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Propiolic acid is a reagent used in the preparation of transition metal complexes, haloalkyl propiolates and halopropenoates.
Alkylation of the dilithio-derivative leads to higher 2-alkynoic acids. Reaction with epoxides, partial reduction (Lindlar) of the triple bond and cyclization has been used in the synthesis of unsaturated lactones: Tetrahedron Lett., 2615 (1974); J. Org. Chem., 40, 1610 (1975).
Sun, M.; Sargus, B. A.; Carey, S. J.; Kukolich, S. G. Measurements of deuterium quadrupole coupling in propiolic acid and fluorobenzenes using pulsed-beam Fourier transform microwave spectrometers. J. Chem. Phys 2015, 142 (15), 154306.
Jia, H.; Feng, H.; Sun, Z. Decarboxylative dipropargylation of primary amines with propiolic acids and formaldehyde via metal-free coupling. Tetrahedron 2015, 71 (18), 2724-2728.
Hazard Statements: H226-H301-H310-H314-H318
Flammable liquid and vapour. Toxic if swallowed. Fatal in contact with skin. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER/doctor 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.