1777-56-6

Basic information

• Product Name: 1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone
• CAS NO: 1777-56-6
• Molecular Formula: C₂₆H₂₀ClOP
• Molecular Weight: 414.8632
• Mol File: 1777-56-6.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 581°C at 760 mmHg
• Flash Point: 305.2°C
• Density: 1.25g/cm³
• Vapor Pressure: 1.71E-13mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone(1777-56-6)
• EPA Substance Registry System: 1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone(1777-56-6)

Safety Data

• Hazardous Substances Data: 1777-56-6(Hazardous Substances Data)

Usage

General Description

1-(4-chlorophenyl)-2-(triphenyl-lambda5-phosphanylidene)ethanone, also known as chlorodiphenylphosphine ketone, is an organophosphorus compound with the molecular formula C20H15ClOP. It is a yellow to orange solid that is commonly used in organic synthesis and as a ligand in transition metal catalysis. The compound contains a chlorophenyl group and a triphenylphosphine group attached to a ketone group, giving it unique reactivity and potential applications in various chemical processes. It is important to handle and store this compound with care, as it poses potential health and environmental hazards due to its toxic and flammable properties.

Upstream product

• 59956-67-1 4-chlorobenzyl 2-bromoacetate 
• 603-35-0 triphenylphosphine 
• 99-91-2 para-chloroacetophenone 
• 825-40-1 2-bromo-p-chloroacetophenone 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Downstream Products

• 4953-95-1 N-(2-methylphenyl)cyanothioformanilide 
• 6616-22-4 [2-(4-Chloro-phenyl)-1-methyl-2-oxo-ethyl]-triphenyl-phosphonium; iodide 
• 23336-93-8 (Z)-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one 
• 183947-04-8 (E)-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one 
• 791-28-6 Triphenylphosphine oxide 
• 288072-76-4 5-(4-Chloro-phenyl)-2-[2-(4-chloro-phenyl)-2-oxo-eth-(E)-ylidene]-furan-3-one 
• 2689-81-8 (4-chlorophenacyl)triphenylphosphonium bromide 
• 7448-87-5 p-chlorophenyl vinyl ketone 
• 67382-44-9 p-Chlor-1-pentyliden-acetophenon 
• 1042769-33-4 [(Ph₃PCHCOC₆H₄-4-Cl)mercury(II)dichloride]2 
• 1042769-32-3 [(Ph₃PCHCOC₆H₄-4-Cl)mercury(II)dibromide]2 
• 1042769-31-2 [(Ph₃PCHCOC₆H₄-4-Cl)mercury(II)dichloride]2 
• 1256284-91-9 1-(4-chlorophenyl)-2-(9-methyl-2,3,4,9-tetrahydro-1H-carbazol-4-yl)ethanone 
• 1612794-34-9 C₁₈H₁₃ClO₂ 

Relevant articles and documents

Synthesis and characterisation of Hg (II) and Ag (I) complexes of 4-fluorobenzoylmethylenetriphenylphosphorane and 4-chlorobenzoyl methylenetriphenylphosphorane, with spectroscopic studies

4-flourobenzyloxymethylenetriphenylphosphorane ylide [Ph 3PCHCOC6H4F], (FBPPY), and 4- chlorobenzyloxymethylenetriphenylphosphorane ylide [Ph3PCHCOC 6H4Cl](CBPPY), have been synthesised. Th

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Rh(iii)-catalyzed diastereoselective cascade annulation of enone-tethered cyclohexadienonesviaC(sp2)-H bond activation

Herein, we report highly diastereoselective arylative cyclization of enone-tethered cyclohexadienonesviaRh(iii)-catalyzed C-H activation ofN-methoxybenzamides. This reaction proceeds through the formation of a five-membered rhodacycle followed by bis-Michael cascade annulation to access functionalized bicyclic scaffolds with four contiguous stereocenters with a broad substrate scope. These products have excellent functional handles, allowing further synthetic transformation to increase the structural complexity. Furthermore, mechanistic studies of arylative cyclization and a gram-scale experiment are also presented.