3582-84-1

Basic information

• Product Name: diphenyl(2-phenylethyl)phosphane oxide
• CAS NO: 3582-84-1
• Molecular Formula: C₂₀H₁₉OP
• Molecular Weight: 306.338
• Mol File: 3582-84-1.mol

Chemical Properties

• Boiling Point: 437.5°C at 760 mmHg
• Flash Point: 218.4°C
• Density: 1.14g/cm³
• Vapor Pressure: 1.91E-07mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: diphenyl(2-phenylethyl)phosphane oxide(CAS DataBase Reference)
• NIST Chemistry Reference: diphenyl(2-phenylethyl)phosphane oxide(3582-84-1)
• EPA Substance Registry System: diphenyl(2-phenylethyl)phosphane oxide(3582-84-1)

Safety Data

• Hazardous Substances Data: 3582-84-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Diphenyl(2-phenylethyl)phosphane oxide is utilized as a chiral auxiliary, which is instrumental in the production of chiral alcohols and amines. Its ability to influence the stereochemistry of reactions makes it a valuable tool in creating enantiomerically pure compounds.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, diphenyl(2-phenylethyl)phosphane oxide is employed to facilitate the creation of chiral molecules with a specific three-dimensional arrangement. This is crucial for the development of pharmaceuticals, agrochemicals, and fine chemicals, where the stereochemistry of a molecule can significantly affect its biological activity.
Used in Pharmaceutical Production:
Diphenyl(2-phenylethyl)phosphane oxide plays a role in the synthesis of pharmaceuticals, contributing to the development of new drugs with improved efficacy and selectivity. Its use in asymmetric synthesis ensures that the desired enantiomer of a drug molecule is produced, which is essential for the drug's therapeutic effects and safety.
Used in Agrochemical Production:
Similarly, in agrochemicals, diphenyl(2-phenylethyl)phosphane oxide aids in the synthesis of chiral pesticides and other crop protection agents. The ability to produce specific enantiomers can lead to more effective and environmentally friendly products.
Used in Fine Chemicals Production:
Diphenyl(2-phenylethyl)phosphane oxide is also used in the production of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, flavors, and specialty chemicals. Its role in asymmetric synthesis ensures the creation of high-quality enantiomerically pure products.

Upstream product

• 591-51-5 phenyllithium 
• 43017-31-8 1-phenyl-octahydro-1-phospha-2,3-cyclo-dicyclopropa[a,cd]pentalene 1-oxide 
• 5952-49-8 (2-phenylethyl)diphenylphosphane 
• 103-82-2 phenylacetic acid 
• 1079-66-9 chloro-diphenylphosphine 
• 100-42-5 styrene 
• 4559-70-0 Diphenylphosphine oxide 
• 795-47-1 (E)-diphenyl(styryl)phosphine oxide 
• 123-62-6 propionic acid anhydride 
• 536-74-3 phenylacetylene 
• 829-85-6 diphenylphosphane 
• 96-09-3 styrene oxide 
• 13887-07-5 anti-9-phenyl-9-phosphabicyclo<4.2.1>nona-2,4,7-trien 
• 43017-15-8 9-phenyl-9-phosphabicyclo[4.2.1]nonatriene oxide 

Downstream Products

• 73270-38-9 1,3-diphenyl-2-(diphenylphosphinoyl)propan-1-one 
• 172420-63-2 (E)-3-diphenylphosphinoyl-4-phenyl-butane-2-one 
• 5952-49-8 (2-phenylethyl)diphenylphosphane 
• 50485-27-3 2-benzyl-1,3-diphenyl-1-propene 
• 75593-28-1 (3-methylpent-2-en-1-yl)benzene 
• 62491-62-7 (E)-(3-methylpent-2-en-1-yl)benzene 
• 3412-44-0 (1E)-1,3-diphenylpropene 
• 5209-18-7 cis-1,3-diphenylpropene 
• 115693-91-9 (2R,3R)-2-(Diphenyl-phosphinoyl)-3-methyl-1-phenyl-pentan-3-ol 
• 115693-91-9 (2R,3S)-2-(Diphenyl-phosphinoyl)-3-methyl-1-phenyl-pentan-3-ol 

Relevant articles and documents

Hydrophosphinylation of Styrenes Catalysed by Well-Defined s-Block Bimetallics

Advancing the applications of s-block heterobimetallic complexes in catalysis, we report the use of potassium magnesiate (PMDETA)2K2Mg(CH2SiMe3)4 [PMDETA=N,N,N’,N’,N’’-pentamethyldiethylenetriamine] f

Nickel-catalyzed coupling of R2P(O)Me (R = aryl or alkoxy) with (hetero)arylmethyl alcohols

α-Alkylation of methyldiarylphosphine oxides with (hetero)arylmethyl alcohols was performed under nickel catalysis. Various arylmethyl and heteroarylmethyl alcohols can be used in this transformation. A series of methyldiarylphosphine oxides were alkylated with 30-90% yields. Functional groups on the aromatic rings of methyldiarylphosphine oxides or arylmethyl alcohols including OMe, NMe2, SMe, CF3, Cl, and F groups can be tolerated. The conditions are also suitable for the α-alkylation reaction of dialkyl methylphosphonates.

Potassium tert -Butoxide Mediated Reductive C-P Cross-Coupling of Arylvinyl Sulfides through C-S Bond Cleavage

A transition-metal-free t -BuOK-mediated reductive C-P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C-S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C-P bond through C-S bond cleavage and reduction of a C-C double bond in one pot.

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.

Lanthanum-Catalyzed Regioselective Anti-Markovnikov Hydrophosphinylation of Styrenes

A useful and convenient method for sp3 C-P(O) bond formation via direct regioselective hydrophosphinylation of simple and readily available alkenes using a lanthanum-based N,N-dimethylbenzylamine complex (La(DMBA)3) as a precatalyst is demonstrated. The reaction proceeds with perfect atom economy for a wide range of styrenes with secondary phosphine oxides, giving moderate to excellent yields.

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.

Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation

The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.

Direct C-OH/P(O)-H dehydration coupling forming phosphine oxides

A t-BuONa-mediated C-OH/P(O)-H cross dehydration coupling to produce alkylphosphine oxides is developed. This reaction employed readily available alcohols and P(O)-H compounds as the starting materials, providing an efficient alternative method for constructing sp3 C-P bonds. A reasonable reaction path involving dehydration and subsequent regio-selective hydrophosphorylation of the resulting alkenes was proposed.

T-BuOK-mediated reductive addition of P(O)-H compounds to terminal alkynes forming β-arylphosphine oxides

A novel and efficient t-BuOK-mediated reductive addition of P(O)-H compounds to terminal alkynes was developed. A variety of β-arylphosphine oxides including the valuable β-heteroarylphosphine oxides were produced in moderate to high yields under mild reaction conditions. This reaction may proceed via a tandem process involving regio-selective double addition and subsequent transfer hydrogenation.

Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones

A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.