179873-48-4

Basic information

• Product Name: 2,2'-BIPYRIDINE-5-CARBALDEHYDE
• Synonyms: 2,2'-BIPYRIDINE-5-CARBALDEHYDE;6-pyridin-2-ylpyridine-3-carbaldehyde
• CAS NO: 179873-48-4
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.19
• Mol File: 179873-48-4.mol

Chemical Properties

• Melting Point: 91.8-93.0 °C
• Boiling Point: 355.8±32.0 °C(Predicted)
• Appearance: /
• Density: 1.205±0.06 g/cm3(Predicted)
• PKA: 3.65±0.22(Predicted)
• CAS DataBase Reference: 2,2'-BIPYRIDINE-5-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-BIPYRIDINE-5-CARBALDEHYDE(179873-48-4)
• EPA Substance Registry System: 2,2'-BIPYRIDINE-5-CARBALDEHYDE(179873-48-4)

Safety Data

• Hazardous Substances Data: 179873-48-4(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
2,2'-Bipyridine-5-carbaldehyde is used as a chelating ligand for forming coordination complexes with metal ions, playing a crucial role in coordination chemistry.
Used in Catalytic Systems:
2,2'-Bipyridine-5-carbaldehyde is used as a component in the synthesis of catalytic systems, contributing to their development and enhancing their performance.
Used in Organic Light-Emitting Diodes (OLEDs):
2,2'-Bipyridine-5-carbaldehyde is utilized in the creation of organic light-emitting diodes, where its properties contribute to the device's efficiency and performance.
Used in Sensor Technology:
2,2'-Bipyridine-5-carbaldehyde is employed as a sensor for detecting metal ions and other analytes, capitalizing on its coordination ability to selectively bind and signal the presence of target species.
Used in Organic Synthesis:
2,2'-Bipyridine-5-carbaldehyde is used as a versatile building block in organic synthesis, allowing for the introduction of different substituents and enabling the development of a wide range of chemical compounds and materials.

Upstream product

• 98007-15-9 5-bromomethyl-2,2'-bipyridine 
• 26482-00-8 1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide 
• 220904-17-6 2-bromo-5-[1,3]dioxolan-2-yl-pyridine 
• 149806-06-4 6-bromonicotinaldehyde 
• 15862-19-8 5-bromo-2,2'-bipyridyl 
• 21543-49-7 2-Chloro-5-hydroxymethylpyridine 
• 23100-12-1 6-chloronicotinylaldehyde 
• 17997-47-6 2-tri-n-butylstannylpyridine 
• 109-04-6 2-bromo-pyridine 
• 127-09-3 sodium acetate 
• 56100-20-0 5-methyl-2,2'-bipyridine 
• 1122-62-9 2-acetylpyridine 

Downstream Products

• 162318-34-5 5-ethynyl-2,2'-bipyridine 
• 945529-37-3 C₆H₅CHCHC₆H₂(OC₈H₁₇)2CHCHC₅H₃NC₅H₄N 
• 945529-35-1 5-{(E)-2-[2,5-Bis-octyloxy-4-((E)-2-pyren-1-yl-vinyl)-phenyl]-vinyl}-[2,2']bipyridinyl 

Relevant articles and documents

Ruthenium-based phosphorescent probe for selective and naked-eye detection of cyanide in aqueous media

A simple molecular phosphorescent Ru(II) probe P1 has been synthesized by the reaction of 5-aldehyde-2,2′-bipyridine with ruthenium(II) chlorides under mild conditions. The probe upon interaction with different cation and anion showed high selectivity and sensitivity for cyanide ion (CN?) through phosphorescence “turn-on” response in aqueous solution (60% water) with a detection limit of 0.75 μM. The significant phosphorescence enhancement (~ 30-fold) is attributed to the nucleophilic addition of cyanide ion to the aldehyde groups of the ruthenium complex in 3 : 1 stoichiometry, in which a naked-eye sensitive orange red color of solution changed to a yellow. The generation of cyanohydrin species through nucleophilic addition has been confirmed by 1H NMR, FT-IR and mass spectra. Based on the color change of the solution, a visual colorimetric strip was prepared, which also showed good detection performance on cyanide ion with quick response time. The prominent efficiency of the Ru(II) probe proved the potential possibility of application in biosystems relating with cyanide ion.

A miniaturized voltammetric pH sensor based on optimized redox polymers

A miniaturized pH sensor based on the voltammetric determination of the potential difference between a pH dependent toluidine blue O modified redox polymer and a pH independent osmium complex modified redox polymer was developed. Gold micro electrodes of various dimensions were modified with the two redox polymers by non-manual deposition procedures. Square wave voltammetry was used to determine the oxidation potentials of the polymer bound redox species allowing the precise determination of the pH value of the electrolyte solution without the need of a stable reference electrode.

Synthesis of Hetero-multinuclear Metal Complexes by Site-Selective Redox Switching and Transmetalation on a Homo-multinuclear Complex

Hetero-multinuclear metal complexes are a promising class of compounds applicable to photoluminescence, magnetism, and catalysis. In this work, we have developed a synthetic method for hetero-tetranuclear metal complexes by combining advantages of site-selective redox switching and transmetalation. First, a homo-tetranuclear CoII4 complex was converted to a mixed-valence CoIIICoII3 complex by site-selective oxidation, which was then transmetalated from CoII to NiII to form a heterometallic CoIIINiII3 complex. Finally, a CoIINiII3 complex was synthesized by metal-selective reduction on the CoIII site. The basic structural frameworks of the main products in the whole process starting from the CoII4 complex are isostructural. Notably, the CoIINiII3 complex was not accessible by direct mixing of ligand, CoII, and NiII. This method would provide an alternative strategy for highly selective synthesis of hetero-multinuclear metal complexes.

Copper(II)-induced Fluorescence Quenching of a BODIPY Fluorophore

The ongoing developments in fluorescence microscopy have pushed the interest in new fluorescent probes with specific properties. Aside of controlling emissive states by light irradiation, defined control by changing the chemical environment has come into focus. In this context, we designed a fluorescent probe by conjugation of bipyridine, acting as sensor for CuII, to a BODIPY derivative at the shortest possible distance between sensor and chromophore. Herein, we present the synthesis of the BODIPY probe along with its crystal structure. We found a strong dependence of absorption and emission upon CuII complex formation decreasing the fluorescence quantum yield to ca. 1 % in respect to the pure probe. We hypothesize that further functionalization with a linker could make this compound and interesting probe for fluorescence microscopy.

Toward anticancer gold-based compounds targeting PARP-1: A new case study

A new gold(iii) complex bearing a 2-((2,2′-bipyridin)-5-yl)-1H-benzimidazol-4-carboxamide ligand has been synthesized and characterized for its biological properties in vitro. In addition to showing promising antiproliferative effects against human cancer cells, the compound potently and selectively inhibits the zinc finger protein PARP-1, with respect to the seleno-enzyme thioredoxin reductase. The results hold promise for the design of novel gold-based anticancer agents disrupting PARP-1 function and to be used in combination therapies.

Encapsulation of metalloporphyrins in a self-assembled cubic M 8L6 cage: A new molecular flask for cobalt-porphyrin- catalysed radical-type reactions

The synthesis of a new, cubic M8L6 cage is described. This new assembly was characterised by using NMR spectroscopy, DOSY, TGA, MS, and molecular modelling techniques. Interestingly, the enlarged cavity size of this new supramolecula

Metal-directed assembly of combinatorial libraries - Principles and establishment of equilibrated libraries with oligopyridine ligands

The cobalt(ii) complexes [Co(bpy)3][PF6]2, [Co(Me2bpy)3][PF6]2 (Me 2bpy = 4,4′-dimethyl-2,2′-bipyridine) and [Co(phen) 3][PF6]2 give paramagnetically shifted 1H NMR spectra which may be fully assigned; the complexes are labile and ligand exchange is complete within mixing time in CD3CN solutions to give libraries of heteroleptic complexes which have been fully characterised by one- and two-dimensional 1H NMR spectroscopy. A library comprising mer and fac isomers of [CoL3]2+ (L = 2,2′-bipyridine-5-carbaldehyde) can be amplified by specific reaction of the fac stereoisomer with a triamine to give a new hexadentate ligand, although other ligand exchange processes compete. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

A self-assembled multiporphyrin cage complex through three different zinc(II) center formation under well-balanced aqueous conditions

Construction of a self-assembled cage complex through three different ZnII centers is achieved using a Zn porphyrin ligand with four 2,2′-bipyridin-5-yl (bpy) groups. The multiporphyrin cage encapsulates guest molecules unsymmetrically by π-π interactions. Well-balanced aqueous conditions, which allow the formation of both tris(bpy) and hydrated bis(bpy) ZnII units, result in the unsymmetrical yet well-defined supramolecular structure. Copyright

HETEROCYCLIC COMPOUND, PHARMACEUTICAL COMPOSITION COMPRISING SAME, PREPARATION METHOD THEREFOR, AND USE THEREOF

The present invention relates to a heterocyclic compound, a pharmaceutical composition comprising same, a preparation method therefor, and a use thereof. Specifically, the compound of the present invention is represented by formula (I), and used for preventing or treating a disease or condition related to RET activity.

Unusual chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage

The chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage was presented. It was shown that i-Pr2Zn do not add to the aldehyde moiety but to the 2-position of the bipyridine to afford possessing a quaternary carbon atom in a yield of 69%. It was found that the i-Pr2Zn does not add to the aldehyde but to the 2-position of the bipyridine ring by destroying the aromaticity of the pyridine ring.