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4-Pentyn-1-ol is widely utilized in ring-opening polymerization reactions. It plays an important role as a starting reagent in stereo selective total synthesis of antimicrobial marine metabolites, ieodomycin A and B. It is also used in the preparation of 3-pent-4-ynyloxy phthalonitrile.
Readily forms a dilithio-derivative, allowing regioselective C-alkylation in the 5-position without the need for protection of the alcohol function. Thus, alkylation with the THP ether of 5-bromopentanol gives a 10-carbon chain as part of the synthesis of a macrolide pheromone, and in other natural product syntheses: J. Org. Chem., 58, 7535 (1993), and references therein./n
Fjermestad, T.; Ho, J. H. H.; Macgregor, S. A.; Messerle, B. A.; Tuna, D. Computational Study of the Mechanism of Cyclic Acetal Formation via the Iridium(I)-Catalyzed Double Hydroalkoxylation of 4-Pentyn-1-ol with Methanol. Organometallics 2011, 30 (3), 618-626.
Møllendal, H.; Dreizler, H.; Sutter, D. H. Structural and Conformational Properties of 4-Pentyn-1-ol As Studied by Microwave Spectroscopy and Quantum Chemical Calculations. J. Phys. Chem. A 2007, 111 (46), 11801-11808.
Hazard Statements: H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P260-P280g-P305+P351+P338
Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.