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

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

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 
• 581-49-7 anatabine 
• 2743-90-0 (+/-)-Anatabine 
• 494-52-0 Anabasine 
• 110-86-1 pyridine 
• 93845-11-5 C₁₉H₁₄N₂O₂ 
• 30435-62-2 C₁₉H₁₄N₂O₂ 
• 626-60-8 3-Chloropyridine 
• 71257-51-7 3-pyridyl phenyl sulfoxide 
• 21970-13-8 (pyridin-2-yl)magnesium bromide 
• 626-55-1 3-Bromopyridine 
• 65007-00-3 pyridin-2-yl trifluoromethanesulfonate 
• 109-04-6 2-bromo-pyridine 
• 350-03-8 methyl-3-pyridylketone 

Downstream Products

• 59-67-6 nicotinic acid 
• 134529-13-8 1'-(2-(4-nitrophenyl)ethyl)-2,3'-bipyridinium iodide 
• 38700-88-8 m-chlorophenyl phenylsulfide 
• 38700-88-8 1-Chloro-3-phenylsulfanyl-benzene 
• 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 

Relevant articles and documents

Investigation of the possible pharmacologically active forms of the nicotinic acetylcholine receptor agonist anabaseine

Three major forms of the nicotinic agonist toxin anabaseine (cyclic iminium, cyclic imine and the monocationic open-chain ammonium-ketone) co-exist in almost equal concentrations at physiological pH.We asked the question: Which of these forms is pharmacologically active? First, we investigated the pH dependence of anabaseine inhibition of [3H]-methylcarbamylcholine binding at rat brain α4β2 nicotinic acetylcholine receptors (nAChRs). These experiments indicated that one or both monocationic forms interact with the orthosteric binding site for ACh. However, since they occur at equal concentrations near physiological pH, we employed another approach, preparing a stable analog of each form and examining its agonist activities and binding affinities at several vertebrate brain and neuromuscular nAChRs. Only 2-(3-pyridyl)-1,4,5,6-tetrahydropyrimidine monohydrogen chloride (PTHP), the cyclic iminium analog, displayed nAChR potencies and binding affinities similar to anabaseine. The cyclic imine analog 2,3'-bipyridyl and the open-chain ammonium-ketone analog 5-methylamino-1-(3-pyridyl)-1-pentanone (MAPP), displayed ≤1% of the activity predicted if the one form was solely active. The lower potency of weakly basic 2,3'-bipyridyl can be explained by the presence of a small concentration of its monocationic form. Since the open chain ammonium-ketone monocationic form of anabaseine has some structural similarity to the neurotransmitter GABA, we also tested the ability of anabaseine and its 1,2-dehydropyrrolidinyl analog myosmine to activate a mammalian GABAA receptor, but no activity was detected. We conclude that the monocationic cyclic iminium is the form which avidly binds and activates vertebrate nAChRs.

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,

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Ligand-to-metal charge transfer of a pyridine surface complex on TiO2for selective dehydrogenative cross-coupling with benzene

Dehydrogenative cross-coupling (DCC) between pyridine and benzene proceeded selectively using a TiO2 photocatalyst under visible light irradiation at optimized concentrations of the substrates. Visible light induces ligand-to-metal charge transfer (LMCT) between pyridine and a TiO2 surface to give a pyridine radical cation, which produces a pyridyl radical by its deprotonation or oxidation of another pyridine molecule. The pyridyl radical attacks a benzene ring to form an sp2C-sp2C bond and a hydrogen atom is subsequently removed to complete DCC. Selective excitation of the pyridine LMCT complex in the presence of an excess amount of benzene would be the key for higher selectivity. This journal is

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.

Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings

Despite the tremendous utilities of metal-mediated cross-couplings in modern organic chemistry, coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking – coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, we report a sulfur (IV) mediated cross-coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion.

Visible-light photoexcitation of pyridine surface complex, leading to selective dehydrogenative cross-coupling with cyclohexane

Upon photoirradiation with visible light, a pyridine molecule adsorbed on a TiO2 surface can be photoexcited to give a pyridine radical cation via ligand-to-metal charge transfer (LMCT) between pyridine and titanium. This leads to dehydrogenative cross-coupling (DCC) between pyridine and cyclohexane with concomitant hydrogen evolution. Since the radical cation can selectively oxidize cyclohexane to a cyclohexyl radical, the cross-coupling between pyridine and cyclohexane proceeds with higher selectivity compared with that in photocatalysis by TiO2 under UV irradiation.

Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides

Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon-carbon bonds in the pharmaceutical industry, the Suzuki-Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfinates, a cross-coupling process of unrivalled scope and utility is realized. The corresponding 3-And 4-substituted pyridine variants are also efficient coupling partners. In addition, we apply these sulfinates in a library format to the preparation of medicinally relevant derivatives of the drugs varenicline (Chantix) and mepyramine (Anthisan).