218281-19-7

Basic information

• Product Name: Tris(4-methylphenyl)phosphine
• CAS NO: 218281-19-7
• Molecular Formula: C21H21P
• Molecular Weight: 304.365201
• Mol File: 218281-19-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Tris(4-methylphenyl)phosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(4-methylphenyl)phosphine(218281-19-7)
• EPA Substance Registry System: Tris(4-methylphenyl)phosphine(218281-19-7)

Safety Data

• Hazardous Substances Data: 218281-19-7(Hazardous Substances Data)

Usage

Uses

Used in Catalysis:
Tris(4-methylphenyl)phosphine is used as a ligand in catalysis for its ability to facilitate various chemical reactions and syntheses. Its strong electron-donating properties make it a valuable component in the development of catalysts that can enhance reaction rates and selectivity.
Used in Stabilizing Metal Nanoparticles:
TMPP is used as a stabilizer for metal nanoparticles, which is crucial in preventing the aggregation and degradation of these particles. This application is particularly important in industries where metal nanoparticles are used for their unique properties, such as in catalysis, electronics, and medicine.
Used in Pharmaceutical Production:
Tris(4-methylphenyl)phosphine is used in the production of pharmaceuticals, where its coordination chemistry properties can be leveraged to create new drug molecules or improve the synthesis of existing ones. Its ability to interact with metal ions can be particularly useful in the development of metal-based drugs or drug delivery systems.
Used in Agrochemical Production:
TMPP is also utilized in the production of agrochemicals, where its coordination chemistry can be applied to develop new pesticides, herbicides, or fertilizers. Its strong electron-donating properties can be beneficial in the synthesis of these compounds, potentially leading to more effective and environmentally friendly products.

Upstream product

• 106-38-7 para-bromotoluene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 696-61-7 4-tolylmagnesium chloride 
• 2417-95-0 p-tolyllithium 
• 603-35-0 triphenylphosphine 
• 64-19-7 acetic acid 
• 126403-71-2 p-tolylzinc bromide 
• 6372-42-5 cyclohexyldiphenylphosphine 
• 1486-28-8 diphenyl(methyl)phosphine 
• 607-01-2 ethyl-diphenyl-phosphane 
• 63692-06-8 {AgCl(C₂₁H₂₁P)2} 
• 52500-74-0 tricarbonyl bis(tri-p-tolylphosphine) iron 
• 201230-82-2 carbon monoxide 

Downstream Products

• 14650-27-2 benzyl-tri-p-tolyl-phosphonium; chloride 
• 120857-50-3 hexa-P-p-tolyl-P,P'-pentanediyl-di-phosphonium; dibromide 
• 20676-74-8 tris(4-methylphenyl)phenylphosphonium iodide 
• 13904-27-3 N-(tri-p-tolyl-phosphoranylidene)-toluene-4-sulfonamide 
• 112368-29-3 tetrakis(4-methylphenyl)phosphonium iodide, 
• 1896-61-3 methyl-tris(p-toluylphenyl)phosphonium iodide 
• 95867-03-1 tris-(4-methyl-3-nitro-phenyl)-phosphine oxide 
• 63232-54-2 (Methoxycarbonylamino-methyl)-tri-p-tolyl-phosphonium; chloride 
• 852-89-1 tri-p-tolylethylphosphonium bromide 
• 60271-49-0 [4-(2-benzothiazol-2-yl-vinyl)-benzyl]-tri-p-tolyl-phosphonium; bromide 
• 62779-24-2 (Ethoxycarbonylamino-methyl)-tri-p-tolyl-phosphonium; chloride 
• 42079-98-1 (E)-1-methyl-4-(oct-1-en-1-yl)benzene 
• 42079-96-9 1-(p-Methylphenyl)-octen-2 
• 62779-13-9 Isocyanatomethyl-tri-p-tolyl-phosphonium; chloride 

Relevant articles and documents

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.

Palladium-Catalyzed Diastereoselective Synthesis of (Z)-Conjugated Enynyl Homoallylic Alcohols

The diastereoselective synthesis of anti-homoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described. This reaction features a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. In this reaction, Pd(0) functions as a catalyst in two fundamental steps of the tandem sequence: 1) the generation of a borylated π-allylpalladium species from bifunctional conjunctive reagents, inducing umpolung allylation of aldehydes, and 2) C(sp2)?C(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility. (Figure presented.).

Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines

Palladium-catalyzed C-P bond formation reaction of ArBr/ArOTf using acylphosphines as differential phosphination reagents is reported. The acylphosphines show practicable reactivity with ArBr and ArOTf as the phosphination reagents, though they are inert to the air and moisture. The reaction affords trivalent phosphines directly in good yields with a broad substrate scope and functional group tolerance. This reaction discloses the acylphosphines' capability as new phosphorus sources for the direct synthesis of trivalent phosphines.

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.

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.

Synthesis method of triphenylphosphine derivative tri-(R-phenyl) phosphine

The invention relates to a synthesis method of a triphenylphosphine derivative tri-(R-phenyl) phosphine. The synthesis method comprises the following steps: adding magnesium chips, a solvent and R-substituted halobenzene into a reaction kettle under the protection of nitrogen, initiating a reaction at a proper temperature, and dropwise adding an R-substituted halobenzene solution to synthesize anintermediate; dropwise adding a phosphorus trichloride solution to complete a Grignard reaction; dropwise adding diluted hydrochloric acid for hydrolysis after negative-pressure desolvation; and carrying out post-treatment to obtain TRPP. According to the method, the tri-(R-phenyl) phosphine of which the purity is greater than 99% is obtained with high selectivity and high yield.

Superbase-Assisted Selective Synthesis of Triarylphosphines from Aryl Halides and Red Phosphorus: Three Consecutive Different SNAr Reactions in One Pot

Aryl halides, ArX (Ar = Ph, 2-, 3- and 4-Tol, 1- and 2-Np, 4-C6H4CONH2; X = F, Cl, Br), rapidly and exothermically (100–180 °C, 0.5–2 h) react with red phosphorus in superbase systems KOH/L, where L is a polar nonhydroxylic complexing solvent (ligand), such as NMP, DMSO, HMPA, to afford the corresponding triarylphosphines (Ar3P) in up to 74 % yield (for X = F). Thus, three consecutive reactions of SNAr (aromatic nucleophilic substitution) to form the three C(sp2)–P bonds are realized in one pot. The synthesis is mostly chemoselective (with rare exception): neither mono- nor diphosphines have been isolated. The best results were attained when aryl fluorides were treated with red phosphorus (Pn) in the KOH/NMP superbase system. This environmentally friendly, PCl3-free synthesis of Ar3P from available starting materials opens an easy and straightforward access to triarylphosphines, which are important ligands, synthetic auxiliaries, and components of high-tech- and medicinally oriented complexes.

Synthesis, gallium-68 radiolabelling and biological evaluation of a series of triarylphosphonium-functionalized DO3A chelators

Radiolabelled lipophilic cations that accumulate in mitochondria according to the magnitude of the mitochondrial membrane potential can be used to report non-invasively on mitochondrial dysfunction in cardiovascular disease, cardiotoxicity, and cancer. While several such cations are already commercially available for SPECT imaging, PET offers greater promise in terms of sensitivity, resolution, and capacity for dynamic imaging and pharmacokinetic modelling. We have therefore synthesised a series of three triarylphosphonium-functionalised DO3A chelators for positron emitter gallium-68, with differing alkyl-functionalisation motifs to provide opportunities for tunable lipophilicity as a means of optimising their pharmacokinetics. To assess their capacity to report on mitochondrial membrane potential, we assessed their pharmacokinetic profiles in isolated tumour cells and isolated perfused rat hearts before and after mitochondrial depolarisation with the ionophore CCCP. All three compounds radiolabelled with over 97% RCY and exhibited log?D values of between ?3.12 and ?1.81. In vitro assessment of the uptake of the radiotracers in cultured tumour cells showed a three-fold increase in uptake compared to unchelated [68Ga]Ga(iii). However, each complex exhibited less than 1% retention in healthy hearts, which was not significantly diminished by mitochondrial depolarisation with CCCP. This preliminary work suggests that while this approach is promising, the lipophilicity of this class of tracers must be increased in order for them to be useful as cardiac or cancer imaging agents.

Electrophilic Phosphonium Cation-Mediated Phosphane Oxide Reduction Using Oxalyl Chloride and Hydrogen

The metal-free reduction of phosphane oxides with molecular hydrogen (H2) using oxalyl chloride as activating agent was achieved. Quantum-mechanical investigations support the heterolytic splitting of H2 by the in situ formed electrophilic phosphonium cation (EPC) and phosphane oxide and subsequent barrierless conversion to the phosphane and HCl. The reaction can also be catalyzed by the frustrated Lewis pair (FLP) consisting of B(2,6-F2C6H3)3 and 2,6-lutidine or phosphane oxide as Lewis base. This novel reduction was demonstrated for triaryl and diaryl phosphane oxides providing access to phosphanes in good to excellent yields (51–93 %).

Mild Reduction of Phosphine Oxides with Phosphites To Access Phosphines

A new method for the iodine-catalyzed reduction of phosphine oxides with phosphites at room temperature is reported. The mild reaction conditions, scalability, and simple purification requirements render it a method of choice for the large-scale production and facile regeneration of a variety of phosphines. Mechanistic studies, supported by DFT calculations of the oxygen transfer between the starting phosphine oxide and the phosphite reagent, are also presented. Such transmutations of phosphorus species were previously unknown.