2129-31-9

Basic information

• Product Name: 4-(DIPHENYLPHOSPHINO)BENZOIC ACID
• Synonyms: 4-(DIPHENYLPHOSPHINO)BENZOIC ACID;Diphenyl(p-carboxyphenyl) phosphine;p-(Diphenylphosphino)benzoic acid;(4-Carboxyphenyl)diphenylphosphine;4-(Diphenylphosphino)benzoic acid 97%;4-di(phenyl)phosphanylbenzoic acid;4-Diphenylphosphanyl-benzoesaeure
• CAS NO: 2129-31-9
• Molecular Formula: C₁₉H₁₅O₂P
• Molecular Weight: 306.29
• Product Categories: Phosphine Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds
• Mol File: 2129-31-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 157-160 °C(lit.)
• Boiling Point: 448°C at 760 mmHg
• Flash Point: 224.7°C
• Appearance: White to yellow/Crystalline Powder
• Vapor Pressure: 8.24E-09mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.01±0.10(Predicted)
• CAS DataBase Reference: 4-(DIPHENYLPHOSPHINO)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIPHENYLPHOSPHINO)BENZOIC ACID(2129-31-9)
• EPA Substance Registry System: 4-(DIPHENYLPHOSPHINO)BENZOIC ACID(2129-31-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2129-31-9(Hazardous Substances Data)

Usage

General Description

4-(Diphenylphosphino)benzoic acid is a chemical compound that is categorized as an organophosphorus compound. It is mainly used as a ligand in the field of inorganic chemistry in the creation of catalysts through a coordination of metal complex bonding. Known to be soluble in water, the chemical exhibits a white crystalline powder physical state. 4-(DIPHENYLPHOSPHINO)BENZOIC ACID is known for its acyl transfer catalysis property, which is crucial in reactions in both biological and synthetic processes. The compound's composition includes elements such as carbon, hydrogen, oxygen, and phosphorus.

InChI:InChI=1/C19H15O2P/c20-19(21)15-11-13-18(14-12-15)22(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14H,(H,20,21)

Upstream product

• 124-38-9 carbon dioxide 
• 734-59-8 (4-bromophenyl)diphenylphosphane 
• 5032-51-9 methyl 4-(diphenylphosphino)benzoate 
• 17763-71-2 4-carbomethoxyphenyl triflate 
• 586-76-5 4-Bromobenzoic acid 
• 829-85-6 diphenylphosphane 
• 403-33-8 methyl 4-flurobenzoate 
• 1194-02-1 4-fluorobenzonitrile 
• 4762-31-6 4-Bromphenylphosphindichlorid 
• 1079-66-9 chloro-diphenylphosphine 
• 623-00-7 4-bromobenzenecarbonitrile 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 5032-55-3 (4-methoxycarbonylphenyl)diphenylphosphine oxide 
• 52509-80-5 p-F-C₆H₄COOK 

Downstream Products

• 111767-82-9 (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde 
• 147999-76-6 [(4-benzoic acid-diphenylphosphane)-gold(I)-chloride] 
• 174585-24-1 dichlorobis[(4-carboxyphenyl)diphenylphosphine]platinum(II) 
• 955095-23-5 3,5-bis(docosyloxy)benzyl 4-(diphenylphosphino)benzoate 
• 566180-43-6 C₃₈H₃₀Cl₂O₄P₂Pd 
• 1429125-53-0 N-benzyl-4-(diphenylphosphino)benzamide 
• 1266603-41-1 [(C₆H₅)2PC₆H₄CONHC₆H₃C₂NH(CH₃)]2CH(C₂H₅) 

Relevant articles and documents

Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine

A simple synthetic method of triarylphosphine compounds by KOH-promoted P-Arylation reaction of aryl halides with diphenylphosphine is presented. Notably, this transformation could smoothly proceed with high yields under transition-metal-free and mild reaction conditions. In addition, this protocol is valuable for industrial application due to the convenient operation and readily accessible aromatic halides. A possible explanation of the reaction mechanism was proposed based on the experimental data.

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 %).

A rhodium triphenylphosphine catalyst for alkene hydrogenation supported on neat superparamagnetic iron oxide nanoparticles

A phosphonic acid functionalized triphenylphosphine rhodium complex was synthesized and grafted onto neat superparamagnetic iron oxide nanoparticles. The material was investigated by elemental analysis, IR spectroscopy, thermogravimetric analysis, XRD, N2-physisorption analyses, and TEM measurements. The obtained hybrid material could be used as a catalyst for the hydrogenation of alkenes with excellent yields and a broad substrate scope. The catalyst can be reused ten times without any loss of activity. According to the results from X-ray absorption spectroscopy, it is likely that formation of Rh nanoparticles occurs during the reaction.