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2-Phenylpyridine

Base Information
  • Chemical Name:2-Phenylpyridine
  • CAS No.:1008-89-5
  • Molecular Formula:C11H9N
  • Molecular Weight:155.199
  • Hs Code.:29333999
  • European Community (EC) Number:213-763-1,635-640-5
  • NSC Number:89291
  • UNII:2Y6S09838Q
  • DSSTox Substance ID:DTXSID6074417
  • Nikkaji Number:J45.968B
  • Wikipedia:2-Phenylpyridine
  • Wikidata:Q18205048
  • ChEMBL ID:CHEMBL1193163
  • Mol file:1008-89-5.mol
2-Phenylpyridine

Synonyms:2-phenylpyridine

Suppliers and Price of 2-Phenylpyridine
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • 2-Phenylpyridine
  • 2kg
  • $ 4125.00
  • TCI Chemical
  • 2-Phenylpyridine >98.0%(GC)
  • 25g
  • $ 96.00
  • TCI Chemical
  • 2-Phenylpyridine >98.0%(GC)
  • 5g
  • $ 30.00
  • SynQuest Laboratories
  • 2-Phenylpyridine 98%
  • 100 g
  • $ 141.00
  • Strem Chemicals
  • 2-Phenylpyridine, 95%
  • 1g
  • $ 21.00
  • Sigma-Aldrich
  • 2-Phenylpyridine 98%
  • 50g
  • $ 285.00
  • Sigma-Aldrich
  • 2-Phenylpyridine for synthesis. CAS 1008-89-5, molar mass 155.2 g/mol., for synthesis
  • 8400410025
  • $ 123.00
  • Sigma-Aldrich
  • 2-Phenylpyridine for synthesis
  • 25 mL
  • $ 117.47
  • Sigma-Aldrich
  • 2-Phenylpyridine 98%
  • 10g
  • $ 78.40
  • Oakwood
  • 2-Phenylpyridine 98%
  • 25g
  • $ 50.00
Total 143 raw suppliers
Chemical Property of 2-Phenylpyridine
Chemical Property:
  • Appearance/Colour:Light yellow liquid 
  • Vapor Pressure:0.0111mmHg at 25°C 
  • Melting Point:-5 °C 
  • Refractive Index:n20/D 1.623(lit.)  
  • Boiling Point:270.8 °C at 760 mmHg 
  • PKA:4.44±0.25(Predicted) 
  • Flash Point:113.3 °C 
  • PSA:12.89000 
  • Density:1.086 g/cm3 
  • LogP:2.74860 
  • Storage Temp.:Store below +30°C. 
  • Sensitive.:air sensitive 
  • Water Solubility.:Fully miscible with ethanol, acetone, toluene, methylene chloride. Not miscible in water. 
  • XLogP3:2.6
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:1
  • Exact Mass:155.073499291
  • Heavy Atom Count:12
  • Complexity:127
Purity/Quality:

99% *data from raw suppliers

2-Phenylpyridine *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/37/38 
  • Safety Statements: 26-37/39-36 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Pyridines
  • Canonical SMILES:C1=CC=C(C=C1)C2=CC=CC=N2
  • General Description 2-Phenylpyridine (also known as o-phenylpyridine or 2-phenyl pyridine) is a versatile aromatic compound commonly used as a ligand in coordination chemistry, particularly in cyclometalated iridium(III) complexes for applications in OLEDs, sensors, and biological tags. It serves as a key building block in catalytic systems, such as palladium(II) complexes for Mizoroki-Heck cross-coupling reactions, where its π-acceptor properties influence catalytic efficiency. Additionally, it has been explored as a substrate in enzymatic oxyfunctionalization studies, where engineered toluene dioxygenase variants can convert it into chiral diols. Its structural adaptability and electronic properties make it valuable in synthetic and materials chemistry.
Technology Process of 2-Phenylpyridine

There total 514 articles about 2-Phenylpyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With potassium phosphate; palladium diacetate; In water; at 100 ℃; for 4h; Inert atmosphere; Green chemistry;
DOI:10.1021/acs.oprd.6b00180
Guidance literature:
With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; In 1,2-dichloro-ethane; at 100 ℃; for 16h; Reagent/catalyst; regioselective reaction;
DOI:10.1021/acscatal.5b01753
Guidance literature:
With copper(l) iodide; cesium fluoride; In N,N-dimethyl-formamide; at 120 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ol402701x
Refernces

Semi-Rational Engineering of Toluene Dioxygenase from Pseudomonas putida F1 towards Oxyfunctionalization of Bicyclic Aromatics

10.1002/adsc.202100296

The research focuses on the semi-rational engineering of toluene dioxygenase (TDO) from Pseudomonas putida F1 to enhance its capability for the oxyfunctionalization of bicyclic aromatic compounds. The study involved generating single and double mutant libraries targeting 27 different positions at the active site and entrance channel of TDO. A total of 176 variants were created and tested with substrates such as naphthalene, 1,2,3,4-tetrahydroquinoline, and 2-phenylpyridine. Key mutations at positions M220, A223, and F366 significantly influenced product formation, chemo-, regio-, and enantioselectivity. The engineered TDO variants demonstrated the ability to convert bulkier substrates with unprecedented conversions, leading to the production of valuable chiral synthons like (+)-(R)-1,2,3,4-tetrahydroquinoline-4-ol and (+)-(1S,2R)-3-(pyridin-2-yl)cyclohexa-3,5-diene-1,2-diol with high yields and enantiomeric excess. The experiments utilized site-directed mutagenesis, biotransformations in recombinant E. coli strains, and analyses including HPLC-DAD, HPLC-ESI-MS, chiral HPLC-DAD, and NMR spectroscopy for product identification, quantification, and characterization.

Investigation of the Catalytic Activity of a 2-Phenylidenepyridine Palladium(II) Complex Bearing 4,5-Dicyano-1,3-bis(mesityl)imidazol-2-ylidene in the Mizoroki-Heck Reaction

10.1002/zaac.201500625

The study investigates the catalytic activity of two palladium(II) complexes, [PdCl(ppy)(IMes)] (4) and [PdCl(ppy){(CN)2IMes}] (6), in the Mizoroki-Heck reaction, a crucial cross-coupling reaction in the synthesis of pharmaceuticals and natural products. These complexes feature different N-heterocyclic carbene (NHC) ligands, IMes and (CN)2IMes, with the latter having a higher π-acceptor strength. The purpose of the study is to evaluate how the π-acceptor strength of the NHC ligands affects the catalytic performance of the complexes. The chemicals used include palladium(II) chloride, 2-phenylpyridine, 1,3-bis(mesityl)imidazol-2-ylidene (IMes), 4,5-dicyano-1,3-bis(mesityl)imidazol-2-ylidene ((CN)2IMes), and aryl halides, which serve as substrates in the Mizoroki-Heck reaction. The study aims to develop more effective precatalysts for this reaction by understanding the influence of the NHC ligands' electronic properties on the reaction's efficiency.

Bicyclo<2.2.1>heptanes in Organic Synthesis. Total Synthesis of the 16-Membered Ring Macrolide Tylonolide Hemiacetal: Synthesis and Coupling of the C(3)-C(9) and C(11)-C(17) Fragments

10.1021/ja00385a038

The research involves two separate studies. The first study focuses on the total synthesis of the 16-membered ring macrolide antibiotic tylonolide hemiacetal. Key chemicals used in this research include chiral bicyclo[2.2.1]heptenol, which was elaborated into the C(3)-C(9) and C(11)-C(17) fragments through a series of complex organic reactions involving reagents such as benzyl chloride, boron trifluoride etherate, lithium aluminum hydride, and m-chloroperbenzoic acid. The synthesis also utilized various solvents like methylcyclohexane and tetrahydrofuran, and involved steps like benzoylation, olefin inversion, and allylic oxidation to ultimately achieve the coupling of the fragments and the formation of the 16-membered macrolide ring. The second study investigates the photochemical formation of tetracarbonyl(4,4’-dialkyl-2,2’-bipyridine)metal from hexacarbonylmetal using rapid-scan Fourier transform infrared spectroscopy. Chemicals such as W(CO)6, 4,4’-(n-C19H39)2-2,2’-bpy, and 2-phenylpyridine were used to observe the formation of monodentate intermediates in the reaction. The study provides direct infrared spectral evidence for the formation of these intermediates, highlighting the role of CO and the bipyridine ligands in the photochemical process.

Cyclometalated Iridium(III) complexes of azadipyrromethene chromophores

10.1021/om4007032

The research, investigates the synthesis, properties, and potential applications of cyclometalated iridium(III) complexes incorporating azadipyrromethene ligands. The purpose of this study is to combine the visible excitability of azadipyrromethenes with the triplet-state photoproperties of iridium(III) complexes, aiming to create new materials with desirable optical and electrochemical properties for applications in areas such as light-emitting diodes (OLEDs), metal ion sensors, and biological tags. The researchers used base-assisted transmetalation from boron to synthesize a series of iridium(III) complexes with various cyclometalating ligands, such as 2-phenylpyridine (ppy), p-tolylpyridine (tpy), and 2-phenylbenzothiazole (bt), and azadipyrromethene ligands like LaBr2. The resulting complexes were characterized by various techniques, including X-ray crystallography, cyclic voltammetry, and density functional theory (DFT) calculations. The key findings include the preservation of the common four-aryl geometry of azadipyrromethenes in the six-coordinate iridium(III) complexes, the dominance of azadipyrromethene absorption bands in the optical spectra, and the identification of the azadipyrromethene as the site of one-electron reduction. The study concludes that these new complexes exhibit electroactive properties with reversible reductions and oxidations, and their optical properties are mainly governed by the azadipyrromethene ligand. The results suggest that the electrooptical properties of azadipyrromethene ligands could be extended to other metal complexes and materials, opening up new possibilities for the development of functional materials.

Tris-heteroleptic Iridium Complexes Based on Cyclometalated Ligands with Different Cores

10.1021/acs.inorgchem.7b01307

The research focuses on the synthesis and characterization of a series of tris-heteroleptic iridium complexes based on cyclometalated ligands with different cores, specifically [Ir(C^N1)(C^N2)(acac)] complexes, where C^N1 and C^N2 are 2-phenylpyridine (ppy), 2-(2,4-difluorophenyl)pyridine (dFppy), 1-phenylpyrazole (ppz), and 1-(2,4-difluorophenyl)pyrazole (dFppz). The purpose of this study was to explore how the structure of these complexes, particularly the positioning of substituents, affects their photophysical and electrochemical properties. The researchers found that while the overall architecture of the complex primarily dictates static properties such as absorption and emission spectra and redox potentials, dynamic properties like excited-state lifetime and radiative and nonradiative rate constants are sensitive to the specific positioning of the substituents.

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