15578-73-1

Basic information

• Product Name: 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL
• Synonyms: 2-(2-PIPERIDINYL)PYRIDINE;1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL;CHEMBRDG-BB 4002369;2-PIPERIDIN-2-YLPYRIDINE;2-piperidin-2-ylpyridine dihydrochloride;pyridine, 2-(2-piperidinyl)-;2-piperidin-2-ylpyridine(SALTDATA: 2HCl);2-(2-Piperidyl)pyridine
• CAS NO: 15578-73-1
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23
• Mol File: 15578-73-1.mol

Chemical Properties

• Boiling Point: 280℃
• Flash Point: 123℃
• Appearance: /
• Density: 1.014
• Vapor Pressure: 0.00378mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 2-8°C
• PKA: 8.88±0.10(Predicted)
• CAS DataBase Reference: 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL(15578-73-1)
• EPA Substance Registry System: 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL(15578-73-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 15578-73-1(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL is used as a ligand for forming stable complexes with metal ions, which is crucial in coordination chemistry. Its ability to chelate metals enhances the stability and reactivity of metal complexes, making it a valuable component in the synthesis of various coordination compounds.
Used in Catalysis:
In the field of catalysis, 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL is employed as a ligand to modify the properties of metal catalysts. Its coordination with metal ions can influence the catalytic activity and selectivity, which is essential for optimizing chemical reactions in industrial processes.
Used in Material Science:
1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL contributes to material science by participating in the development of new materials with unique properties. Its interaction with metal ions can lead to the formation of metal-organic frameworks or other composite materials with potential applications in areas such as gas storage, catalysis, and sensing.
Used in Medicinal Chemistry:
In medicinal chemistry, 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL is utilized in the design and synthesis of pharmaceutical compounds. Its chelating properties allow it to form complexes with therapeutically relevant metal ions, potentially enhancing the efficacy and delivery of drugs.
Used in Environmental Safety:
Given its known toxicity to aquatic organisms, 1,2,3,4,5,6-HEXAHYDRO-[2,2']BIPYRIDINYL is a subject of study in environmental chemistry. Understanding its impact and developing methods to mitigate its effects on aquatic ecosystems is crucial for ensuring environmental safety in chemical handling and disposal processes.

InChI:InChI=1/C10H14N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1,3,5,7,10,12H,2,4,6,8H2

Upstream product

• 366-18-7 [2,2]bipyridinyl 
• 33421-43-1 2,2'-bipyridyl N-oxide 
• 1061659-64-0 2-[1-(phenylmethyl)-2-piperidinyl]pyridine 
• 5414-21-1 5-bromopentan-1-nitrile 
• 17624-36-1 2-pyridyllithium 
• 53422-71-2 2-(3,4,5,6-tetrahydropyridin-2-yl)pyridine 

Downstream Products

• 1228934-83-5 4-(1H-indol-3-ylmethyl)-6-{2-oxo-2-[(2R)-2-pyridin-2-ylpiperidin-1-yl]ethyl}-1-phenyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one 
• 1424330-16-4 C₂₂H₂₂Cl₂N₄O₂ 
• 366-18-7 [2,2]bipyridinyl 

Relevant articles and documents

Design, synthesis, and evaluation of pyrrolidine based CXCR4 antagonists with in vivo anti-tumor metastatic activity

The chemokine receptor CXCR4 has been proposed as a drug target based on its important functions in HIV infection, inflammation/autoimmune diseases and cancer metastasis. Herein we report the design, synthesis and evaluation of novel CXCR4 antagonists based on a pyrrolidine scaffold. The structural exploration/optimization identified numerous potent CXCR4 antagonists, represented by compound 46, which displayed potent binding affinity to CXCR4 receptor (IC50 = 79 nM competitively displacing fluorescent 12G5 antibody) and inhibited CXCL12 induced cytosolic calcium flux (IC50 = 0.25 nM). Moreover, in a transwell invasion assay, compound 46 significantly mitigated CXCL12/CXCR4 mediated cell migration. Compound 46 exhibited good physicochemical properties (MW 367, logD7.4 1.12, pKa 8.2) and excellent in vitro safety profiles (e.g., hERG patch clamp IC50 > 30 μM and minimal CYP isozyme inhibition). Importantly, 46 displayed much improved metabolic stability in human and rat liver microsomes. Lastly, 46 demonstrated marked efficacy in a cancer metastasis model in mice. These results strongly support 46 as a prototypical lead for the development of promising CXCR4 antagonists as clinical candidates.

Reduction Regiospecifique des Bipyridines

A method for the specific reduction of bipyridines through the use of the N-oxo derivatives is described.

Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters

A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.

Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

The chiral base n-BuLi/(-)-sparteine or n-BuLi/(+)-sparteine surrogate promotes kinetic resolution of N-Boc-2-arylpiperidines by asymmetric deprotonation. The enantioenriched starting material was recovered with yields 39-48% and ers up to 97:3. On lithiation then electrophilic quench, 2,2-disubstituted piperidines were obtained with excellent yields and enantioselectivities.

Chiral ligand 2-(2′-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes

Chiral ligand 2-(2′-piperidinyl)pyridine 1 has been synthesized in good overall yield by sequential benzylation, hydrogenation and debenzylation of 2,2′-bipyridine. Its enantiomerically pure enantiomers have been obtained by resolution of 2-(1-benzyl-2-piperidinyl)pyridine 2 with d-tartaric acid (or l-tartaric acid) followed by debenzylation. The absolute configuration was determined by X-ray analysis of the (S)-2 d-tartrate. It was demonstrated that 1 can be used as an effective enantioselective catalyst in the addition of diethylzinc to aldehydes. Optically active secondary alcohols with up to 100% enantiomeric excess were obtained in high yields.

From bipyridines to tobacco alkaloids and related compounds

Starting from structural considerations which led to the hypothesis that a chemical relationship could exist between two families of natural compounds (mainly pyridinic and pyrrolidinic alkaloids), experiments were carried out in order to establish a correlation route between the two studied classes. Of special interest was the central position of nicotine in these studies, and the main part of this work was devoted to the synthesis of nicotine starting from bipyridines. It was thus necessary to determine the conditions for selective reactions on one aromatic ring of bipyridines (N-methylation, N-oxidation and reduction of the heterocycle). Ring contraction procedure allowed us to obtain nicotine from the parent compound (3,3′-bipyridine). Complementary studies yielded various isomers of piperidinylpyridines (hexahydro derivatives of bipyridines) in a regiochemically controlled manner by means of original methods. Elsevier,.

Complexes of polyhydro-2,2'-bipyridines with molybdenum and tungsten carbonyls

Reduction of 2,2'-bipyridine with tin in hydrochloric acid produces both 2-(2'-piperidinyl) pyridine and (1,2,3,6-tetrahydro)-2,2'-bipyridine, which have been characterised by (IR, NMR, and UV) spectroscopy.Tetracarbonyl-molybdenum and -tungsten complexes of these ligands exhibit a solvatochromic behaviour very similar to that of the analogous 2,2'-bipyridine complexes.Key words: Molybdenum; Tungsten; Solvatochromism; Charge transfer; Electronic; Bipyridine