102487-14-9

Basic information

• Product Name: 5-phenylpenta-2,4-diyn-1-yl acetate
• Synonyms: 5-phenylpenta-2,4-diyn-1-yl acetate
• CAS NO: 102487-14-9
• Molecular Weight: 198.221
• Mol File: 102487-14-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5-phenylpenta-2,4-diyn-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenylpenta-2,4-diyn-1-yl acetate(102487-14-9)
• EPA Substance Registry System: 5-phenylpenta-2,4-diyn-1-yl acetate(102487-14-9)

Safety Data

• Hazardous Substances Data: 102487-14-9(Hazardous Substances Data)

Upstream product

• 627-09-8 Propargyl acetate 
• 536-74-3 phenylacetylene 
• 57272-05-6 prop-2-yn-1-yl hydrogen carbonate 
• 71022-74-7 (E)-1,2-diiodostyrene 
• 932-87-6 1-Bromo-2-phenylacetylene 

Relevant articles and documents

A General and Highly Selective Palladium-Catalyzed Hydroamidation of 1,3-Diynes

A chemo-, regio-, and stereoselective mono-hydroamidation of (un)symmetrical 1,3-diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α-alkynyl-α, β-unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density-functional theory (M06L-SMD) computations also suggest the crucial role of the substrate in controlling the regioselectivity of unsymmetrical 1,3-diynes.

Glaser-Hay hetero-coupling in a bimetallic regime: A Ni(II)/Ag(i) assisted base, ligand and additive free route to selective unsymmetrical 1,3-diynes

A Ni(OAc)2/Ag(OTf) catalysed coupling of aryl alkynes and propargylic alcohol/ether/ester gave the corresponding unsymmetrical 1,3-diynes in good to excellent yields. The reaction does not require bases, ligands or additives and shows excellent hetero-selectivity, thereby addressing the current challenges in the field of coupling of two different terminal alkynes.

Investigation of an efficient palladium-catalyzed C(sp)-C(sp) cross-coupling reaction using phosphine-olefin ligand: Application and mechanistic aspects

A π-acceptor phosphine-electron-deficient olefin ligand was found effective in promoting Pd-catalyzed C(sp)-C(sp) cross-coupling reactions. The new protocol realized the cross-coupling of a broad scope of terminal alkynes and haloalkynes in good to excellent yields with high selectivities. Electron-rich alkynes, which are normally difficult substrates in Glaser couplings, could be employed as either nucleophiles or electrophiles. Alkynes bearing similar substituents, such as n-C5H11CCBr and n-C4H9CCH, which usually suffer from homocoupling side reactions under Cadiot-Chodkiewicz conditions, were successfully cross-coupled in the system. Preliminary kinetic studies revealed that the reaction rate was zero-order in the concentrations of both haloalkynes and terminal alkynes and first order in the loading of Pd(dba)2 and exhibited no obvious dependence on the loading of the copper salt. Control experiments with other phosphines such as PPh3 and DPPF as the ligand were carried out. All the kinetic evidence indicated that the phosphine-olefin ligand facilitated the reductive elimination in the catalytic cycle.