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)

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

• Language:English Provider:Ethyl propiolate
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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.

Synthesis

The general procedure for the synthesis of ethyl propargylate from ethanol and propargylate was as follows: propargylate (310 μL, 5 mmol; Alfa Aesar, Ward Hill, MA; Catalog No. A13245) was dissolved in 13 mL of ethanol to form a colorless solution, followed by the slow addition of concentrated sulfuric acid (139 μL, 2.5 mmol) to this solution. The reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the reaction was quenched with 13 mL of water followed by extraction with dichloromethane (10 mL; three times). The organic phases were combined, washed sequentially with water (10 mL; three times) and brine (10 mL), and then dried with anhydrous Na2SO4 (Thermo Fisher Scientific, Pittsburgh, PA; catalog number S421-3). The solvent was removed by distillation under reduced pressure to give the light yellow oily product ethyl propiolate (177 mg, 36% yield). The product was characterized by 1H NMR (400 MHz, CDCl3, δ): 4.26 (q, 3JH-H = 7.1 Hz, CH2, 2H), 2.92 (s, C≡CH, 1H), 1.33 (t, 3JH-H = 7.2 Hz, CH3, 3H).

References

[1] Journal of the American Chemical Society, 1988, vol. 110, p. 3965
[2] Patent: US2016/264506, 2016, A1. Location in patent: Paragraph 0035
[3] Chemische Berichte, 1926, vol. 59, p. 1689
[4] Nippon Kagaku Zasshi, 1956, vol. 77, p. 1689,1691
[5] Chem.Abstr., 1959, p. 5163

Ethyl propiolate(623-47-2)Related Product Information

• Propiolic Acid
• Ethyl acetate
• Ethyl phenylacetate
• Trinexapac-ethyl
• Ethyl formate
• Ethylparaben
• ISOXADIFEN-ETHYL
• Ethyl acetoacetate
• Ethyl acrylate
• Ethyl cyanoacetate
• Ethyl Hexanoate
• Ethanol
• Methyl propiolate
• PROPYNOIC ACID AMIDE
• Ethyl silicate
• ETHYL 2-HEXYNOATE
• ETHYL PHENYLPROPIOLATE
• TERT-BUTYL PROPIOLATE