581-50-0

Basic information

• Product Name: 2,3'-Bipyridine
• Synonyms: 2-(Pyridin-3-yl)-pyridine;2-(3-pyridyl)pyridine;BP11592,3'-Bipyridine;2,3’-dipyridine;2,3'-Dipyridine;alpha,beta’-bipyridine;alpha,beta'-Bipyridine;alpha,beta-Dipyridyl
• CAS NO: 581-50-0
• Molecular Formula: C10H8N2
• Molecular Weight: 156.18
• EINECS: 209-468-2
• Product Categories: Metabolites;Nicotine Derivatives
• Mol File: 581-50-0.mol
• Article Data: 76

Chemical Properties

• Melting Point: 30-32 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 102-104°C@0.7 torr
• Flash Point: 111.4 °C
• Appearance: pale yellow oil
• Density: 1.1400
• Vapor Pressure: 0.00271mmHg at 25°C
• Refractive Index: 1.6223
• Storage Temp.: -20°C Freezer
• PKA: pK1:1.52(+2);pK2:4.42(+1) (20°C)
• CAS DataBase Reference: 2,3'-Bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3'-Bipyridine(581-50-0)
• EPA Substance Registry System: 2,3'-Bipyridine(581-50-0)

Safety Data

• RIDADR: 1993
• HazardClass: 3
• PackingGroup: Ⅲ
• Hazardous Substances Data: 581-50-0(Hazardous Substances Data)

Usage

Description

2,3'-Bipyridine is an alkaloid compound that is obtained as a colorless, viscous oil which is optically inactive and has a density of 1.0984. It is freely soluble in most organic solvents but only slightly soluble in water or light petroleum. The molecular structure of 2,3'-Bipyridine consists of two pyridine rings connected by a carbon-carbon bond at the 2nd and 3rd positions.

Uses

Used in Chemical Synthesis:
2,3'-Bipyridine is used as a building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes. Its unique structure allows for the formation of stable complexes with metal ions, making it a versatile component in the development of coordination compounds.
Used in Analytical Chemistry:
2,3'-Bipyridine is used as a chelating agent in analytical chemistry for the detection and quantification of metal ions. Its ability to form stable complexes with metal ions allows for the selective and sensitive determination of trace metal concentrations in various samples.
Used in Environmental Applications:
2,3'-Bipyridine is used as an extractant in environmental applications for the removal of heavy metal ions from contaminated water and soil. Its high affinity for metal ions enables efficient extraction and separation processes, contributing to the remediation of polluted environments.
Used in Materials Science:
2,3'-Bipyridine is used as a ligand in the synthesis of coordination polymers and metal-organic frameworks (MOFs). These materials exhibit unique properties, such as high surface area, porosity, and tunable functionality, making them promising candidates for applications in gas storage, catalysis, and sensing.

References

Noga., Chern. Zentr., I, 434 (1915) Spath, Biniecki., Ber., 72, 1809 (1939)

InChI:InChI=1/C10H8N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-8H

Upstream product

• 3731-52-0 3-Aminomethylpyridine 
• 690255-50-6 [2,3']bipyridyl-3,2'-dicarboxylic acid 
• 581-49-7 anatabine 
• 2743-90-0 (+/-)-Anatabine 
• 494-52-0 Anabasine 
• 110-86-1 pyridine 
• 93845-11-5 C₁₉H₁₄N₂O₂ 
• 30435-62-2 C₁₉H₁₄N₂O₂ 
• 60573-68-4 3-pyridyllithium 
• 109-04-6 2-bromo-pyridine 
• 626-60-8 3-Chloropyridine 
• 109-09-1 2-chloropyridine 
• 89878-14-8 3-Diethylboranylpyridine 
• 1120-90-7 3-iodopyridine 

Downstream Products

• 562098-24-2 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,2′-bipyridine 
• 85237-62-3 (+/-)-1'-Methyl-1',2',3',4',5',6'-hexahydro-[2,3']bipyridyl 
• 134529-14-9 1-methyl-1'-(2-(4-nitrophenyl)ethyl)-2,3'-bipyridinium diiodide 
• 861907-77-9 1-benzyl-3-(pyridin-2-yl)piperidine 
• 38700-88-8 1-Chloro-3-phenylsulfanyl-benzene 
• 38700-88-8 m-chlorophenyl phenylsulfide 
• 134529-13-8 1'-(2-(4-nitrophenyl)ethyl)-2,3'-bipyridinium iodide 
• 59-67-6 nicotinic acid 

Relevant articles and documents

-

-

-

-

Continuous Flow as Enabling Technology: Synthesis of Heteroaromatic Sulfinates as Bench Stable Cross-Coupling Partners

An enabling continuous flow setup for handling of unstable organolithium intermediates and synthesis of heteroaryl sulfinates on a multigram scale is described. The developed continuous flow process allows for the synthesis and simple isolation of heteroaryl sulfinates which are otherwise challenging to access in classical batch mode. The lithium sulfinate salts prepared by this method were shown to be efficient reaction partners in palladium catalyzed C(sp2)-C(sp2) cross-coupling to access medicinally relevant bis-heteroaryl motifs.

Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6

S-(-)-Nicotine and 13 of the most prevalent nicotine-related alkaloids and metabolites (i.e., S-(-)-nornicotine, myosmine, β-nicotyrine, S-cotinine, S-norcotinine, S-(-)-nicotine N-1′-oxide, S-(-)-nicotine Δ 1′-5′-iminium ion, S-(-)-anabasine,

-

-

Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts

Herein are reported ligand-coupling reactions of Grignard reagents with pyridylsulfonium salts. The method has wide functional group tolerance and enables the formation of bis-heterocycle linkages, including 2,4′-, 2,3′-, and 2,2′-bipyridines, as well as pyridines linked to pyrimidines, pyrazines, isoxazoles, and benzothiophenes. The methodology was successfully applied to the synthesis of the natural products caerulomycin A and E.

Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines

An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.