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623-47-2 - Ethyl propiolate, 99% - Ethyl acetylenecarboxylate - Propiolic acid ethyl ester - A15068 - Alfa Aesar

A15068 Ethyl propiolate, 99%

CAS Number
623-47-2
Synonyms
Ethyl acetylenecarboxylate
Propiolic acid ethyl ester

Size Price ($) Quantity Availability
5g 36.33
25g 116.10
100g 289.35
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Ethyl propiolate, 99%

MDL
MFCD00009184
EINECS
210-795-8

Chemical Properties

Formula
C5H6O2
Formula Weight
98.10
Melting point
Boiling Point
118-120°
Flash Point
23°(73°F)
Density
0.963
Refractive Index
1.4120
Solubility
Miscible with alcohol.

Applications

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.

Notes

Incompatible with oxidizing agents, bases and acids.

Literature References

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):

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).

Al-Masum, M.; Shaban, W. Microwave irradiated Pd-catalyzed C(sp)-H activation and cross-coupling with styryltrifluoroborates. Tetrahedron Lett. 2015, 56 (11), 1437-1440.

Iwata, A.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. Tetrahedron 2015, 71 (37), 6580-6585.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
878250
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2916.19
TSCA
No

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