# Methyl propiolate

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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

Chemical compound

**Methyl propiolate** is an [organic compound](/source/Organic_compound) with the formula HC2CO2CH3. It is the [methyl](/source/Methyl) [ester](/source/Ester) of [propiolic acid](/source/Propiolic_acid), the simplest acetylenic [carboxylic acid](/source/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](/source/Dienophile).[2] It has been widely evaluated as a precursor to [heterocycles](/source/Heterocycle).[3] including [1,3-dipolar cycloadditions](/source/1%2C3-Dipolar_cycloaddition).[4]

## References

1. **[^](#cite_ref-1)** Hirst, Gavin C. (2001). "Methyl Propiolate". *[Encyclopedia of Reagents for Organic Synthesis](/source/Encyclopedia_of_Reagents_for_Organic_Synthesis)*. [doi](/source/Doi_(identifier)):[10.1002/047084289X.rm237](https://doi.org/10.1002%2F047084289X.rm237). [ISBN](/source/ISBN_(identifier)) [0471936235](https://en.wikipedia.org/wiki/Special:BookSources/0471936235).

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1016/s0040-4020(02)00410-6](https://doi.org/10.1016%2Fs0040-4020%2802%2900410-6). [hdl](/source/Hdl_(identifier)):[10533/173179](https://hdl.handle.net/10533%2F173179).

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1021/ja201143v](https://doi.org/10.1021%2Fja201143v). [PMID](/source/PMID_(identifier)) [21452842](https://pubmed.ncbi.nlm.nih.gov/21452842).

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1021/ol060283l](https://doi.org/10.1021%2Fol060283l). [PMID](/source/PMID_(identifier)) [16597142](https://pubmed.ncbi.nlm.nih.gov/16597142).

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Adapted from the Wikipedia article [Methyl propiolate](https://en.wikipedia.org/wiki/Methyl_propiolate) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Methyl_propiolate?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.