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

Synonyms:2-phenylpyridine

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): Xi
• 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
• Uses: 2-Phenylpyridine has been studied as a dopamine d3 receptor selective ligand with potential application for treatment of drug addictions, schizophrenia and Parkinson’s disease. 2-Phenylpyridine for synthesis. CAS 1008-89-5, molar mass 155.2 g/mol.

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:

Reference yield: 92.0%

2-bromo-pyridine (109-04-6) + phenylboronic acid (98-80-6) → 2-phenylpyridine (1008-89-5) + [2,2]bipyridinyl (366-18-7)

Guidance literature:

With potassium phosphate; palladium diacetate; In water; at 100 ℃; for 4h; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.oprd.6b00180

Reference yield: 90.0%

α-phenyl-(2-(pyridin-2-yl))benzyl alcohol → 2-phenylpyridine (1008-89-5) + benzaldehyde (100-52-7)

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

Reference yield: 64.0%

2-iodopyridine (5029-67-4) + triethoxyphenylsilane (780-69-8) → 2-phenylpyridine (1008-89-5) + [2,2]bipyridinyl (366-18-7)

Guidance literature:

With copper(l) iodide; cesium fluoride; In N,N-dimethyl-formamide; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol402701x

upstream raw materials:

pyridine

benzenediazonium

N-nitrosoacetanilide

1-methyl-4-nitrosobenzene

Downstream raw materials:

2-(2,6-dideuterophenyl)pyridine

2-Picolinic acid

1,2-di(pyridin-2-yl)benzene

Refernces

• 1、 Canich, Jo Ann M.,Hagadorn, John R.,Kulyabin, Pavel S.,Uborsky, Dmitry V.,Voskoboynikov, Alexander Z.. "Pyridylamido hafnium complexes with a silylene bridge: Synthesis and olefin polymerization". . p. 6693 - 6702. Retrieved 2020.
• 2、 Kumar, Arvind,Shah, Bhahwal Ali. "Synthesis of Biaryls via Benzylic C-C Bond Cleavage of Styrenes and Benzyl Alcohols". . p. 5232 - 5235. Retrieved 2015.
• 3、 Gómez-Martínez, Melania,Buxaderas, Eduardo,Pastor, Isidro M.,Alonso, Diego A.. "Palladium nanoparticles supported on graphene and reduced graphene oxide as efficient recyclable catalyst for the Suzuki-Miyaura reaction of potassium aryltrifluoroborates Dedicated to the memory of Prof. Carlos F. Barbas III.". . p. 1 - 7. Retrieved 2015.
• 4、 Yoshikai, Naohiko,Mashima, Hiroko,Nakamura, Eiichi. "Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with Grignard reagents under nickel/magnesium bimetallic cooperation". . p. 17978 - 17979. Retrieved 2005.
• 5、 Gholinejad, Mohammad,Shahsavari, Hamid R.. "N,N′-bis(2-pyridinecarboxamide)-1,2-benzene palladium complex as a new efficient catalyst for Suzuki-Miyaura coupling reaction under phosphane free conditions Dedicated to Professor Mehdi Rashidi". . p. 433 - 438. Retrieved 2014.
• 6、 Shi, Qiang,Chen, Chuan-Feng. "Switchable Complexation between (O-Methyl)6-2,6-helic[6]arene and Protonated Pyridinium Salts Controlled by Acid/Base and Photoacid". . p. 3175 - 3178. Retrieved 2017.
• 7、 Chen, Ming-Tsz,Lin, Yu-Hsuan,Jian, Kun-Han. "(N-Heterocyclic carbene) ion-pair palladium complexes: Suzuki–Miyaura cross-coupling studies in neat water under mild conditions". . . Retrieved 2020.
• 8、 Senter,Rumple,Medina-Ramos,Houle,Cheng,Gelbaum,Fisk,Holden,Pollet,Eckert,Liotta, Charles L.. "The effects of CO2pressure and pH on the Suzuki coupling of basic nitrogen containing substrates". . p. 7598 - 7602. Retrieved 2014.
• 9、 Abramovitch,Giam. "-". . p. 3127,3130. Retrieved 1963.
• 10、 De Tovar, Jonathan,Rataboul, Franck,Djakovitch, Laurent. "From the grafting of NHC-based Pd(II) complexes onto TiO2 to the in situ generation of Mott-Schottky heterojunctions: The boosting effect in the Suzuki-Miyaura reaction. Do the evolved Pd NPs act as reservoirs?". . p. 133 - 147. Retrieved 2021.