5-Bromo-2-phenylpyridine

Base Information

• Chemical Name: 5-Bromo-2-phenylpyridine
• CAS No.: 27012-25-5
• Molecular Formula: C11H8BrN
• Molecular Weight: 234.095
• Hs Code.: 29333990
• European Community (EC) Number: 681-730-2
• DSSTox Substance ID: DTXSID50376520
• Nikkaji Number: J2.430.205I
• Wikidata: Q72511283
• Mol file: 27012-25-5.mol

Synonyms:5-bromo-2-phenylpyridine;27012-25-5;2-Phenyl-5-bromopyridine;MFCD04114181;5-bromo-2-phenyl-pyridine;3-BROMO-6-PHENYLPYRIDINE;SCHEMBL1182292;DTXSID50376520;PRNGIODVYLTUKH-UHFFFAOYSA-N;AKOS005216117;AB17945;BS-2050;CS-W014673;AMY202003263;SY055846;B5018;FT-0703190;A846194;J-516991;3-(2-Ethoxycarbonyl-ethyl)-5-methyl-1H-pyrrole-2-carboxylicacidethylester

Chemical Property of 5-Bromo-2-phenylpyridine

Chemical Property:

• Vapor Pressure: 0.00117mmHg at 25°C
• Melting Point: 73-75°C
• Refractive Index: 1.606
• Boiling Point: 309.3 °C at 760 mmHg
• PKA: 2.08±0.10(Predicted)
• Flash Point: 140.9 °C
• PSA: 12.89000
• Density: 1.426g/cm³
• LogP: 3.51110
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in ethyl ether.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 232.98401
• Heavy Atom Count: 13
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-2-phenylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC=C(C=C2)Br
• Uses: 5-Bromo-2-phenylpyridine is used as a ligand in coordination chemistry and reacts with iridium(III) chloride to get in tris-heteroleptic Iridium(III), which finds application as phosphorescent (triplet) emitters in organic light-emitting diodes (OLEDs) due to its self-emitting nature, fast response, wide viewing angle and low power consumption.

Technology Process of 5-Bromo-2-phenylpyridine

There total 31 articles about 5-Bromo-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: 99.0%

2-iodo-5-bromopyridine (223463-13-6) + phenylboronic acid (98-80-6) → 5-bromo-2-phenylpyridine (27012-25-5)

Guidance literature:

With potassium carbonate; In 1,2-dimethoxyethane; at 100 ℃; for 24h;

DOI:10.1039/d1ta00012h

Reference yield: 99.0%

2,5-dibromopyridine (624-28-2) + bromobenzene (108-86-1,52753-63-6) → 5-bromo-2-phenylpyridine (27012-25-5)

Guidance literature:

bromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; cyclohexane; at -78 ℃; for 0.5h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; hexane; cyclohexane; at -78 - 20 ℃; for 2.6h; Inert atmosphere;

2,5-dibromopyridine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; cyclohexane; for 16h; Inert atmosphere; Reflux;

DOI:10.1039/c1dt11236h

Reference yield: 97.0%

2,5-dibromopyridine (624-28-2) + phenylboronic acid (98-80-6) → 5-bromo-2-phenylpyridine (27012-25-5)

Guidance literature:

With palladium diacetate; potassium carbonate; triphenylphosphine; In methanol; acetonitrile; at 50 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2013.10.065

upstream raw materials:

2,5-dibromopyridine

bromobenzene

3-bromo-1-(phenoxycarbonyl)pyridinium chloride

5-bromo-1-phenoxycarbonyl-2-phenyl-1,2-dihydropyridine

Downstream raw materials:

2,5-diphenylpyridine

C₂₄H₁₇NO

5-ethynyl-2-phenylpyridine

2-phenyl-5-(2-(trimethylsilyl)ethynyl)pyridine

Refernces

• 1、 Liu, Jia,Chen, Zhongxin,Liu, Cuibo,Zhang, Bao,Du, Yonghua,Liu, Chen-Fei,Ma, Lu,Xi, Shibo,Li, Runlai,Zhao, Xiaoxu,Song, Jingting,Sui, Xin Zhi,Yu, Wei,Miao, Ling,Jiang, Jianjun,Koh, Ming Joo,Loh, Kian Ping. "Molecular engineered palladium single atom catalysts with an M-C1N3subunit for Suzuki coupling". supporting information. p. 11427 - 11432. Retrieved 2021/05/19.
• 2、 Fukazawa, Yasuaki,Rubtsov, Aleksandr E.,Malkov, Andrei V.. "A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides". supporting information. p. 3317 - 3319. Retrieved 2020/05/25.