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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-H311-H314
Flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P264b-P270-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant