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Ethyl propiolate

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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
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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.)
Flash point:
74 °F
storage temp. 
2-8°C
solubility 
Miscible with alcohol.
form 
Liquid
Specific Gravity
0.968
color 
Clear colorless to pale yellow
Water Solubility 
miscible
Merck 
14,3846
BRN 
878250
Dielectric constant
7.0
CAS DataBase Reference
623-47-2(CAS DataBase Reference)
NIST Chemistry Reference
Ethyl propiolate(623-47-2)
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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

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Ethyl propiolate Usage And Synthesis

Chemical Properties

Ethyl 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.

Uses

Halogenated 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.

Uses

Ethyl 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.

Uses

In organic synthesis; peptide coupling reagent.

Definition

ChEBI: Ethyl propiolate is the ethyl ester of prop-2-ynoic acid. It is a ynoate ester, a terminal acetylenic compound and an ethyl ester.

Hazard

Flammable; lachrymator.

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