Ethyl Propiolate

Title: Ethyl Propiolate
CAS Registry Number: 623-47-2
CAS Name: 2-Propynoic acid ethyl ester
Additional Names: ethyl acetylenecarboxylate
Molecular Formula: C5H6O2
Molecular Weight: 98.10
Percent Composition: C 61.22%, H 6.16%, O 32.62%
Literature References: Michael acceptor in organic synthesis. Prepn: W. H. Perkin, Jr., J. L. Simonsen, J. Chem. Soc. 1907, 816. IR spectrum and rotational isomerism study: S. W. Charles et al., J. Mol. Struct. 26, 249 (1975). Use in photochemical addition reactions: G. Büchi, S. H. Feairheller, J. Org. Chem. 34, 609 (1969); in Michael addition reactions: A. Hong, J. M. Friedman, Synth. Commun. 27, 2971 (1997); in halo aldol reactions with aldehydes: D. Chen et al., Eur. J. Org. Chem. 2004, 3330. Review of use as a peptide coupling reagent: B. Iorga, J.-M. Campagne, Synlett 2004, 1826-1828.
Properties: Distills at 119° (745 mm); also reported as bp 122° (Büchi, Feairheller). d44 0.9788. d1515 0.9676. d2525 0.9583.
Boiling point: 119°; bp 122° (Büchi, Feairheller)
Density: d44 0.9788; d1515 0.9676; d2525 0.9583
Use: In organic synthesis; peptide coupling reagent.
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