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Usage

Uses

Used in Plastics and Polymers Industry:
Phenyldi-p-tolylphosphine oxide is used as a stabilizer and flame retardant for plastics and polymers. Its phosphorus-based structure provides excellent fire retardant properties by releasing phosphorus radicals and reducing the formation of flammable gases during combustion.
Used in Organic Synthesis and Catalysis:
Phenyldi-p-tolylphosphine oxide is used as a reagent and catalyst in organic synthesis and catalysis due to its unique reactivity and coordination abilities with transition metals. This makes it a versatile chemical with diverse applications in industry and research.

Upstream product

• 25862-12-8 bis(4-methylphenyl) selenoxide 
• 791-28-6 Triphenylphosphine oxide 
• 1774-35-2 di(p-tolyl) sulfoxide 
• 2409-61-2 di(p-tolyl)phosphine oxide 
• 66003-76-7 Diphenyliodonium triflate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 17763-67-6 Phenyl triflate 
• 106-44-5 p-cresol 
• 660-34-4 p-methy lphenylfluorosulfate 
• 65-85-0 benzoic acid 
• 10371-42-3 S-(4-methylphenyl) thiobenzoate 
• 98-88-4 benzoyl chloride 
• 108-86-1 bromobenzene 

Downstream Products

• 19934-95-3 (phenyl)di(4-methylphenyl)phosphine 

Relevant academic research and scientific papers

Aryltrimethylammonium Tetrafluoroborates in Nickel-Catalyzed C–P Bond-Forming Reactions

Abstract: The first nickel-catalyzed phosphorylation of aryltrimethylammonium tetrafluoroborates with the formation of C–P bond instead of C–N has been developed. Starting from easily available and inexpensive aromatic amines, a variety of important arylphosphonates have been synthesized in moderate to excellent yields.

Microwave assisted P–C coupling reactions without directly added P-ligands

Our group introduced a green protocol for the Pd(OAc)2- or NiCl2-catalyzed P–C coupling reaction of aryl halides and various > P(O)H-compounds under MW conditions without directly added P-ligands. The reactivity of a few aryl derivatives in the Pd(OAc)2-catalyzed Hirao reaction was also studied. An induction period was observed in the reaction of bromobenzene and diphenylphosphine oxide. Finally, the less known copper(I)-promoted P–C coupling reactions were investigated experimentally. The mechanism was explored by quantum chemical calculations.

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-induced ligand to metal charge transfer excitation enabled phosphorylation of aryl halides

We herein described a visible light induced nickel(II)-catalyzed cross-coupling of secondary phosphine oxides with aryl halides. The Ni(I)species and chlorine atom radical Cl˙ were generatedviathe ligand to metal charge transfer (LMCT) process of the NiCl2(PPh3)2, which allows nickel(IV)-phosphorus speciesin situformation, giving various tertiary phosphine oxides under photocatalyst-free conditions.

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.

Experimental and theoretical study on the "2,2′-bipiridyl-Ni-catalyzed"hirao reaction of > P(O)H reagents and halobenzenes: A Ni(0) → Ni(II) or a Ni(II) → Ni(IV) mechanism?

It was found by us that the P.C coupling reaction of >P(O)H reagents with PhX (X = I and Br) in the presence of NiCl2/Zn as the precursors for the assumed Ni(0) complexant together with 2,2′-bipyridine as the ligand took place only with PhI at 50/70 °C. M06-2X/6-31G(d,p)//PCM(MeCN) calculations for the reaction of Ph2P(O)H and PhX revealed a favorable energetics only for the loss of iodide following the oxidative addition of PhI on the Ni(0) atom. However, the assumed transition states with Ni(II) formed after P-ligand uptake and deprotonation could not undergo reductive elimination meaning a "dead-end route". Hence, it was assumed that the initial complexation of the remaining Ni2+ ions with 2,2′-bipyridine may move the P-C coupling forward via a Ni(II) → Ni(IV) transition. This route was also confirmed by calculations, and this mechanism was justified by preparative experiments carried out using NiCl2/bipyridine in the absence of Zn. Hence, the generally accepted Ni(0) → Ni(II) route was refuted by us, confirming the generality of the Ni(II) → N(IV) protocol, either in the presence of bipyridine, or using the excess of the >P(O)H reagent as the P-ligand. The results of the calculations on the complex forming ability of Ni(0) and Ni(II) with 2,2′-bipyridine or the P-reagents were in accord with our mechanistic proposition.

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.

General Oxidative Aryl C-P Bond Formation through Palladium-Catalyzed Decarbonylative Coupling of Aroylhydrazides with P(O)H Compounds

Oxidative C-C/P-H cross-coupling is achieved via Pd-catalyzed decarbonylative cross-coupling of aroylhydrazides with P(O)H compounds. The unique cooperative reaction system, especially the Br?nsted acid and bidentate phosphine ligand, allows the selective activation of the inert C-C bond and the suppression of the undesired oxidation and coordination of >P(O)-H compounds, leading to a general oxidative synthesis of aryl phosphorus compounds from easily available substrates.

Photoinduced Transition-Metal-Free Cross-Coupling of Aryl Halides with H-Phosphonates

Photoinduced transition-metal- and photosensitizer-free cross-coupling of aryl halides (including Ar-Cl, Ar-Br, and Ar-I) with H-phosphonates (including dialkyl phosphonates and diarylphosphine oxides) is reported. Various functional groups were tolerated, including ester, methoxy, dimethoxy, alkyl, phenyl, trifluoromethyl, and heterocyclic compounds. This simple and green strategy provides a practical pathway to synthesize arylphosphine oxides.

Preparation of organophosphorus compounds from P-H compounds using o-(trimethylsilyl)aryl triflates as aryne precursors

An efficient method was developed for the synthesis of a variety of arylphosphorus compounds from P-H compounds using o-(trimethylsilyl)aryl triflates as aryne precursors. The reaction provides a practical preparation of various arylphosphorus compounds via aryne intermediates utilizing diarylphosphine oxides and dialkyl phosphites as the nucleophiles.