Ethyl propiolate

• Catalog No.: A15068
• CAS Number: 623-47-2
• M. F.: C5H6O2
• M. W.: 98.09994
• Purity: 99%

SYNONYMS

• Title: 丙炔酸乙酯
• IUPAC name: ethyl prop-2-ynoate
• IUPAC Traditional name: ethyl propiolate
• Synonyms: Ethyl acetylenecarboxylate; Propiolic acid ethyl ester

DATABASE IDS

• EC Number: 210-795-8
• MDL Number: MFCD00009184
• CAS Number: 623-47-2
• Beilstein Number: 878250

PROPERTIES

• Purity: 99%
• Boiling Point: 118-120°C
• Density: 0.963
• Flash Point: 23°C(73°F)
• Melting Point: 9°C
• Refractive Index: 1.4120
• GHS Hazard statements: H226-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-36/37/38
• Safety Statements: 26-37-60
• TSCA Listed: 否
• Hazard Class: 3
• UN Number: UN3272
• Packing Group: III

REFERENCES

• Regio- and stereospecific hydrohalogenation of propiolic acid derivatives is illustrated by the conversion of ethyl propiolate to (Z)-3-bromo-2-propenoate in the presence of LiBr + acetic acid in acetonitrile: J. Org. Chem., 57, 709 (1992); Org. Synth. Coll., 9, 412 (1998).
• n-BuLi gives the alkynyllithium derivative, stable at low temperatures: J. Org. Chem., 45, 28 (1980). For use in a sequence for the synthesis of butenolides, see: J. Am. Chem. Soc., 101, 1544 (1979):
  
• Conjugate addition of allylic alcohols in the presence of trimethylamine proceeds via an intermediate betaine and leads to allyl vinyl ethers which undergo the Claisen rearrangement to give δ-unsaturated aldehydes: J. Org. Chem., 48, 5406 (1983); Org. Synth. Coll., 8, 536 (1993):