity of the alkyne group.[1] For example it is a potent dienophile.[2] It has been widely evaluated as a precursor to heterocycles.[3] including 1,3-dipolar cycloadditions.[4]
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| Names | |
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| Preferred IUPAC name
Methyl prop-2-ynoate | |
| Other names
methyl propynoate
methyl acetylenecarboxylate | |
| Identifiers | |
3D model (JSmol)
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| 4-02-00-01688 | |
| ChemSpider | |
| ECHA InfoCard | 100.011.894 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C4H4O2 | |
| Molar mass | 84.074 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.945 g mL−1 |
| Boiling point | 103–105 °C (217–221 °F; 376–378 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References
edit- ^ Hirst, Gavin C. (2001). "Methyl Propiolate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm237. ISBN 0471936235.
- ^ Domingo, Luis R.; Aurell, M.José; Pérez, Patricia; Contreras, Renato (2002). "Quantitative characterization of the global electrophilicity power of common diene/Dienophile pairs in Diels–Alder reactions". Tetrahedron. 58 (22): 4417–4423. doi:10.1016/s0040-4020(02)00410-6.
- ^ Guimond, Nicolas; Gorelsky, Serge I.; Fagnou, Keith (2011). "Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies". Journal of the American Chemical Society. 133 (16): 6449–6457. doi:10.1021/ja201143v. PMID 21452842.
- ^ Girard, Christian; Önen, Esra; Aufort, Marie; Beauvière, Sophie; Samson, Edmond; Herscovici, Jean (2006). "Reusable Polymer-Supported Catalyst for the [3+2] Huisgen Cycloaddition in Automation Protocols". Organic Letters. 8 (8): 1689–1692. doi:10.1021/ol060283l. PMID 16597142.