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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-H302-H312-H315-H319-H332-H335
Combustible liquid. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P235-P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing 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. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. 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. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant