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
• Article Data: 30

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

Description

Tris(4-methylphenyl)phosphine, also known as TMPP, is an organophosphorus compound that serves as a ligand in coordination chemistry. It is a white to off-white crystalline solid, soluble in common organic solvents, and is known for its strong electron-donating properties. This makes it a versatile chemical reagent with applications in various fields of organic and inorganic chemistry.

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

• 63692-06-8 {AgCl(C₂₁H₂₁P)2} 
• 61249-11-4 {HP(p-tol)3}⁽¹⁺⁾ 
• 29115-48-8 [AgCl(tri(p-tolyl)phosphine)3] 
• 136129-66-3 bis{copper(I)(dithiouracil)(tri-p-tolylphosphine)chloride} 
• 136129-68-5 bis{copper(I)(thiourea)(tri-p-tolylphosphine)chloride} 
• 106-43-4 para-chlorotoluene 
• 105071-37-2 tris(p-tolyl)phosphine borane complex 
• 1017-60-3 di-p-tolylphosphine 
• 106-38-7 para-bromotoluene 
• 21859-00-7 tri(p-tolyl)phosphine dichloride 
• 797-70-6 tri(4-methylphenyl)phosphine oxide 
• 2637-34-5 pyridine-2-thione 
• 29115-46-6 {Ag(P(p-C₆H₄CH₃)3)4}{ClO₄} 
• 38845-39-5 {AgNO₃(C₂₁H₂₁P)2} 

Downstream Products

• 95867-03-1 tris-(4-methyl-3-nitro-phenyl)-phosphine oxide 
• 607-01-2 ethyl-diphenyl-phosphane 
• 52500-74-0 Fe(CO)3(P(C₆H₄CH₃)3)2 
• 71667-38-4 tetrakis(tris(4-methyl)phenyl)phosphinenickel 
• 52729-09-6 (CO)3NiP(C₆H₄CH₃-p)3 
• 52553-46-5 {Fe(CO)4P(p-C₆H₄CH₃)3} 
• 153588-67-1 tricarbonylchlorobis(tri-p-tolylphosphine)rhenium 
• 118400-47-8 Co₂(CO)6{P(p-tol)3}2 
• 118400-43-4 Co(CO)3{P(p-tol)3}2 
• 14319-11-0 NiBr₂(Tri-p-tolyl-phosphin)2 
• 14319-12-1 NiI₂(Tri-p-tolyl-phosphin)2 
• 855007-22-6 Co(P(C₆H₄CH₃)3)(CO)3(C(O)CH₃) 
• 634902-99-1 [Ag(diacetonamine)(P(C₆H₄Me-4)3)]perchlorate 
• 77061-42-8 CdI₂(P(p-CH₃C₆H₄)3)2 

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.

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.