37166-46-4

Basic information

• Product Name: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-(trimethylsilyl)-
• CAS NO: 37166-46-4
• Molecular Formula: C12H13ClOSi
• Molecular Weight: 236.773
• Mol File: 37166-46-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-(trimethylsilyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-(trimethylsilyl)-(37166-46-4)
• EPA Substance Registry System: 2-Propyn-1-one, 1-(4-chlorophenyl)-3-(trimethylsilyl)-(37166-46-4)

Safety Data

• Hazardous Substances Data: 37166-46-4(Hazardous Substances Data)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 104-88-1 4-chlorobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 

Downstream Products

• 108715-11-3 ethyl 2-methyl-6-(4-chlorophenyl)pyridine-3-carboxylate 
• 1028866-37-6 rac-2-(4-chlorophenyl)-1-pyridin-2-yl-4-(trimethylsilanyl)but-3-yn-2-ol 
• 93523-45-6 3-(4-Chloro-phenyl)-1-trimethylsilanyl-pent-1-yn-3-ol 
• 22959-34-8 1-(4-chlorophenyl)-2-propyn-1-one 

Relevant articles and documents

Elemental iodine-catalyzed coupling of alkynylsilanes with acid chlorides: A facile synthesis of α,β-acetylenic ketones

Alkynylsilanes undergo coupling smoothly with acid chlorides in the presence of molecular iodine under mild reaction conditions to afford the corresponding α, β-acetylenic ketones in excellent yields in a short reaction time with high selectivity.

A phosphine-free, atom-efficient cross-coupling reaction of triorganoindiums with acyl chlorides catalyzed by immobilization of palladium(0) in MCM-41

The first phosphine-free heterogeneous palladium(0)-catalyzed cross-coupling of triorganoindiums with acyl chlorides has been developed that proceeds smoothly in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable aryl ketones and α,β-acetylenic ketones with high atom-economy and high yield. This phosphine-free heterogeneous palladium(0) catalyst can be easily prepared from commercially available reagents and recovered by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.

Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones

Bis(trimethylsilyl)acetylenes, Me3Si(CC)nSiMe3, react with acyl chloride-aluminium chloride complexes, XC6H4 COCl·AlCl3 in methylene chloride at 0-20° to form the corresponding ketones XC6H4CO(CC)nSiMe3 in excellent (n = 1) or moderate (n = 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC6H4CO(CC)nH. The method provides the first practical route to the ketotetraynes (n = 4) and usefully supplements existing oxidative methods for keto-monoyne and -diyne synthesis. The oxalyl chloride-aluminium chloride complex reacts with Me3SiCCSiMe3 to give the novel silyl-substituted heterocycle (I): {A figure is presented}.