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4,4-Dimethyl-2-pentyne is used in organometallic reactions for regioselectivity of its insertion into the Pd-C bond of cyclopalladated complexes. It is also used to prepare pyrimidine-dione by reacting with isocyanate in the presence of nickel/ N-heterocyclic carbene.
Pd-catalyzed coupling of acetylenes with iodoaromatic compounds with in situ cyclization has been employed as a route to various heterocycles. Several examples were reported with this alkyne in which a substituted oxygen heterocycle was obtained with good regioselectivity from o-iodo phenols, o-iodo benzyl alcohols or o-iodobenzoic acid derivatives: J. Org. Chem., 60, 3270 (1995):
Zhao, D.; Zhang, J.; Xie, Z. Facial Synthesis of o-Carborane-Substituted Alkenes and Allenes by a Regioselective Ene Reaction of 1,3-Dehydro-o-carborane. Chem. Eur. J. 2015, 21 (29), 10334-10337.
Villuendas, P.; Urriolabeitia, E. P. Ru-Catalyzed Regioselective CH-Hydroarylation of Alkynes with Benzylthioethers Using Sulfur as Directing Group. Org. Lett. 2015, 17 (12), 3178-3181.
Hazard Statements: H225-H304
Highly flammable liquid and vapour. May be fatal if swallowed and enters airways.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P280-P301+P310-P303+P361+P353-P331-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. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Do NOT induce vomiting. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant