6840-26-2

Usage

Uses

Used in Organometallic Chemistry:
Phosphine oxide, (2-methylphenyl)diphenyl-, is utilized as a ligand in organometallic chemistry for its ability to form stable complexes with metal ions. This enhances the reactivity and selectivity of metal catalysts, making it a valuable component in various chemical processes.
Used in Organic Synthesis:
As a catalyst, Phosphine oxide, (2-methylphenyl)diphenyl-, plays a crucial role in facilitating numerous organic synthesis reactions. Its unique structure allows it to effectively coordinate with reactants, thereby improving the efficiency and yield of the reactions.
Used in Medicinal Chemistry Research:
Phosphine oxide, (2-methylphenyl)diphenyl-, has been studied for its potential biological and pharmacological activities. Its presence in medicinal chemistry research indicates the possibility of developing new therapeutic agents or enhancing existing ones through its unique properties and interactions.
Used in Catalyst Design:
In the design of catalysts, Phosphine oxide, (2-methylphenyl)diphenyl-, is employed to create more efficient and selective catalysts for a range of chemical reactions. Its structural features contribute to the development of advanced catalysts that can address specific challenges in chemical synthesis and processing.
Used in Pharmaceutical Industry:
Phosphine oxide, (2-methylphenyl)diphenyl-, is of interest in the pharmaceutical industry due to its potential applications in drug discovery and development. Its unique properties may contribute to the creation of novel drugs or the improvement of existing pharmaceutical compounds, ultimately benefiting patient care and treatment outcomes.

Upstream product

• 19493-09-5 Methylenetriphenylphosphorane 
• 74-88-4 methyl iodide 
• 791-28-6 Triphenylphosphine oxide 
• 4559-70-0 Diphenylphosphine oxide 
• 10050-08-5 tri-o-tolylbismuth 
• 529-19-1 2-Methylbenzonitrile 
• 7658-80-2 2-methylbenzohydrazide 
• 95-46-5 2-methylphenyl bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 55743-31-2 (1-chlorovinyl)diphenylphosphine oxide 
• 42096-33-3 o-tolyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 366-39-2 2-methylphenyl sulfurofluoridate 
• 53271-49-1 2-methylthiobenzoic acid S-p-tolyl ester 
• 118-90-1 ortho-methylbenzoic acid 

Downstream Products

• 68718-85-4 (2-(bromomethyl)phenyl)diphenylphosphine oxide 
• 1384422-34-7 (2-diphenylphosphinoyl)phenylmethyl-diphenylphosphine-borane 
• 68718-89-8 (2-(hydroxymethyl)phenyl)diphenylphosphine oxide 
• 5931-53-3 Diphenyl-o-tolylphosphin 
• 79317-63-8 o-diphenylphosphonylbenzoic acid methyl ester 
• 224564-59-4 2-(diphenylphosphinoyl)-α-<(2S,3S)-2,3-diphenylaziridine-1-yl>toluene 
• 1707-03-5 diphenyl-phosphinic acid 
• 18593-18-5 (2-methylphenyl)phenylphosphinic acid 
• 2572-40-9 (o-carboxyphenyl)diphenylphosphine oxide 

Relevant academic research and scientific papers

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.

Palladium-catalyzed C–P bond activation of aroyl phosphine oxides without the adjacent “anchoring atom”

A novel palladium-catalyzed decarbonylation of aroyl phosphine oxides to prepare phosphine oxides from carboxylic acids is developed. Without the adjacent “anchoring atom”, the challenging C–P bond activation is achieved in high selectivity. The disclosure of this reaction provides a new example of C–P bond activation and helps to extend the understanding of the property of C–P bond.

Copper-Catalyzed C?P Cross-Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange

An efficient protocol for concurrent tandem halogen exchange/C?P cross-coupling of cycloalkenyl bromides and secondary phosphine oxides has been developed. The catalytic system is based on cheap and air-stable copper(I) iodide as the precatalyst, commercially available N,N’-dimethylethylenediamine as the ligand, and Cs2CO3 or K2CO3 as the base. The use of sodium iodide as an additive reduces the excessive use of organic bromides to near-stoichiometric by promoting the in situ transformation to the corresponding iodides. Diarylphosphine oxides undergo cycloalkenylation with 35–99 % yields and dicyclohexylphosphine oxide with 30–53 % yields. In the case of acyclic alkenyl bromides the cross-coupling products undergo conjugate addition of diphenylphosphine oxide and satisfying yields are observed only for internal olefins. In the case of aryl bromides satisfying yields (43–72 %) are observed only for sterically unhindered arenes or arenes possessing an ortho-directing group. Cycloalkenylphosphine oxides prepared in the cross-coupling reaction undergo base-catalyzed and base-promoted conjugate addition to give bis(phosphinoyl)cycloalkanes.

Cu/Picolinamides-Catalyzed Coupling of (Hetero)aryl Halides with Secondary Phosphine Oxides and Phosphite?

Some 4-hydroxy-picolinic acid derived amides were revealed as more efficient ligands for Cu-catalyzed coupling of (hetero)aryl halides with secondary phosphine oxides and phosphites. Only 3—5 mol% CuI and ligands were required to ensure coupling with a number of (hetero)aryl bromides and iodides to complete at 120 oC in 10—20 h.

EUROPIUM COMPLEX

To provide europium complexes having high photostability. A europium complex expressed with the following formula (A): {wherein, RA and RB are independently a cyclic alkyl group with 3 to 10 carbons, respectively, and RC is a cyclic alkyl group with 3 to 10 carbons or a phenyl group expressed with the following formula (B): (wherein, XA, XB, AC, XD and XE independently represent a hydrogen atom; a fluorine atom; an alkyl group with 1 to 3 carbon(s); an alkyloxy group with 1 to 3 carbon(s); an aryloxy group with 6 to 10 carbons; a fluoroalkyl group with 1 to 3 carbon(s); a fluoroalkyloxy group with 1 to 3 carbon(s); or a phenyl group that may be substituted with a fluorine atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a fluorophenyl group, a hydroxyl group or a cyano group, respectively); RA is a cyclic alkyl group with 3 to 10 carbons; RB and RC are a phenyl group expressed with the formula (B), provided, however, that a case where RA a cyclohexyl group, and, RB and RC are a phenyl group is excluded; or RA, RB and RC independently represent an ortho-substituted phenyl group expressed with the following formula (Ba): (wherein, XE represents a hydrogen atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a naphthyl group that may be substituted with a fluorine atom, a pyridyl group that may be substituted with a fluorine atom, or a phenyl group that is expressed with a formula (C): [wherein, ZA, ZC and ZE independently represent a hydrogen atom, a fluorine atom, an alkyl group with 1 to 3 carbon(s), an alkyloxy group with 1 to 3 carbon(s), a fluoroalkyl group with 1 to 3 carbon(s), a fluoroalkyloxy group with 1 to 3 carbon(s), a phenyl group that may be substituted with a fluorine atom, a hydroxyl group or a cyano group; ZB and ZD independently represent a hydrogen atom or a fluorine atom, respectively], provided, however, that a case where RA, RB and RC are all a phenyl group is excluded), respectively; RD represents a hydrogen atom, a deuterium atom or a fluorine atom; WA and WB independently represent an alkyl group with 1 to 6 carbon(s), a fluoroalkyl group with 1 to 6 carbon(s), a phenyl group, a 2-thienyl group or a 3-thienyl group; and ‘n’ represents an integer of 1 to 3}.

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 Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)–H Compounds

A direct decarbonylative phosphorylation of benzoic acids catalyzed by palladium was disclosed. Under the reaction conditions, a wide range of benzoic acids coupled readily with all the three kinds of P(O)–H compounds, i.e. secondary phosphine oxides, H-phosphinates and H-phosphonates, producing the corresponding organophosphorus compounds in good to high yields. This reaction could be conducted at a gram scale and applied in the late-stage phosphorylative modification of carboxylic acids drug molecules. These results well demonstrated the potential synthetic value of this new reaction in organic synthesis.

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.

NOVEL CERIUM COMPLEX, AND LIGHT EMITTING MATERIAL

PROBLEM TO BE SOLVED: To provide a novel cerium carbene complex suitable for LED phosphors, organic EL emission layer materials, wavelength conversion materials for solar cells, and wavelength conversion materials for agriculture facility, and a method of producing the same. SOLUTION: The present invention provides a cerium complex with trivalent cerium coordinated with a carbene compound; particularly, a cerium complex in which the carbene compound coordinated to trivalent cerium being represented by formula (1). (R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 each represent a hydrogen atom, or a C1-20 hydrocarbon group, or a hydrocarbon group containing an oxygen atom or a phosphorus atom, where they may be bound to each other, to form a ring. R11, R12 each represent a hydrogen atom or a C1-20 hydrocarbon group, where they may be bound to each other, to form a ring. x is an integer of 0 to 10). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT