1159-54-2

Usage

Uses

Used in Pharmaceutical Industry:
TRIS(4-CHLOROPHENYL)PHOSPHINE is used as a catalyst for the preparation of chromans and (E,E)-1,3-dienes via the reaction of γ-substituted allenoates with aldehydes. This application is crucial in the synthesis of various pharmaceutical compounds and intermediates.
Used in Chemical Synthesis:
TRIS(4-CHLOROPHENYL)PHOSPHINE is used as a catalyst in solvent-free Heck reactions, which are important for the synthesis of various organic compounds and materials.
Used in Organic Chemistry:
TRIS(4-CHLOROPHENYL)PHOSPHINE is used as a co-catalyst in the regioselective carbomagnesiation of terminal alkynes and enynes with alkyl Grignard reagents. This application is essential for the selective synthesis of specific organic compounds.
Used in Coordination Chemistry:
TRIS(4-CHLOROPHENYL)PHOSPHINE is used as a co-catalyst in rhodium-catalyzed coordination-assisted regioselective alkenylation of aromatic C-H bonds with terminal silylacetylenes. This application is vital for the selective functionalization of aromatic compounds.
Used in Hydrogenation Reactions:
TRIS(4-CHLOROPHENYL)PHOSPHINE is used as a co-catalyst in rhodium-catalyzed hydrogenation reactions, which are important for the reduction of various functional groups in organic compounds.
Used in Allylation Reactions:
TRIS(4-CHLOROPHENYL)PHOSPHINE is used as a co-catalyst in platinum-catalyzed allylation reactions, which are crucial for the formation of carbon-carbon bonds in organic synthesis.

InChI:InChI=1/C18H12Cl3P/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18/h1-12H

Upstream product

• 150766-93-1 (4-chlorophenyl)zinc(II) bromide 
• 4576-56-1 tris(p-chlorophenyl)phosphine oxide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 119821-90-8 (2-quinaldinate)(carbonyl)(P(4-Cl-C₅H₄)3)2rhodium(I) 
• 119821-90-8 (2-quinaldinate)(carbonyl)(P(4-Cl-C₅H₄)3)2rhodium(I) 
• 106-39-8 bromochlorobenzene 
• 7270-47-5 4-chlorophenylmagnesium iodide 

Downstream Products

• 4576-56-1 tris(p-chlorophenyl)phosphine oxide 
• 15676-97-8 Tris-(4-chlor-phenyl)-ethoxy-carbonylmethylen-phosphoran-hydrobromid 
• 14796-92-0 N-phenyl-P,P,P-tris(p-chlorophenyl)phospha-λ⁵-azene 
• 7293-72-3 Tris-(p-chlorphenyl)-fluorenyl-⁽⁹⁾-phosphonium-bromid 
• 16812-36-5 cumyloxy radical 
• 5032-62-2 tris-p-chlorophenylphosphine sulphide 
• 52151-06-1 (CO)3NiP(C₆H₄Cl-p)3 
• 146645-28-5 trimesityliridium(III) 
• 126347-08-8 {1,5-(p-ClC₆H₄)3PN}2S₄N₄ 
• 21038-94-8 cis-{(C₂H₅)4N}{(CO)4Cr{P(C₆H₄Cl-p)3}Cl} 

Relevant academic research and scientific papers

Novel functionalized microporous organic networks based on triphenylphosphine

This article describes the synthesis and functions of phosphine or phosphine oxide functionalized networks (PP-P or PP-PO; PP=porous polymer). These materials were predominantly microporous and exhibited high surface areas (SBET: 1284 and 1353 m2 g-1 for PP-P and PP-PO, respectively), with high CO2 (2.46 and 3.83 mmol g-1 for PP-P and PP-PO, respectively) uptake capacities. Pd nanoparticles can be simply incorporated into the functionalized networks (PP-P-Pd or PP-PO-Pd) through a facile one-step impregnation. A yield of 98 % was obtained in the Suzuki reaction between 1-chlorobenzene and p-tolylboronic acid with the PP-P-Pd system, which was higher than that obtained when PP-PO-Pd (53.2 %) or [Pd(PPh3)4] (38.2 %) was used as the catalyst. The superior catalytic ability of PP-P-Pd can be attributed to the structural features that incorporate triarylphosphine within a microporous structure. Phosphine sponges: Microporous polymers (see figure) with phosphine or phosphine oxide as connecting nodes were prepared. These materials exhibit high surface areas and excellent carbon dioxide capture capacities. Pd nanoparticles supported on the polymeric networks were also prepared; they exhibit high catalytic activity for Suzuki reactions. Copyright

Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P4) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.

Organic super-long room-temperature phosphorescent material as well as preparation method and application thereof

The invention discloses an organic super-long room-temperature phosphorescent material and a preparation method and an application thereof, the organic super-long room-temperature phosphorescent material is a color-adjustable organic room-temperature phosphorescent material with excitation wavelength dependence and thermochromism performance simultaneously, and substituent-Cl is introduced to para-position and meta-position of triphenylphosphine oxide respectively, and the series of compounds are prepared; the afterglow luminescence color of the materials can be adjusted by controlling the wavelength of an excitation light source and the temperature of the environment; in combination with the adjustable performance of different colors, the application of information anti-counterfeiting and visual temperature detection is realized at the same time.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

Synthesis method of phosphine (III) compound

The invention aims to provide an aryl phosphine oxide compound as a raw material, wherein P=O keys are activated by an acid anhydride and alkali is continued. The preparation of the phosphine (III) compound is carried out under the action of a crown ether and a reducing agent. The method has the advantages of cheap and easily available raw materials, simple operation, high atomic economy and the like. Compared with a traditional reduction mode, the method is ingenious in design, waste emission is reduced, separation of intermediate products is omitted, and related reagents such as silicon hydrogen, aluminum, boron and the like with higher price can be avoided. And the reaction suitability is extensive.

Atom Economic Ruthenium-Catalyzed Synthesis of Bulky β-Oxo Esters

Ruthenium complexes with the formulae Ru(CO)2(PR3)2(O2CPh)2 [6a-h; R=n-Bu, p-MeO-C6H4, p-Me-C6H4, Ph, p-Cl-C6H4, m-Cl-C6H4, p-CF3-C6H4, m,m′-(CF3)2C6H3] were prepared by treatment of triruthenium dodecacarbonyl [Ru3(CO)12] with the respective phosphine and benzoic acid or by the conversion of Ru(CO)3(PR3)2 (8e-h) with benzoic acid. During the preparation of 8, ruthenium hydride complexes of type Ru(CO)(PR3)3(H)2 (9g, h) could be isolated as side products. The molecular structures of the newly synthesized complexes in the solid state are discussed. Compounds 6a-h were found to be highly effective catalysts in the addition of carboxylic acids to propargylic alcohols to give valuable β-oxo esters. The catalyst screening revealed a considerably influence of the phosphine′s electronic nature on the resulting activities. The best performances were obtained with complexes 6g and 6h, featuring electron-withdrawing phosphine ligands. Additionally, catalyst 6g is very active in the conversion of sterically demanding substrates, leading to a broad substrate scope. The catalytic preparation of simple as well as challenging substrates succeeds with catalyst 6g in yields that often exceed those of established literature systems. Furthermore, the reactions can be carried out with catalyst loadings down to 0.1mol% and reaction temperatures down to 50 C.

Highly efficient reduction of tertiary phosphine oxides and sulfides with amine-assisted aluminum hydrides under mild conditions

Reduction of tertiary phosphine oxides and sulfides into the corresponding phosphines with amine-assisted aluminum hydrides has been studied. The method is characterized by mild conditions, short reaction time, high efficiency, and expanded substrate scope. The new method is an alternative to the currently used methods of reducing phosphine oxides or recycling phosphines engaged in organic reactions.

Metal-free reduction of tertiary phosphine oxides with Hantzsch ester

The (COCl)2/Hantzsch ester is found to be an effective system for the metal-free reduction of tertiary phosphine oxides. The reaction proceeds under mild conditions, and is applicable to triarylphosphine oxides and alkyldiarylphosphine oxides to produce the corresponding tertiary phosphines in good to excellent yields. This new finding provides a practical, convenient and metal-free method for the reduction of tertiary phosphine oxides to tertiary phosphines, and shows potential application in organic synthesis.

Novel functional organic network containing quaternary phosphonium and tertiary phosphorus

A quaternary phosphonium and tertiary phosphorus functionalized microporous polymer was obtained via nickel(0)-catalyzed Yamamoto-type cross-coupling reaction. The integration ratio of signals (quaternary phosphonium to tertiary phosphorus atoms) was close to 3:2. The polymer networks were stable toward water, base, and acid, and indeed no change in surface area was observed even after the material was treated with 10 M HCl. The pore size distribution calculated by the Horvath-Kawazoe method indicated the presence of micropores with a mean width of about 0.7 and 1.4 nm. Their apparent BET specific surface areas can be tuned (from 650 to 980 m2 g-1) by changing the counteranions (Br- to F-). It displays high intrinsic catalytic activity for the reaction between epoxide and CO2 (yield: 98%, 1 atm). Pd nanoparticles supported on the polymer networks were also prepared, which exhibits high catalytic activity for cross-coupling reaction between 1-chlorobenzene and phenylboronic acid (yield: >95.8%).