2959-74-2

Basic information

• Product Name: benzyl(diphenyl)phosphane oxide
• Synonyms: Benzyl(diphenyl)phosphine oxide
• CAS NO: 2959-74-2
• Molecular Formula: C₁₉H₁₇OP
• Molecular Weight: 292.3114
• Mol File: 2959-74-2.mol

Chemical Properties

• Boiling Point: 423°C at 760 mmHg
• Flash Point: 209.6°C
• Density: 1.15g/cm³
• Vapor Pressure: 5.67E-07mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: benzyl(diphenyl)phosphane oxide(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl(diphenyl)phosphane oxide(2959-74-2)
• EPA Substance Registry System: benzyl(diphenyl)phosphane oxide(2959-74-2)

Safety Data

• Hazardous Substances Data: 2959-74-2(Hazardous Substances Data)

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

• 64-17-5 ethanol 
• 78200-70-1 benzyl-dichloro-diphenyl-phosphorane 
• 1707-03-5 diphenyl-phosphinic acid 
• 108-97-4 4-pyrone 
• 17507-57-2 (diphenylphosphinyl)phenyldiazomethane 
• 98-87-3 benzylidene dichloride 
• 64436-23-3 bis-(α-diphenylphosphinoyl-benzyl)-ether 
• 119-61-9 benzophenone 
• 33417-25-3 Benzylbenzylidendiphenylphosphoran 
• 118214-15-6 Lithium(I)- 
• 111-71-7 heptanal 
• 7751-69-1 α-chlorobenzyl(diphenyl)phosphine oxide 
• 70052-65-2 [(2-bromophenyl)methyl]diphenylphosphine oxide 
• 78926-15-5 (α-bromobenzyl)diphenylphosphine oxide 

Downstream Products

• 5097-93-8 trans-4-styrylpyride 
• 2633-06-9 (E)-3-(2-phenylvinyl)pyridine 
• 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 
• 1608-41-9 1,4-distyrylbenzene 
• 101896-50-8 (2-hydroxy-1,2-diphenylethyl)diphenylphosphine oxide 
• 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 articles and documents

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.

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.

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.

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.].

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.

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.

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.

Preparation method of alkyl phosphorylated substances

The invention discloses a preparation method of alkyl phosphorylated substances. According to the invention, alkyl carboxylic acid is used as a starting material, and raw materials are easy to obtain and are various in types. Products prepared by the method disclosed by the invention are various in types and wide in application; and a part of the products can be prepared into important phosphorus ligands and drug key intermediates through simple reduction. In addition, use of high-toxicity phosphine reagents is avoided in the method, the reaction conditions are mild, operation is simple, the yield of the target product is high, pollution is small, and the reaction operation and post-treatment processes are simple, so that the method is suitable for industrial production.

Ni-Catalyzed C-P Coupling of Aryl, Benzyl, or Allyl Ammonium Salts with P(O)H Compounds

A methodology that allows for the construction of C-P bonds via the nickel-catalyzed cross-coupling of organoammonium salts with appropriate phosphorus nucleophiles has been developed. Aryl-, pyridyl-, benzyl-, and allyl-ammonium triflates can be employed as the electrophiles. The employed phosphorus-based nucleophiles included diaryl/dibutyl phosphine oxide, dialkyl phosphonates, and ethyl phenylphosphinate. Functional groups OMe, CN, CF3, F, Cl, C(O)NMe2, and C(O)tBu were tolerated.