4,4'-Diphenyl-2,2'-bipyridine

Base Information

• Chemical Name: 4,4'-Diphenyl-2,2'-bipyridine
• CAS No.: 6153-92-0
• Molecular Formula: C22H16N2
• Molecular Weight: 308.382
• Hs Code.: 2933399090
• European Community (EC) Number: 228-174-5
• DSSTox Substance ID: DTXSID5064128
• Nikkaji Number: J211.423B
• Wikidata: Q81991270
• Mol file: 6153-92-0.mol

Synonyms:4,4'-Diphenyl-2,2'-bipyridine;6153-92-0;4,4'-Diphenyl-2,2'-dipyridyl;4-phenyl-2-(4-phenylpyridin-2-yl)pyridine;2,2'-Bipyridine, 4,4'-diphenyl-;EINECS 228-174-5;4-phenyl-2-(4-phenyl(2-pyridyl))pyridine;TimTec1_001955;SCHEMBL417290;DTXSID5064128;3-Methyl-2-trifluoromethylindole;HMS1539I19;AKOS003234729;AS-59799;CS-0012229;FT-0636001;4,4'-Diphenyl-2,2'-dipyridyl, technical grade;4,4'-Diphenyl-2,2'-dipyridyl, 2,2'-Bipyridine;A833286;W-203295;BRD-K51847055-001-01-9

Chemical Property of 4,4'-Diphenyl-2,2'-bipyridine

Chemical Property:

• Melting Point: 188-190 °C(lit.)
• Boiling Point: 475.2 °C at 760 mmHg
• PKA: 4.49±0.30(Predicted)
• Flash Point: 181.2 °C
• PSA: 25.78000
• Density: 1.134 g/cm³
• LogP: 5.47760
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 308.131348519
• Heavy Atom Count: 24
• Complexity: 334

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,4'-Diphenyl-2,2'-bipyridine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=NC=C2)C3=NC=CC(=C3)C4=CC=CC=C4

Technology Process of 4,4'-Diphenyl-2,2'-bipyridine

There total 11 articles about 4,4'-Diphenyl-2,2'-bipyridine 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: 93.0%

4,4'-dibromo-2,2'-bipyridine (18511-71-2) + phenylboronic acid (98-80-6) → 4,4'-diphenyl-2,2'-bipyridine (6153-92-0)

Guidance literature:

4,4'-dibromo-2,2'-bipyridine; phenylboronic acid; With sodium carbonate; In water; toluene; for 0.25h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; toluene; for 14h; Reflux;

DOI:10.1021/ic101909e

Reference yield: 78.0%

p-phenylpyridine (939-23-1) → 4,4'-diphenyl-2,2'-bipyridine (6153-92-0)

Guidance literature:

p-phenylpyridine; With [{(MeCN-2,6-ⁱPr₂C₆H₃)₂CH}Mg(2,2,6,6-tetramethylpiperidine)]; In tetrahydrofuran; at 70 ℃; Inert atmosphere;

DOI:10.1002/chem.201803297

Reference yield: 68.0%

4-Phenylpyridine 1-oxide (1131-61-9) → 4,4'-diphenyl-2,2'-bipyridine (6153-92-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); potassium tert-butylate; In 2-methyltetrahydrofuran; at 65 ℃; for 3.16667h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6cc04816a

upstream raw materials:

2-bromo-4-phenylpyridine

biphenyl

p-phenylpyridine

4-phenyl-pyridin-2-ylamine

Downstream raw materials:

{bis(1,10-phenanthroline)(4,4'-diphenyl-2,2'-bipyridine)ruthenium(II)}Cl₂

Refernces

• 1、 Davin, Laia,Clegg, William,Kennedy, Alan R.,Probert, Michael R.,McLellan, Ross,Hevia, Eva. "Structural and Synthetic Insights into Pyridine Homocouplings Mediated by a β-Diketiminato Magnesium Amide Complex". supporting information. p. 14830 - 14835. Retrieved 2018/09/25.
• 2、 Stephens, David E.,Lakey-Beitia, Johant,Burch, Jessica E.,Arman, Hadi D.,Larionov, Oleg V.. "Mechanistic insights into the potassium: Tert -butoxide-mediated synthesis of N-heterobiaryls". supporting information. p. 9945 - 9948. Retrieved 2016/08/11.