3846. Ethyl Propiolate

Nomenclature

CAS number: 623-47-2
2-Propynoic acid ethyl ester; ethyl acetylenecarboxylate.
C5H6O2; mol wt 98.10.
C 61.22%, H 6.16%, O 32.62%.

Description and 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.

Chemical structure

Properties

Distills at 119° (745 mm); also reported as bp 122° (Büchi, Feairheller). d44 0.9788. d1515 0.9676. d2525 0.9583.

Use

In organic synthesis; peptide coupling reagent.