{{Chembox | ImageFile = MePropiolate.png | ImageSize = | ImageAlt = | PIN = Methyl prop-2-ynoate | OtherNames = methyl propynoate<br />methyl acetylenecarboxylate |Section1={{Chembox Identifiers | CASNo = 922-67-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = T88NXO102K | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 13536 | ChemSpiderID = 12948 | EINECS = 213-083-5 | Beilstein = 4-02-00-01688 | InChI=1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3 | InChIKey = IMAKHNTVDGLIRY-UHFFFAOYSA-N | SMILES = COC(=O)C#C }} |Section2={{Chembox Properties | C=4|H=4|O=2 | MolarMass = | Appearance = colorless liquid | Density = 0.945 g mL<sup>−1</sup> | MeltingPt = | BoilingPtC = 103-105 | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Methyl propiolate''' is an [[organic compound]] with the formula HC<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>. 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.<ref>{{cite encyclopedia|first=Gavin C.|last=Hirst|year=2001|doi=10.1002/047084289X.rm237|encyclopedia=[[Encyclopedia of Reagents for Organic Synthesis]]|chapter=Methyl Propiolate|isbn = 0471936235}}</ref> For example it is a potent [[dienophile]].<ref>{{cite journal |doi=10.1016/s0040-4020(02)00410-6 |title=Quantitative characterization of the global electrophilicity power of common diene/Dienophile pairs in Diels–Alder reactions |date=2002 |last1=Domingo |first1=Luis R. |last2=Aurell |first2=M.José |last3=Pérez |first3=Patricia |last4=Contreras |first4=Renato |journal=Tetrahedron |volume=58 |issue=22 |pages=4417–4423 |hdl=10533/173179 |hdl-access=free }}</ref> It has been widely evaluated as a precursor to [[heterocycle]]s.<ref>{{cite journal |doi=10.1021/ja201143v |title=Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies |date=2011 |last1=Guimond |first1=Nicolas |last2=Gorelsky |first2=Serge I. |last3=Fagnou |first3=Keith |journal=Journal of the American Chemical Society |volume=133 |issue=16 |pages=6449–6457 |pmid=21452842 }}</ref> including [[1,3-Dipolar cycloaddition|1,3-dipolar cycloadditions]].<ref>{{cite journal |doi=10.1021/ol060283l |title=Reusable Polymer-Supported Catalyst for the [3+2] Huisgen Cycloaddition in Automation Protocols |date=2006 |last1=Girard |first1=Christian |last2=Önen |first2=Esra |last3=Aufort |first3=Marie |last4=Beauvière |first4=Sophie |last5=Samson |first5=Edmond |last6=Herscovici |first6=Jean |journal=Organic Letters |volume=8 |issue=8 |pages=1689–1692 |pmid=16597142 }}</ref>
==References== <references />
[[Category:Alkyne derivatives]] [[Category:Methyl esters]] [[Category:Carboxylate esters]]