89076-64-2

Basic information

• Product Name: 5-NITRO-2-PHENYLPYRIDINE
• Synonyms: 5-NITRO-2-PHENYLPYRIDINE;5-NITRO-2-METHYLANISOLE;(5-Nitropyridin-2-yl)benzene;3-Nitro-6-phenylpridine
• CAS NO: 89076-64-2
• Molecular Formula: C₁₁H₈N₂O₂
• Molecular Weight: 200.19
• Mol File: 89076-64-2.mol

Chemical Properties

• Melting Point: 116-118°
• Boiling Point: 344.1 °C at 760 mmHg
• Flash Point: 161.9 °C
• Appearance: /
• Density: 1.252 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-NITRO-2-PHENYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITRO-2-PHENYLPYRIDINE(89076-64-2)
• EPA Substance Registry System: 5-NITRO-2-PHENYLPYRIDINE(89076-64-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 89076-64-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Nitro-2-phenylpyridine is utilized as a key building block in the preparation of a variety of pharmaceuticals, agrochemicals, and other functional materials. Its unique structure and reactivity make it a valuable component in the development of new molecules with desired properties.
Used as a Reagent in Chemical Reactions:
In the realm of chemical reactions, 5-Nitro-2-phenylpyridine is employed as a reagent to introduce the 5-nitro-2-phenylpyridine moiety into target molecules. This allows for the creation of new compounds with specific functionalities, contributing to the advancement of organic chemistry and the discovery of novel substances with potential applications in various industries.
Used in Pharmaceutical Industry:
5-Nitro-2-phenylpyridine is used as an intermediate in the synthesis of pharmaceuticals, where its incorporation can lead to the development of new drugs with improved therapeutic effects. Its presence in the molecular structure can influence the pharmacokinetics and pharmacodynamics of the resulting compounds, potentially enhancing their efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Nitro-2-phenylpyridine is used as a precursor in the synthesis of various agrochemicals, including pesticides and herbicides. Its ability to be modified through chemical reactions allows for the creation of compounds with targeted effects on pests or weeds, contributing to more effective and environmentally friendly agricultural practices.
Overall, 5-Nitro-2-phenylpyridine's diverse applications across different industries highlight its importance as a synthetic intermediate and reagent, driving innovation and development in the fields of pharmaceuticals, agrochemicals, and beyond.

Upstream product

• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 98-86-2 acetophenone 
• 7196-01-2 4-(1-phenylvinyl)morpholine 
• 4548-45-2 2-chloro-5-nitropyridine 
• 98-80-6 phenylboronic acid 
• 4487-59-6 2-bromo-5-nitropyridine 
• 108-86-1 bromobenzene 
• 3433-56-5 1-(1-phenylvinyl)pyrrolidine 
• 4747-13-1 α-methoxystyrene 
• 30651-24-2 5-nitropicolinic acid 
• 71-43-2 benzene 
• 100-58-3 phenylmagnesium bromide 
• 603-33-8 triphenylbismuthane 
• 5418-51-9 5-nitro-2-hydroxypyridine 

Downstream Products

• 126370-67-0 6-phenylpyridin-3-amine 
• 1332586-73-8 N-(6-phenylpyridin-3-yl)-4-sulfamoylbenzamide 
• 1332586-74-9 4-cyano-N-(6-phenylpyridin-3-yl)benzamide 
• 1357166-19-8 2-(5-nitropyridine-2-yl)phenol 
• 1357165-44-6 C₁₁H₈N₃⁽¹⁺⁾*Cl^(1-) 
• 1357164-10-3 4-amino-3-(6-phenylpyridine-3-ylazo)naphthalene-1-sulfonic acid sodium salt 
• 1344663-50-8 2-phenyl-5-nitropyridine N-oxide 
• 1344663-92-8 2-cyclohexyl-3-nitro-6-phenylpyridine-1-oxide 
• 1344663-91-7 3-nitro-2-isopropyl-6-phenylpyridine-1-oxide 
• 1344663-90-6 3-nitro-6-phenyl-2-p-tolylpyridine-1-oxide 
• 1335110-50-3 5-nitro-2,4-diphenylpyridine 
• 849353-27-1 (6-phenylpyridin-3-yl)carbamic acid ter-butyl ester 

Relevant articles and documents

Selective Chemical Functionalization at N6-Methyladenosine Residues in DNA Enabled by Visible-Light-Mediated Photoredox Catalysis

Selective chemistry that modifies the structure of DNA and RNA is essential to understanding the role of epigenetic modifications. We report a visible-light-activated photocatalytic process that introduces a covalent modification at a C(sp3)-H bond in the methyl group of N6-methyl deoxyadenosine and N6-methyl adenosine, epigenetic modifications of emerging importance. A carefully orchestrated reaction combines reduction of a nitropyridine to form a nitrosopyridine spin-trapping reagent and an exquisitely selective tertiary amine-mediated hydrogen-atom abstraction at the N6-methyl group to form an α-amino radical. Cross-coupling of the putative α-amino radical with nitrosopyridine leads to a stable conjugate, installing a label at N6-methyl-adenosine. We show that N6-methyl deoxyadenosine-containing oligonucleotides can be enriched from complex mixtures, paving the way for applications to identify this modification in genomic DNA and RNA.

Suzuki-Miyaura Cross-Couplings under Acidic Conditions

Suzuki-Miyaura reactions with Pd(PPh 3) 4 have been carried out using lithium N -phenylsydnone-4-carboxylate as additive, which gave best yields at pH 5.7 in a mixture of acetic acid, water, and sodium carbonate. Reaction parameters such as the Pd source, the solvent, reaction time and temperature, acid, base and carboxylate have been varied and some representative examples of the Suzuki-Miyaura reaction have been examined.

METHODS OF USING INDAZOLE-3-CARBOXAMIDES AND THEIR USE AS WNT/B-CATENIN SIGNALING PATHWAY INHIBITORS

This disclosure features the use of one or more indazole-3-carboxamide compounds or salts or analogs thereof, in the treatment of one or more diseases or conditions independently selected from the group consisting of a tendinopathy, dermatitis, psoriasis, morphea, ichthyosis, Raynaud's syndrome, and Darier's disease; and/or for promoting wound healing. The methods include administering to a subject (e.g., a subject in need thereof) a therapeutically effective amount of one or more indazole-3-carboxamide compounds or salts or analogs thereof as described anywhere herein.

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.

Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine

The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine (3) are reported. The electron-deficient nature of 3 permits rapid cycloaddition with a variety of electron-rich dienophiles, including amidines, enamines, enol ethers, ynamines, and ketene acetals in high to moderate yields. 1H NMR studies of a representative cycloaddition reaction between 3 and an amidine revealed a remarkable reaction rate and efficiency (1 mM, 3CN, 23 °C, >95%).

A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents

The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.

Newly-generated Al(OH)3-supported Pd nanoparticles-catalyzed Stille and Kumada coupling reactions of diazonium salts, (Het)aryl chlorides

A ligand-free Pd/Al(OH)3 nano-catalyst which is prepared by one-pot three-component method using Pd(PPh3)4, tetra (ethylene glycol), and aluminum tri-sec-butoxide exhibits excellent catalytic activity in Stille cross-couplings of (Het)aryl chlorides, arenediazonium tetrafluoroborate salts with phenyltributylstannane, respectively, and Kumada couplings of (Het)aryl chlorides with various Grignard reagents. More importantly, these two processes show excellent functional group compatibility with moderate to good yields and they are also versatile with respect to not only (Het)aryl chlorides, but also diazonium salts, and heteroaryl Grignard reagents. The nano-catalyst could also be recycled and reused 5 times without loss of activity and decrease of yield.

5-SUBSTITUTED INDAZOLE-3-CARBOXAMIDES AND PREPARATION AND USE THEREOF

Indazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of an indazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, Alzheimer's disease, lung disease, fibrotic disorders, cartilage (chondral) defects, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, and neurological conditions/disorders/diseases linked to overexpression of DYRK1A.

Complete Switch of Selectivity in the C-H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups

A complete switch in the CpIr(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the β-H elimination, which ultimately affords the observed chemoselectivity.

Organo functionalized graphene with Pd nanoparticles and its excellent catalytic activity for Suzuki coupling reaction

Synthesis of well distributed palladium nanoparticles (3-7 nm) on organo di-amine functionalized graphene is reported, which demonstrated excellent catalytic activity for Suzuki coupling reaction. Organo functionalized graphene support acted as an excellent host which helped in avoiding "Ostwald ripening" i.e., preventing palladium nanoparticle sintering and because of which the catalyst as a whole showed excellent catalytic activity for Suzuki coupling reaction. The catalytic material was characterized by X-ray diffraction (XRD), Fourier-transfer infrared spectroscopy (FTIR), Raman spectra, X-ray photoelectron spectra (XPS), and Scanning electron microscope (SEM), Transmittance electron microscopy (TEM) analysis. FT-IR revealed that the organic amine functional group was successfully grafted onto the graphene oxide surface. The formation of palladium nanoparticles was confirmed by XPS techniques. The catalytic activity in the coupling reaction using idobenzene was superb with 100% conversion and 98% yield and also activity remained almost unaltered up to six cycles. Typically, an extremely high turnover frequency of 185,078 h-1 or 3,084.64 min-1 is observed in the C-C Suzuki coupling reaction using organo di-amine functionalized graphene as catalyst. Experiments were also conducted under identical conditions to prove heterogeneity of the catalyst.