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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.
Hazard Statements: H226-H319-H335-H304
Flammable liquid and vapour. Causes serious eye irritation. May cause respiratory irritation. May be fatal if swallowed and enters airways.
Precautionary Statements: 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.