2,4'-Bipyridine

Base Information

• Chemical Name: 2,4'-Bipyridine
• CAS No.: 581-47-5
• Molecular Formula: C10H8N2
• Molecular Weight: 156.187
• Hs Code.: 29333990
• European Community (EC) Number: 209-467-7
• UNII: C6SN6RU851
• DSSTox Substance ID: DTXSID40206822
• Nikkaji Number: J147.228C
• Wikidata: Q209228
• ChEMBL ID: CHEMBL1867574
• Mol file: 581-47-5.mol

Synonyms:2,4'-dipyridyl

Chemical Property of 2,4'-Bipyridine

Chemical Property:

• Appearance/Colour: light yellow to beige-brown cystalline powder
• Melting Point: 58-62 ºC
• Refractive Index: 1.6057 (estimate)
• Boiling Point: 280-282 ºC
• PKA: pK1:1.19(+2);pK2:4.77(+1) (20°C)
• Flash Point: 105.7°C
• PSA: 25.78000
• Density: 1.106g/cm³
• LogP: 2.14360
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Sparingly), DMSO (Sparingly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.068748264
• Heavy Atom Count: 12
• Complexity: 130

Purity/Quality:

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

2,4''-Bipyridine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)C2=CC=NC=C2
• Uses: 2,4''-Bipyridine is used in preparation of Iridium Heterocyclic complexes.

Technology Process of 2,4'-Bipyridine

There total 81 articles about 2,4'-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: 98.0%

2-chloropyridine (109-09-1) + 4-pyridylboronic acid (1692-15-5) → 4-(2-pyridyl)pyridine (581-47-5)

Guidance literature:

With potassium phosphate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tricyclohexylphosphine; In 1,4-dioxane; water; at 100 ℃; for 18h;

DOI:10.1002/anie.200503479

Reference yield: 89.0%

6-chloro-2,4′-bipyridine (39883-34-6) → 4-(2-pyridyl)pyridine (581-47-5)

Guidance literature:

With potassium hydroxide; hydrogen; palladium on activated charcoal; In methanol; for 3h; under 760 Torr; Ambient temperature;

DOI:10.3987/COM-89-5283

Reference yield: 85.0%

2-bromo-pyridine (109-04-6) + 4-pyridineboronic acid pinacol ester (181219-01-2) → 4-(2-pyridyl)pyridine (581-47-5)

Guidance literature:

With tricyclohexylphosphine-copper chloride; sodium t-butanolate; In toluene; at 100 ℃; for 15h; Inert atmosphere; Sealed tube;

DOI:10.1039/c8cc03145b

upstream raw materials:

pyridine

dodecahydro-[2,4']bipyridinyl

4-(aminomethyl)pyridine

[2,4']bipyridyl-2',6'-dicarboxylic acid

Downstream raw materials:

iodure de 1-methyl-4-(2-pyridyl)pyridinium

1,1'-dimethyl-[2,4']bipyridyldiium; diiodide

Phenyl-(2-pyridin-2-yl-4a,5,10,11-tetraaza-benzo[b]fluoren-7-yl)-methanone

1',2',3',4',5',6'-hexahydro-2'H-[2,4'-bipyridine] dihydrochloride

Refernces

• 1、 Hishitani, Shinichiro,Naniwa, Shimpei,Yamamoto, Akira,Yoshida, Hisao. "Ligand-to-metal charge transfer of a pyridine surface complex on TiO2for selective dehydrogenative cross-coupling with benzene". . p. 11366 - 11373. Retrieved 2021/05/31.
• 2、 Horan, Alexandra M.,Duong, Vincent K.,McGarrigle, Eoghan M.. "Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts". supporting information. p. 9089 - 9093. Retrieved 2021/11/30.