Methyl propiolate

Methyl propiolate
Names
	Preferred IUPAC name Methyl prop-2-ynoate
	Other names methyl propynoate; methyl acetylenecarboxylate
Identifiers
CAS Number	922-67-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	4-02-00-01688
ChemSpider	12948;
ECHA InfoCard	100.011.894
EC Number	213-083-5;
PubChem CID	13536;
UNII	T88NXO102K ;
CompTox Dashboard (EPA)	DTXSID60238923 ;
	InChI InChI=1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3 Key: IMAKHNTVDGLIRY-UHFFFAOYSA-N;
	SMILES COC(=O)C#C;
Properties
Chemical formula	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). Infobox references

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]

References

^ 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. hdl:10533/173179.
^ 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.

[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. hdl:10533/173179.

[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.

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