57311-18-9

Usage

Uses

Used in Organic Synthesis:
4-CHLORO-2-PHENYLPYRIDINE is used as an organic intermediate for the synthesis of various compounds. Its unique structure allows it to be a valuable building block in the creation of complex organic molecules, which can be utilized in a wide range of applications, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Manufacturing of Organic Light Emitting Diodes (OLEDs):
One of the most notable applications of 4-CHLORO-2-PHENYLPYRIDINE is in the manufacturing of organic light emitting diodes (OLEDs). OLEDs are a type of light-emitting technology that is widely used in display and lighting applications due to their high efficiency, thin and flexible form factor, and ability to produce vibrant colors. 4-CHLORO-2-PHENYLPYRIDINE plays a crucial role in the development of OLED materials, contributing to the advancement of this technology.

InChI:InChI=1/C11H8ClN/c12-10-6-7-13-11(8-10)9-4-2-1-3-5-9/h1-8H

Upstream product

• 1131-33-5 2-phenylpyridin N-oxide 
• 1121-76-2 4-chloropyridine N-oxide 
• 100-59-4 phenylmagnesium chloride 
• 26452-80-2 2,4-dichloropyridine 
• 98-80-6 phenylboronic acid 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 603-33-8 triphenylbismuthane 
• 22918-01-0 2-bromo-4-chloropyridine 
• 5470-22-4 4-chloropicolinic acid 
• 71-43-2 benzene 
• 626-61-9 4-Chloropyridine 
• 22918-03-2 2-iodo-4-pyridyl chloride 
• 21203-86-1 2-phenyl-pyridin-4-ylamine 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Downstream Products

• 417721-23-4 4-(2-Phenylpyridin-4-yl)oxyaniline 
• 417724-78-8 4-(4-nitrophenoxy)-2-phenylpyridine 
• 1265869-41-7 2-(2'-phenylpyridin-4'-ylsulfanyl)ethanamine 
• 1312471-21-8 2-phenyl-4-isopropylpyridine 
• 1414972-01-2 2-phenyl-4-(prop-1-en-2-yl)pyridine 
• 1215692-63-9 C₄₀H₃₀IrN₃ 
• 879291-26-6 2-(2-phenylpyridin-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1008-89-5 2-phenylpyridine 
• 37941-27-8 N,N-dimethyl-2-phenylpyridin-4-amine 
• 131814-36-3 4-(2-phenylpyridin-4-yl)morpholine 
• 1026055-99-1 4-chloro-2-phenylpyridine 1-oxide 

Relevant academic research and scientific papers

Deaminative chlorination of aminoheterocycles

Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]

Discovery of 9,10-dihydrophenanthrene derivatives as SARS-CoV-2 3CLpro inhibitors for treating COVID-19

The epidemic coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has now spread worldwide and efficacious therapeutics are urgently needed. 3-Chymotrypsin-like cysteine protease (3CLpro) is an indispensable protein in viral replication and represents an attractive drug target for fighting COVID-19. Herein, we report the discovery of 9,10-dihydrophenanthrene derivatives as non-peptidomimetic and non-covalent inhibitors of the SARS-CoV-2 3CLpro. The structure-activity relationships of 9,10-dihydrophenanthrenes as SARS-CoV-2 3CLpro inhibitors have carefully been investigated and discussed in this study. Among all tested 9,10-dihydrophenanthrene derivatives, C1 and C2 display the most potent SARS-CoV-2 3CLpro inhibition activity, with IC50 values of 1.55 ± 0.21 μM and 1.81 ± 0.17 μM, respectively. Further enzyme kinetics assays show that these two compounds dose-dependently inhibit SARS-CoV-2 3CLpro via a mixed-inhibition manner. Molecular docking simulations reveal the binding modes of C1 in the dimer interface and substrate-binding pocket of the target. In addition, C1 shows outstanding metabolic stability in the gastrointestinal tract, human plasma, and human liver microsome, suggesting that this agent has the potential to be developed as an orally administrated SARS-CoV-2 3CLpro inhibitor.

Selective Halogenation of Pyridines Using Designed Phosphine Reagents

Halopyridines are key building blocks for synthesizing pharmaceuticals, agrochemicals, and ligands for metal complexes, but strategies to selectively halogenate pyridine C-H precursors are lacking. We designed a set of heterocyclic phosphines that are installed at the 4-position of pyridines as phosphonium salts and then displaced with halide nucleophiles. A broad range of unactivated pyridines can be halogenated, and the method is viable for late-stage halogenation of complex pharmaceuticals. Computational studies indicate that C-halogen bond formation occurs via an SNAr pathway, and phosphine elimination is the rate-determining step. Steric interactions during C-P bond cleavage account for differences in reactivity between 2- and 3-substituted pyridines.

Palladium-catalyzed c-4 selective coupling of 2,4-dichloropyridines and synthesis of pyridine-based dyes for live-cell imaging

An alternative process of Pd-catalyzed C-4 selective coupling of 2,4-dichloropyridines with boronic esters was developed, which afforded 24 examples of C-4 coupled pyridines in moderate to good yields. After further arylation, 21 examples of C-2, C-4 diarylated pyridines with a significant photophysical property were obtained, which were applied as pyridine-based dyes into live-cell imaging with good biocompatibility and low toxicity.

Small organic molecules with tailored structures: Initiators in the transition-metal-free C-H arylation of unactivated arenes

Simple, small organic molecules containing nitrogen and oxygen atoms in their structures have been disclosed to catalyze transition-metal-free C-H arylation of unactivated arenes with aryl iodides in the presence of tBuOK. In this article, an optimized catalytically active molecule, (2-(methylamino)phenyl)methanol, was designed. A broad range of aryl iodides could be converted into the corresponding arylated products at 100 °C over 24 h with good to excellent yields. Mechanistic experiments verified that radicals participated in this catalytic transformation and that the cleavage of the aromatic C-H bond was not the rate determining step. A K+ capture experiment by 18-crown-6 emphasized the significance of the cation species of the strong base. Fourier transform infrared spectroscopy proved that the catalytic system was activated by the hydrogen bonds between small organic molecules and tBuOK. Also, a clear mechanism was proposed. This transition-metal-free method affords a promising system for efficient and inexpensive synthesis of biaryls via a user-friendly approach, as confirmed by scale-up experiments.

Red to blue emitting cationic iridium complexes with 2-phenyl-4-dimethylaminopyridine as the cyclometalating ligand: Synthesis, characterization and electroluminescent devices

2-Phenyl-4-dimethylaminopyridine (dmappy) with high 3π-π? triplet energy is, for the first time, employed as the cyclometalating ligand for constructing cationic iridium complexes with tunable emission properties. Three complexes, na

Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.

C6-Selective Direct Arylation of 2-Phenylpyridine via an Activated N-methylpyridinium Salt: A Combined Experimental and Theoretical Study

An elegant pre-activation strategy, based on the formation of N-methylpyridinium iodide salts for C6-selective direct arylation of 2-phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6-diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C?H bond acidity is improved significantly in N-methylpyridinium salts compared with their N-Oxide and N-iminopyridinium ylide counterparts, thus solving the long-standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd-catalyzed and Cu-mediated mechanism in which a carbenoid copper species that is formed in-situ from N-methylpyridinium salts, participates in a Pd-catalyzed arylation followed by an iodide-promoted N-demethylation process. (Figure presented.).

ORGANOMETALLIC COMPLEX, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC APPARATUS, AND LIGHTING DEVICE

PROBLEM TO BE SOLVED: To provide a novel organometallic complex that emits phosphorescence with high color purity. SOLUTION: An organometallic complex, represented by general formula (G1), comprises iridium and a plurality of ligands each having a 2-phenylpyridine skeleton. In the organometallic complex, one or two of the ligands have a carbazole skeleton at a 4-position of the 2-phenylpyridine skeleton. (R1 to R8 and R9 to R23 are an alkyl group, an aryl group or the like). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Non-transition metal-catalyzed 2-phenylpyridine compound synthesis method

The invention relates to a pharmaceutical and chemical intermediate preparation method, in particular to a non-transition metal-catalyzed 2-phenylpyridine compound synthesis method. A 2-phenylpyridine compound serves as an important component of a plurality of pharmacologically active molecules and bioactive molecules, has important application value in the fields of organic synthesis, pharmaceutical chemistry and the like, and is broad in market prospect. According to the non-transition metal-catalyzed 2-phenylpyridine compound synthesis method, namely a non-transition metal-catalyzed 2-phenylpyridine derivative synthesis method, pyridine-2-formic acid and benzene are adopted as raw materials; and under the presence of one or more alkalis and free radical initiators, the 2-phenylpyridine compound is synthesized in the mild condition. The non-transition metal-catalyzed 2-phenylpyridine compound synthesis method provided by the invention has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction condition is mild, as well as the use value and the social and economic benefits are relatively great.