4,4'-Bipyridine

Base Information

• Chemical Name: 4,4'-Bipyridine
• CAS No.: 553-26-4
• Molecular Formula: C10H8N2
• Molecular Weight: 156.187
• Hs Code.: 2933.39 DERIVATION
• European Community (EC) Number: 209-036-3,628-542-9
• NSC Number: 404423
• UNII: X4O2OD61CB
• DSSTox Substance ID: DTXSID2027200
• Nikkaji Number: J45.972K
• Wikipedia: 4,4%27-Bipyridine,4'-Bipyridine
• Wikidata: Q229839
• Metabolomics Workbench ID: 54306
• ChEMBL ID: CHEMBL1374568
• Mol file: 553-26-4.mol

Synonyms:4,4'-bipyridine;4,4'-bipyridyl;4,4'-bipyridyl dihydrochloride;4,4'-dipyridyl

Chemical Property of 4,4'-Bipyridine

Chemical Property:

• Appearance/Colour: off-white to tan powder
• Melting Point: 109-112 °C(lit.)
• Refractive Index: 1.6057 (estimate)
• Boiling Point: 304.8 °C at 760 mmHg
• PKA: pK1:3.17(+2);pK2:4.82(+1) (25°C)
• Flash Point: 104.3 °C
• PSA: 25.78000
• Density: 1.106 g/cm³
• LogP: 2.14360
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: 4.5g/l
• Water Solubility.: slightly soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.068748264
• Heavy Atom Count: 12
• Complexity: 108

Purity/Quality:

99% ^*data from raw suppliers

4,4''-Dipyridyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38-20/21-23/24/25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CN=CC=C1C2=CC=NC=C2
• General Description: 4,4'-Bipyridine is a versatile bipyridyl ligand commonly used in coordination chemistry and supramolecular assembly, forming complexes with metals like rhodium(I) and serving as a building block for constructing mono-, bi-, and three-dimensional metallosupramolecular structures. It also participates in unexpected ligand transfer reactions and influences structural outcomes based on its coordination behavior. Additionally, it has been employed in studies involving molecular adsorption and catalysis, demonstrating its utility in diverse chemical applications.

Technology Process of 4,4'-Bipyridine

There total 116 articles about 4,4'-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: 91.0%

4-bromopyridin (1120-87-2) → 4,4'-bipyridine (553-26-4)

Guidance literature:

With tetraethylammonium tosylate; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; Ambient temperature; electrolysis;

DOI:10.1016/S0040-4039(00)98576-9

Reference yield: 88.0%

4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Guidance literature:

With potassium phosphate; In 1,4-dioxane; at 85 ℃; for 3h; Catalytic behavior; Green chemistry;

DOI:10.1002/aoc.5778

Reference yield: 85.0%

4-bromopyridin (1120-87-2) + 4-pyridylboronic acid (1692-15-5) → 4,4'-bipyridine (553-26-4)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In water; at 60 - 70 ℃; for 6h; Green chemistry;

DOI:10.1016/j.apcata.2013.01.021

upstream raw materials:

pyridine

4,4'-bipiperidine

1,1'-Diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine

lead(IV) tetraacetate

Downstream raw materials:

ethyl viologen

1,1'-Diacetyl-1,1'-dihydro-4,4'-bipyridin

1,1'-bibenzyl-[4,4']bipyridyldiium; dichloride

N,N'-diethyl-4,4'-bipyridinium iodide

Refernces

Is there a radical intermediate in the (salen)Mn-catalyzed epoxidation of alkenes?

10.1002/anie.199717231

The research focuses on the mechanism of (salen)Mn-catalyzed epoxidation of alkenes, a reaction of significant interest in the field of organic chemistry. The study aims to determine whether the reaction proceeds via a concerted manner, a radical intermediate, or a manganaoxetane intermediate. Through semi-empirical calculations and experiments involving substituted styrenes, the researchers concluded that the most viable mechanism involves an initial reversible formation of a metallaoxetane, which may undergo metal-carbon bond homolysis to relieve steric crowding and form a stabilized radical. This mechanism was supported by the survival of radical probes and the nonlinear Eyring effects observed. The chemicals used in the process include various metal salts (Co, Ni, Zn), 4,4'-bipyridine (4,4'-bpy), and other reagents such as acetone, ethanol, and nitrate anions. The study also explores the potential for these coordination polymers to adsorb small gaseous molecules like CH4, N2, and O2, highlighting their potential applications in molecular adsorption and catalysis.

New rhodium(I) supramolecular structures containing pyridyl and bipyridyl ligands

10.1016/j.jorganchem.2009.08.014

The research explores the self-assembly of rhodium(I) metallosupramolecular structures using [RhCl(CO)2]2 as an acceptor unit. Key chemicals involved in the research include [RhCl(CO)2]2, alkynylgold complex [Au(C?CC5H4N)(CNC6H4O(O)CC6H4OC10H21)], 4-ethynylpyridine, 4,4'-bipyridine, and diphosphines such as 1,4-bis(diphenylphosphino)butane (dppb) and 1,1-bis-(diphenylphosphino)methane (dppm). The study investigates the formation of various rhodium complexes through reactions with these chemicals, resulting in the creation of mono-, bi-, and three-dimensional structures. Notably, an unexpected isonitrile transfer from gold to rhodium centers was observed, and the influence of diphosphine bite angles on the final product structures was demonstrated. The research also includes the use of PM3 semi-empirical methods to optimize the geometry of the synthesized compounds, particularly focusing on the potential applications of these structures in catalysis and molecular recognition.