2409-61-2

Usage

Uses

1. Organic Chemical Synthesis:
Bis(p-tolyl)phosphine oxide is used as an organic chemical synthesis intermediate for the production of a wide range of organic compounds. Its unique chemical properties make it a valuable building block in the creation of complex molecules.
2. Suzuki Reaction:
In the field of organic chemistry, Bis(p-tolyl)phosphine oxide is used as a catalyst in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds. The Suzuki reaction is particularly useful in the synthesis of biaryl compounds, which are prevalent in pharmaceuticals, agrochemicals, and advanced materials.
3. Chemical Industry:
Bis(p-tolyl)phosphine oxide is used in the chemical industry as a catalyst or reagent for various chemical reactions. Its ability to facilitate bond formation and its stability make it a preferred choice for numerous industrial applications.
4. Pharmaceutical Industry:
In the pharmaceutical industry, Bis(p-tolyl)phosphine oxide is utilized as a key intermediate in the synthesis of various drug molecules. Its role in creating complex structures is crucial for the development of new and effective medications.
5. Material Science:
Bis(p-tolyl)phosphine oxide is also used in the field of material science, where it contributes to the development of advanced materials with specific properties. Its involvement in the synthesis of these materials can lead to improved performance and novel applications.

InChI:InChI=1/C14H15OP/c1-11-3-7-13(8-4-11)16(15)14-9-5-12(2)6-10-14/h3-10,16H,1-2H3

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 1019-71-2 chlorodi-p-tolylphosphane 
• 762-04-9 Diethyl phosphonate 
• 13685-92-2 (diethylamino)[bis(4-methylphenyl)]phosphine 
• 106-38-7 para-bromotoluene 
• 106-43-4 para-chlorotoluene 
• 1017-60-3 di-p-tolylphosphine 

Downstream Products

• 106649-34-7 (Di-p-tolyl-phosphinoyl)-methanol 
• 145290-28-4 N,N-Dibutyl-2-(di-p-tolyl-phosphinoyl)-acetamide 
• 479578-14-8 {(R)-[2-(di-p-tolylphosphinoyl)naphthalen-1-yl](phenyl)methyl}methyl((1R')-1'-phenylethyl)amine 
• 479578-16-0 N-{(R)-[2-(di-p-tolylphosphinoyl)naphthalen-1-yl](phenyl)methyl}-N-((1'R)-1'-phenylethyl)acetamide 
• 1019-71-2 chlorodi-p-tolylphosphane 
• 1099827-85-6 2-(di-p-tolylphosphoryl)pyrrolidine 
• 1382465-13-5 (2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)di(p-tolyl)phosphine oxide 
• 159180-44-6 1,2-bis(di-p-tolylphosphinoyl)benzene 
• 1446248-67-4 C₂₄H₃₅OP 
• 18957-70-5 (phenyl)di(4-methylphenyl)phosphine oxide 
• 6840-28-4 diphenyl(p-tolyl)phosphine oxide 
• 52944-82-8 di-p-tolyl(vinyl)phosphine oxide 

Relevant academic research and scientific papers

Electrochemical Oxidative C–H Phosphonylation of thiazole derivatives in ambient conditions

We herein report a direct electrochemical dehydrogenative C–H phosphonylation of thiazoles derivatives with H2 evolution. Employing electricity as the green and sole oxidant, cheap metal as electrode, the anodic oxidation together with cathodic hydrogen evolution process provides a green and efficient strategy for C–H phosphonylation. A diverse range of phosphorus products were constructed under external metal and oxidant-free conditions at ambient temperature, featuring atom economy, simple operation and wide reaction scope.

Microwave-Assisted Ruthenium- and Rhodium-Catalyzed Couplings of α-Amino Acid Ester-Derived Phosphinamides with Alkynes

Two different types of new phosphinamide α-amino ester derivatives have been prepared in moderate to high yields via ruthenium(II) and rhodium(III)-catalyzed ortho-C?H functionalization under microwave irradiation. Specifically, the ortho-alkenylated phosphinamides were produced through coupling of phosphinamides containing an α-substituted or α,α-disubstituted α-amino ester with internal alkynes under ruthenium catalysis. In contrast, Ru and the more effective Rh-catalyzed coupling of the α-unsubstituted glycine ester phosphinamide with alkynes resulted in formation of oxidative annulation products, phosphaisoquinolin-1-ones. The developed methods feature the use of easily accessible starting materials, short reaction time, exclusive E-stereoselectivity (for ortho-alkenylation) and good functional group tolerance. The alkenylation reaction was readily scaled up to gram scale. Furthermore, the obtained alkenylated phosphinamide could be transformed into P-containing dipeptides through hydrolysis of the ester group in the catalysis product and subsequent condensation with an α-amino ester.

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction

A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.

Highly Enantioselective Synthesis of Phosphorus-Containing ?-Benzosultams by Bifunctional Phosphonium Salt-Promoted Hydrophosphonylation

?-Benzosultam derivatives are potential drug candidates with diverse biological activities. A series of chiral ?-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished. Some control experiments were also conducted to elucidate the plausible reaction mechanism of this chemical transformation.

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones

A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.

Twofold C?H Activation-Based Enantio- and Diastereoselective C?H Arylation Using Diarylacetylenes as Rare Arylating Reagents

C?H bond activation has been established as an attractive strategy to access axially chiral biaryls, and the most straightforward method is direct C?H arylation of arenes. However, the arylating source has been limited to several classes of reactive and bulky reagents. Reported herein is rhodium-catalyzed 1:2 coupling of diarylphosphinic amides and diarylacetylenes for enantio- and diastereoselective construction of biaryls with both central and axial chirality. This twofold C?H activation reaction stays contrast to the previously explored Miura–Satoh type 1:2 coupling of arenes and alkynes in terms of chemoselectivity and proceeded under mild conditions with the alkyne acting as a rare arylating reagent. Both C?H activation events are stereo-determining and are under catalyst control, with the 2nd C?H activation being diastereo-determining in a remote fashion. Analysis of the stereochemistry of the major and side products suggests moderate enantioselectivity of the initial C?H activation–desymmetrization process. However, the minor (R) rhodium vinyl intermediate is consumed more readily in undesired protonolysis, eventually resulting in high enantio- and diastereoselectivity of the major product.

Structure-based design, synthesis, and evaluation of the biological activity of novel phosphoroorganic small molecule IAP antagonists

One of the strategies employed by novel anticancer therapies is to put the process of apoptosis back on track by blocking the interaction between inhibitor of apoptosis proteins (IAPs) and caspases. The activity of caspases is modulated by the caspases themselves in a caspase/procaspase proteolytic cascade and by their interaction with IAPs. Caspases can be released from the inhibitory influence of IAPs by proapoptotic proteins such as secondary mitochondrial activator of caspases (Smac) that share an IAP binding motif (IBM). The main purpose of the present study was the design and synthesis of phosphorus-based peptidyl antagonists of IAPs that mimic the endogenous Smac protein, which blocks the interaction between IAPs and caspases. Based on the structure of the IAP antagonist and recently reported thiadiazole derivatives, we designed and evaluated the biochemical properties of a series of phosphonic peptides bearing the N-Me-Ala-Val/Chg-Pro-OH motif (Chg: cyclohexylglycine). The ability of the obtained compounds to interact with the binding groove of the X-linked inhibitor of apoptosis protein baculovirus inhibitor of apoptosis protein repeat (XIAP BIR3) domain was examined by a fluorescence polarization assay, while their potential to induce autoubiquitination followed by proteasomal degradation of cellular IAP1 was examined using the MDA-MB-231 breast cancer cell line. The highest potency against BIR3 was observed among peptides containing C-terminal phosphonic phenylalanine analogs, which displayed nanomolar Ki values. Their antiproliferative potential as well as their proapoptotic action, manifested by an increase in caspase-3 activity, was examined using various cell lines.