Methyl propiolate

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]

Methyl propiolate

Names
Preferred IUPAC name Methyl prop-2-ynoate
Other names methyl propynoate methyl acetylenecarboxylate
Identifiers
CAS Number	922-67-8 Y
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 Y
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

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.