16616-42-5

Basic information

• Product Name: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-phenyl-
• CAS NO: 16616-42-5
• Molecular Formula: C15H9ClO
• Molecular Weight: 240.689
• Mol File: 16616-42-5.mol
• Article Data: 148

Chemical Properties

• CAS DataBase Reference: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-phenyl-(16616-42-5)
• EPA Substance Registry System: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-phenyl-(16616-42-5)

Safety Data

• Hazardous Substances Data: 16616-42-5(Hazardous Substances Data)

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 144-62-7 oxalic acid 
• 536-74-3 phenylacetylene 
• 124-38-9 carbon dioxide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 201230-82-2 carbon monoxide 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 4998-15-6 4-chlorophenylglyoxal 
• 10557-21-8 1-(4-chlorophenyl)propane-1,2-dione 
• 89891-82-7 (4-chlorophenyl)ethynyl iodide 
• 611-73-4 Benzoylformic acid 
• 637-44-5 phenylpropyolic acid 
• 74-11-3 para-chlorobenzoic acid 
• 104-86-9 4-chlorobenzylamine 

Downstream Products

• 120422-20-0 1-(p-Chlorophenyl)-3-phenyl-3-(pyrid-2-ylamino)-2-propen-1-one 
• 120422-23-3 3-(5-Chloropyrid-2-ylamino)-1-(p-chlorophenyl)-3-phenyl-1-propen-1-one 
• 75371-70-9 (Z)-3-(p-chlorophenylamino)-1-(p-chlorophenyl)-3-phenyl-prop-2-en-1-one 
• 79202-87-2 6-(4-Chloro-phenyl)-2-oxo-4-phenyl-2H-pyran-3-carbonitrile 
• 71982-92-8 (Z)-1-(4-Chloro-phenyl)-3-phenyl-3-m-tolylamino-propenone 
• 69538-75-6 6-(4-chlorophenyl)-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile 
• 29784-26-7 (E)-1-(4-Chloro-phenyl)-3-phenyl-3-p-tolylamino-propenone 
• 1198463-86-3 (Z)-1-(4-chlorophenyl)-3-(2-methoxyphenylamino)-3-phenylprop-2-en-1-one 
• 1183859-91-7 dimethyl 5-chloro-1-oxo-3-phenyl-1H-inden-2-ylphosphonate 
• 1498-82-4 4-(4'-chlorophenyl)-2,6-diphenylpyridine 

Relevant articles and documents

Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6

A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.

Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia

(Matrix presented) Carbonylative coupling of phenylethyne with 4-methoxy-1-iodobenzene in the presence of 1 mol% PdCl2(PPh 3)2, 2 equiv of 0.5 M aqueous ammonia, and CO (1 atm) gives the corresponding α,β-alkynyl ketone in

Palladium nanoparticles supported on Smopex metal scavengers as catalyst for carbonylative Sonogashira reactions: Synthesis of α,β-alkynyl ketones

Palladium nanoparticles supported on two Smopex commercial metal scavengers (1% w/w) have been tested in the carbonylative Sonogashira reactions of aryl iodides with phenylacetylene. Their catalytic activity has been compared with those of more common catalysts (Pd/C, Pd/γ-Al 2O3). Pd/Smopex-234 resulted especially effective in the synthesis of alkynyl ketones even working with a low amount of palladium (0.2-0.5 mol%). Preliminary heterogeneity tests (i.e. hot filtration test, Pd leaching and recycle of the catalyst) have been performed in order to evaluate the catalytic behaviour of this system. The obtained results seem to indicate that Pd/Smopex-234 could act as a truly heterogeneous catalyst.

Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones

An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is

Synthesis of 2-isoxazolyl-2,3-dihydrobenzofuransviapalladium-catalyzed cascade cyclization of alkenyl ethers

A novel palladium-catalyzed cascade cyclization reaction of alkenyl ethers with alkynyl oxime ethers for the construction of poly-heterocyclic scaffolds has been developed, in which the electron-rich alkene moiety functions as a three-atom unit, simultaneously dealing well with the coordination and regioselectivity of electron-rich olefins under metal catalysis. The strategy features excellent regio- and chemoselectivities as well as good functional group tolerance. Moreover, the newly formed 2-isoxazolyl-2,3-dihydrobenzofuran products can be further transformed to diverse complex heterocycles, demonstrating their potential applications in organic synthesis and medicinal chemistry.