Ethyl propiolate
Ethyl propiolate
  • CAS No.:623-47-2
Other grades of this product :
Ethyl propiolate Basic information
Product Name:Ethyl propiolate
Synonyms:ACETYLENECARBOXYLIC ACID ETHYL ESTER;ETHYL PROPIOLATE;ETHYL ACETYLENECARBOXYLATE;EPL;(Ethoxycarbonyl)acetylene;2-Propynoic acid, ethyl ester;Ethyl 2-propynoate;Ethyl propynoate
CAS:623-47-2
MF:C5H6O2
MW:98.1
EINECS:210-795-8
Product Categories:Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;Acids and Derivatives;Miscellaneous;Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;bc0001
Mol File:623-47-2.mol
Ethyl propiolate Chemical Properties
Melting point 9°C
Boiling point 120 °C (lit.)
density 0.968 g/mL at 25 °C (lit.)
refractive index n20/D 1.412(lit.)
Fp 74 °F
storage temp. 2-8°C
solubility Miscible with alcohol.
form Liquid
Specific Gravity0.968
color Clear colorless to pale yellow
Water Solubility miscible
Merck 14,3846
BRN 878250
CAS DataBase Reference623-47-2(CAS DataBase Reference)
NIST Chemistry ReferenceEthyl propiolate(623-47-2)
Safety Information
Hazard Codes Xi,F
Risk Statements 10-36/37/38-36-11
Safety Statements 26-36-37/39-16-33-29-24-23
RIDADR UN 3272 3/PG 3
WGK Germany 3
Hazard Note Irritant
HazardClass 3
PackingGroup II
HS Code 29161980
MSDS Information
ProviderLanguage
Ethyl propiolate English
SigmaAldrich English
ACROS English
ALFA English
Ethyl propiolate Usage And Synthesis
Chemical PropertiesEthyl propiolate is a clear colorless to pale yellow liquid that is soluble in ethanol, ether and chloroform. It an important organic chemical raw material and pharmaceutical intermediate. Ethyl propargylate is obtained by oxidation of propargyl alcohol to propargylic acid followed by esterification.
UsesHalogenated derivatives were used as substrates for direct, asymmetric alkynylation of cyclic ?-ketoesters using chiral phase-transfer catalysts. Also employed in a one-pot , four-component synthesis of benzene-1,2,3,5-tetracarboxylates promoted by Ph3P.
UsesIn organic synthesis; peptide coupling reagent.
UsesEthyl propiolate is used as a precursor in the preparation of substituted anthraquinones and pyrazolo[1,5-a]pyridine, which exhibits anti-inflammatory activity. Further, it is employed in the synthesis of benzene-1,2,3,5-tetracarboxylates promoted by triphenylphosphine. Its halogenated derivatives are used as a substrate for direct, asymmetric alkynylation of cyclic beta-ketoesters using chiral phase-transfer catalysts.
DefinitionChEBI: Ethyl propiolate is the ethyl ester of prop-2-ynoic acid. It is a ynoate ester, a terminal acetylenic compound and an ethyl ester.
HazardFlammable; lachrymator.

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