2959-74-2

Usage

Uses

Used in Organometallic Chemistry:
Benzyl(diphenyl)phosphane oxide is used as a ligand for the formation of stable complexes with transition metals. Its application in this field is crucial for enhancing the efficiency and selectivity of catalytic reactions.
Used in Homogeneous Catalysis:
BDPO serves as a ligand in homogeneous catalysis, where it contributes to the uniform distribution of catalysts in a reaction mixture, thereby improving the reaction rate and selectivity.
Used as a Chiral Auxiliary in Asymmetric Catalysis:
In asymmetric catalysis, benzyl(diphenyl)phosphane oxide is utilized as a chiral auxiliary. This role is pivotal for inducing enantioselectivity in chemical reactions, leading to the preferential formation of one enantiomer over another.
Used in Industrial Processes:
BDPO finds applications in several industrial processes, where its unique properties as a ligand and its ability to form stable complexes are harnessed to improve the efficiency of chemical transformations.
Used as a Reagent in Laboratory Research:
Benzyl(diphenyl)phosphane oxide is a valuable reagent in laboratory research, where it is employed to explore new catalytic systems and to understand the underlying mechanisms of various chemical reactions.
Used as an Intermediate in Organic Synthesis:
BDPO is also a useful intermediate in the synthesis of other organic compounds, where it can be further modified or incorporated into more complex molecular structures for specialized applications.

Upstream product

• 119-61-9 benzophenone 
• 118214-15-6 Lithium(I)- 
• 111-71-7 heptanal 
• 33417-25-3 Benzylbenzylidendiphenylphosphoran 
• 7751-69-1 α-chlorobenzyl(diphenyl)phosphine oxide 
• 719-80-2 Ethyl diphenylphosphinite 
• 100-39-0 benzyl bromide 
• 137789-93-6 diethylaluminum diphenylphosphinite 
• 33845-83-9 benzyl(chloro)diphenylphosphonium chloride 
• 100-52-7 benzaldehyde 
• 1079-65-8 Bromodiphenylphosphin 
• 100-44-7 benzyl chloride 
• 1499-21-4 Diphenylphosphinic chloride 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 5097-93-8 trans-4-styrylpyride 
• 2633-06-9 (E)-3-(2-phenylvinyl)pyridine 
• 21310-05-4 diphenyl-(1-phenyl-propyl)-phosphine oxide 
• 58-72-0 Triphenylethylene 
• 76202-75-0 (α-Benzoylbenzyl)diphenylphosphanoxid 
• 1707-03-5 diphenyl-phosphinic acid 
• 99997-34-9 diphenylphosphinoyl-phenyl-acetic acid 
• 122631-93-0 di(m-nitrophenyl)-p-nitrobenzylphosphine oxide 
• 833-81-8 (E)-1,2-diphenylpropene 
• 56253-64-6 (2-methyl-1-butenyl)-benzene 
• 100086-68-8 Diphenyl-<3-hydroxy-1-phenyl-propyl>-phosphinoxid 
• 51713-17-8 4-(3-diphenylphosphinoyl-3-phenyl-propyl)-morpholine 
• 104601-13-0 Diphenyl-<3-hydroxy-1,2-diphenyl-propyl>-phosphinoxid 
• 32547-13-0 Diphenyl-<3-hydroxy-1,2,3-triphenyl-propyl>-phosphinoxid 

Relevant academic research and scientific papers

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds

The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium

Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.

Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source

Palladium-catalyzed C(sp3)–P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp3)–P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent.

Synthesis of benzyl sulfidesviasubstitution reaction at the sulfur of phosphinic acid thioesters

An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon-sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents. The developed method for benzyl sulfides has a wide substrate scope and was applicable for the synthesis of a drug analog.

Palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds

A palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds has been developed. Various benzylphosphorus compounds were produced in good to excellent yields with high functional group tolerance. All the three kinds of hydrogen phosphoryl compounds, i.e. H-phosphonates, H-phosphinates and secondary phosphine oxides, were applicable to this reaction. The successful scale-up experiment and one-pot synthetic operation also well demonstrated its practicality.

Copper-catalyzed C–P cross-coupling of arylmethyl quaternary ammonium salts via C–N bond cleavage

Abstract: A ligand-free copper-catalyzed C–P cross-coupling reaction of arylmethyl quaternary ammonium salts and diarylphosphine oxides in air is developed. Arylmethyl quaternary ammonium salts with various functional groups and a variety of dialkyl- and diarylphosphine oxides afford C–P cross-coupling products with good yields. This protocol requires no inert atmosphere, no ligand, and simple operation steps. Graphic abstract: [Figure not available: see fulltext.].

Preparation method of arylalkyl phosphorus oxide compounds

A preparation method of arylalkyl phosphorus oxide compounds is provided. The invention discloses a preparation method of several arylalkyl phosphorus oxide compounds. The preparation method includes:taking diphenylphosphine oxyhydrogen of 1.3 equivalent, 2.5% by mass nickel catalyst (with or without ligands) or palladium catalyst with ligands and a base of 1.5 equivalent from a glovebox, addingthem sequentially into a Schlenk reaction tube, adding a nitrile compound of 1.0 equivalent, vacuumizing, and backfilling with nitrogen; in the nitrogen atmosphere, adding a solvent, and allowing reaction to occur continuously at 120 DEG C for 16 h; after reaction, cooling to room temperature, and performing column chromatography separation to obtain the target product under high selectivity and high yield. The preparation method herein allows sp3C-CN\P-H cross coupling; reaction conditions are mild; operating is easy; the preparation process is simple; the target product has high conversion rate and high yield; the problems of other synthetic methods are solved that, for instance, two-step reaction system is complex, many organic and inorganic byproducts are produced, environmental pollution is caused easily, and the substrate range is narrow; the preparation method has a good industrial application prospect.

Method for preparing arylphosphine oxide derivatives

The invention discloses a method for preparing aryl phosphine oxide derivatives. According to the invention, potassium (hetero) arylmethyl trifluoroborate is used as a starting material, the raw material is easy to obtain and various in types, the material is solid, and storage and use are convenient; the products obtained by the method have various types and wide applications; the derivatives canbe conveniently converted into acylphosphine acylates, and the compounds can be widely used in the production of polymer materials, coatings, adhesives, adhesive tapes and the like as photoinitiators. In addition, the method has mild reaction conditions, high yield of the target product, little pollution, simple reaction operation and post-treatment process, and is suitable for industrial production.

Preparation method of aryl methyl phosphine acylate

The invention discloses a preparation method of aryl methyl phosphine acylate. The method uses (hetero) aryl acetic acid as the starting material, and the raw materials are easily available and have agreat variety. The product obtained by the method provided by the invention has various types and wide uses. The aryl methyl phosphine acylate can be easily converted into a bis (hetero)arylethene derivative, and the compound can be used for preparation of dyes, fluorescent agents, whiteners, light-emitting diodes and other devices. In addition, the method disclosed by the invention has the advantages of easily available, stable and low toxicity raw materials, mild reaction conditions, high yield of target product, low pollution, simple reaction operation and post-treatment process, and is suitable for industrial production.