5032-55-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
Benzoic acid, 4-(diphenylphosphinyl)-, methyl ester is used as an intermediate in the synthesis of various pharmaceutical and agrochemical products. Its unique structure and reactivity make it a valuable building block for the development of new drugs and pesticides.
Used in Organometallic Chemistry and Catalysis:
As a ligand, benzoic acid, 4-(diphenylphosphinyl)-, methyl ester plays a crucial role in organometallic chemistry and catalysis. Its ability to form stable complexes with metal ions enhances the catalytic activity and selectivity of various chemical reactions, making it an essential component in the development of new catalysts and catalytic processes.
Used in Antimicrobial and Antifungal Applications:
Benzoic acid, 4-(diphenylphosphinyl)-, methyl ester has been studied for its potential antimicrobial and antifungal properties. Its ability to inhibit the growth of various microorganisms makes it a promising candidate for use in the development of new antimicrobial and antifungal agents, particularly in the context of increasing antibiotic resistance.
Used in Industrial Applications:
The versatility of benzoic acid, 4-(diphenylphosphinyl)-, methyl ester extends to various industrial applications. Its unique chemical properties and reactivity make it suitable for use in the development of new materials, coatings, and other industrial products, contributing to the advancement of various industries.

Upstream product

• 4559-70-0 Diphenylphosphine oxide 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 619-44-3 methyl 4-iodobenzoate 
• 41605-53-2 methyl 4-[(nonafluorobutanesulfonyl)oxy]benzoate 
• 6725-72-0 4-methoxycarbonylbenzoic acid phenyl ester 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 51207-43-3 methyl 4-(tosyloxy)benzoate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 5525-40-6 (4-bromophenyl)diphenylphosphine oxide 
• 17763-71-2 4-carbomethoxyphenyl triflate 
• 829-85-6 diphenylphosphane 

Downstream Products

• 1257322-25-0 methyl 4-(diphenylphosphanyl)benzoate borane 
• 2129-31-9 4-diphenylphosphanobenzoic acid 
• 5032-51-9 methyl 4-(diphenylphosphino)benzoate 
• 78952-89-3 p-(diphenylphosphino) benzoic acid hydrazide 

Relevant academic research and scientific papers

Visible-Light-Induced Nickel-Catalyzed P(O)-C(sp2) Coupling Using Thioxanthen-9-one as a Photoredox Catalysis

An efficient method has been developed for photocatalytic P(O)-C(sp2) coupling of (hetero)aryl halides with H-phosphine oxides or H-phosphites under the irradiation of visible light or sunlight. The thioxanthen-9-one/nickel dual catalysis mediates this ph

Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide

An iodide-accelerated, palladium-catalyzed C-P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C-P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

NiCl 2as a Cheap and Efficient Precatalyst for the Coupling of Aryl Fluorosulfonate and Phosphite/Phosphine Oxide

Herein, NiCl 2is employed as a cheap precatalyst in the formation of C(sp 2)-P bond via cross-coupling reaction of phenol derivatives and phosphine oxides/phosphites. This catalytic system allows a variety of phenols with diverse functional groups to transform into phosphates with good yields. No additional additive is used in this reaction.

Visible-light-mediated semi-heterogeneous black TiO2/nickel dual catalytic C (sp2)-P bond formation toward aryl phosphonates

The combination of black TiO2 nanoparticles (NPs) with a nickel catalyst provides a low-cost, sustainable, and reusable alternative dual catalytic system to a homogeneous counterpart (noble metals). This black TiO2-photoredox/nickel dual catalytic system has efficiently driven C-P bond formation between aryl iodides and diarylphosphine oxides under visible light, providing good to excellent yields as well as tolerating a variety of functional groups. The practical application of this semi-heterogeneous protocol has been highlighted by a sunlight experiment, a gram-scale reaction, and a reusability test.

Palladium-Catalyzed C-P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides

An efficient procedure for C-P bond formation via the palladium-catalyzed [Pd(OAc) 2 /dppf/Cs 2 CO 3 ] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc) 2 /dippf/ t -BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds

Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.

Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides

We present a novel and highly efficient methodology that allows for the construction of C-P bonds via the palladium-catalyzed air-based oxidative coupling of various commercially available arylboronic acids with easily oxidized H-phosphine oxides leading to valuable aryl phosphine oxides, particularly triarylphosphine oxides, with the use of air as the green oxidant, broad substrate applicability and good to excellent yields. The described catalytic system should be an efficient complement to the Chan-Lam type reaction and be useful in synthetic programs. This journal is the Partner Organisations 2014.

Nickel-catalyzed C-P cross-coupling of arylboronic acids with P(O)H compounds

A novel and efficient Ni-catalyzed coupling of a wide range of arylboronic acids with H-phosphites, H-phosphinate esters, and H-phosphine oxides has been developed, providing a general and powerful tool for the synthesis of various aryl-phosphorus compounds, especially for valuable triarylphosphine oxides, in good to excellent yield. This protocol is the first Ni-catalyzed C-P bond-forming reaction between arylboronic acids and P(O)H compounds.

[NiCl2(dppp)]-catalyzed cross-coupling of aryl halides with dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphine

We present a general approach to C-P bond formation through the cross-coupling of aryl halides with a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane by using [NiCl2(dppp)] as catalyst (dppp=1,3-bis(diphenylphosphino)propane). This catalyst system displays a broad applicability that is capable of catalyzing the cross-coupling of aryl bromides, particularly a range of unreactive aryl chlorides, with various types of phosphorus substrates, such as a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane. Consequently, the synthesis of valuable phosphonates, phosphine oxides, and phosphanes can be achieved with one catalyst system. Moreover, the reaction proceeds not only at a much lower temperature (100-120 °C) relative to the classic Arbuzov reaction (ca. 160-220 °C), but also without the need of external reductants and supporting ligands. In addition, owing to the relatively mild reaction conditions, a range of labile groups, such as ether, ester, ketone, and cyano groups, are tolerated. Finally, a brief mechanistic study revealed that by using [NiCl2(dppp)] as a catalyst, the NiII center could be readily reduced in situ to Ni0 by the phosphorus substrates due to the influence of the dppp ligand, thereby facilitating the oxidative addition of aryl halides to a Ni0 center. This step is the key to bringing the reaction into the catalytic cycle. Making bonds: C-P bonds were formed by the Ni-catalyzed cross-coupling of aryl halides and phosphorus substrates without the need of external reductants. Aryl bromides and less reactive aryl chlorides underwent smooth coupling with several different phosphorus substrates to afford phosphonates, phosphine oxides, and phosphines (see scheme; dppp=1,3-bis(diphenylphosphino)propane). Due to the mild reaction conditions, a range of labile groups, such as ether, ester, ketone, and cyano groups, are tolerated. Copyright

Nickel-catalyzed C-P coupling of aryl mesylates and tosylates with H(O)PR1R2

A method was developed for the nickel-catalyzed phosphonylation of aryl mesylates and tosylates with H(O)PR1R2. To the best of our knowledge, this is the first example of nickel-catalyzed C-P coupling of aryl mesylates and tosylates. Most of the substrates gave moderate to good yields under our catalytic system.