Accetto Utilizziamo cookies per migliorare il nostro servizio e realizzare statistiche. Questa funzione puó essere disattivata cambiando la configurazione del browser. Continuando a navigare senza modificare questi parametri, consideriamo che l’uso di cookies sia accettato
Phenylacetylene is involved in the preparation of styrene by reduction using Lindlar catalyst. It is used to study the mechanism of the palladium-catalyzed phenyl acetylene oxidative carbonylation reaction. It is also used in the polymerization process to prepare polyphenylacetylene namely 1,2,4-triphenylbenzene and 1,3,5-triphenylbenzene.
Conversion to the 1-bromoalkyne has been described: Org. Synth. Coll., 5, 921 (1973). For an improved phase-transfer method, using NaBr/NaOCl, see: J. Org. Chem., 57, 4555 (1992).
For cyanation with CuCN in the presence of TMS chloride and NaI, see: Tetrahedron Lett., 34, 591 (1993).
Glaser oxidative coupling by Cu(OAc)2 in pyridine gives diphenylbuta-1,3-diyne: Org. Synth. Coll., 5, 499 (1973).
For conversion to the Grignard with ethylmagnesium bromide, and subsequent Cu-catalyzed coupling with allyl bromide, see: Org. Synth. Coll., 6, 925 (1988).
For preparation of the cuprate and references for coupling with aryl halides to give diarylacetylenes, see: Org. Synth. Coll., 6, 916 (1988).
Dimetallation can be accomplished with a 2:1 molar mixture of n-BuLi and KO-t-Bu in THF, the second metallation occurring specifically at the ortho-position. Thus, the bis(TMS)-derivative can be prepared in excellent yield: J. Org. Chem., 55, 1311 (1990).
Weerachawanasak, P.; Praserthdam, P.; Panpranot, J. Liquid-Phase Hydrogenation of Phenylacetylene Over the Nano-Sized Pd/TiO2 Catalysts. J. Nanosci. Nanotechnol. 2014, 14 (4), 3170-3175.
Yoshida, H.; Zama, T.; Fujita, S. I.; Panpranot, J.; Arai, M. Liquid phase hydrogenation of phenylacetylene over Pd and PdZn catalysts in toluene: effects of alloying and CO2 pressurization. RSC Adv. 2014, 4 (47), 24922-24928.
Dichiarazioni di rischio (UE): H226-H319-H335-H304
Flammable liquid and vapour. Causes serious eye irritation. May cause respiratory irritation. May be fatal if swallowed and enters airways.
Dichiarazioni precauzionali: P261-P280f-P305+P351+P338-P301+P330+P331-P315
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Get immediate medical advice/attention.