Misplaced Pages

Methyl propiolate

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Methyl propiolate
Names
Preferred IUPAC name Methyl prop-2-ynoate
Other names methyl propynoate
methyl acetylenecarboxylate
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 4-02-00-01688
ChemSpider
ECHA InfoCard 100.011.894 Edit this at Wikidata
EC Number
  • 213-083-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3Key: IMAKHNTVDGLIRY-UHFFFAOYSA-N
SMILES
  • COC(=O)C#C
Properties
Chemical formula C4H4O2
Molar mass 84.074 g·mol
Appearance colorless liquid
Density 0.945 g mL
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 , 100 kPa). Infobox references
Chemical compound

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. For example it is a potent dienophile. It has been widely evaluated as a precursor to heterocycles. including 1,3-dipolar cycloadditions.

References

  1. Hirst, Gavin C. (2001). "Methyl Propiolate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm237. ISBN 0471936235.
  2. 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.
  3. 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.
  4. 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.
Categories: