581-47-5

Usage

Uses

Used in Chemical Synthesis:
2,4'-DIPYRIDYL is used as a key component in the preparation of Iridium Heterocyclic complexes. These complexes are of significant interest in various fields, including catalysis, photovoltaics, and medicinal chemistry, due to their unique electronic and structural properties.
Used in Coordination Chemistry:
In coordination chemistry, 2,4'-DIPYRIDYL serves as a versatile ligand for the formation of metal complexes. Its ability to chelate metal ions through its nitrogen atoms makes it a valuable building block for creating stable and functional coordination compounds.
Used in Analytical Chemistry:
2,4'-DIPYRIDYL is employed as a reagent in analytical chemistry for the detection and quantification of various metal ions. Its selective binding properties allow for the development of sensitive and selective assays for metal ion analysis.
Used in Pharmaceutical Industry:
2,4'-DIPYRIDYL is used as a starting material or intermediate in the synthesis of certain pharmaceutical compounds. Its unique chemical structure can be exploited to design and develop new drugs with potential therapeutic applications.
Used in Material Science:
In material science, 2,4'-DIPYRIDYL can be utilized in the development of novel materials with specific properties, such as conductivity, magnetism, or luminescence. Its ability to form complexes with various metal ions can lead to the creation of advanced materials with tailored properties for specific applications.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 2199, 1992 DOI: 10.1016/0040-4039(92)88176-6Synthesis, p. 564, 1986 DOI: 10.1055/s-1986-31705

Upstream product

• 110-86-1 pyridine 
• 114998-58-2 dodecahydro-[2,4']bipyridinyl 
• 3731-53-1 4-(aminomethyl)pyridine 
• 115486-02-7 [2,4']bipyridyl-2',6'-dicarboxylic acid 
• 4433-02-7 [2,4']bipyridyl-3,3'-dicarboxylic acid 
• 93845-11-5 C₁₉H₁₄N₂O₂ 
• 93845-12-6 C₁₉H₁₄N₂O₂ 
• 626-60-8 3-Chloropyridine 
• 109-09-1 2-chloropyridine 
• 93830-58-1 diethyl (pyridin-4-yl)borane 
• 109-04-6 2-bromo-pyridine 
• 626-61-9 4-Chloropyridine 
• 17997-47-6 2-tri-n-butylstannylpyridine 
• 1120-87-2 4-bromopyridin 

Downstream Products

• 110462-45-8 iodure de 1-methyl-4-(2-pyridyl)pyridinium 
• 63095-06-7 1,1'-dimethyl-[2,4']bipyridyldiium; diiodide 
• 143702-84-5 Phenyl-(2-pyridin-2-yl-4a,5,10,11-tetraaza-benzo[b]fluoren-7-yl)-methanone 
• 143924-45-2 1',2',3',4',5',6'-hexahydro-2'H-[2,4'-bipyridine] dihydrochloride 
• 869103-18-4 [Cu(2,4'-bipyridine)(phenylmalonato)(H₂O)](n) 
• 1151768-41-0 3-[3,6-dihydroxy-2-(4-(pyridin-2-yl)pyridinium-1-yl)phenyl]-2-oxo-2H-chromen-4-olate 
• 1329663-93-5 C₃₈H₂₆N₂ 
• 1431535-97-5 [zinc(2,4'-bipyridine)(H₂O)((+)-N-tosyl-L-glutamate)] 

Relevant academic research and scientific papers

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.

C2-Selective silylation of pyridines by a rhodium-aluminum complex

We have developed a C2-selective mono-silylation of a variety of pyridines using a Rh-Al complex. Both the site- and mono-selectivity are controlledviathe pyridine coordination to the Lewis-acidic Al center prior to the activation of the pyridine C(2)-H bond at the proximal Rh center. A reaction mechanism is proposed based on several mechanistic studies, including the isolation of a (2-pyridyl)silylrhodium intermediate.

Copper-catalyzed cross-coupling of aryl-, primary alkyl-, and secondary alkylboranes with heteroaryl bromides

A method for the Cu-catalyzed cross-coupling of both aryl and alkylboranes with aryl bromides is described. The method employs an inexpensive Cu-catalyst and functions for a variety of heterocyclic as well as electron deficient aryl bromides. In addition, aryl iodides of varying substitution patterns and electronic properties work well.

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.

Au-complex containing phosphino and imidazolyl moieties as a bi-functional catalyst for one-pot synthesis of pyridine derivatives

The complex of Au-L1 containing imidazolyl ring and the phosphine-ligated-Au moiety was synthesized and applied as the efficient bi-functional catalyst for the one-pot sequential condensation/annulation reaction for the synthesis of pyridine derivatives. It was found that, as for Au-L1, the involved imidazolyl group acted as a Lewis base to catalyze the condensation of carbonyl compounds with propargylamine to form the imino intermediate, and the involved Au+-complex species with alkynophilicity corresponded to the subsequent activation of imino-tailed alkynyl to afford dehydropyridine intermediate. The latter proceeded auto-oxidation reaction to afford the pyridine derivatives. The observed sequential catalysis over Au-L1 proved more efficient than that over the mechanical mixtures of the Au-complex (Au-L2) and N-methylimidazole, because the free N-methylimidazole as an N-containing donor competed with the alkyne substrate to coordinate to Au-center. Moreover, Au-L1 exhibited good generality to a wide range of the substrates for the synthesis of 2,3-fused pyridine derivatives and 2-aryl(heteroaryl)-substituted pyridines.

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates

A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib. A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.

Aerobic C-N bond activation: A simple strategy to construct pyridines and quinolines

Inspired by the autoxidation processes, a dioxygen induced C-N bond activation of primary alkyl amines was demonstrated toward the synthesis of pyridines and quinolines. The transition-metal free conditions with O2 as the sole oxidant make this transformation very attractive. Notably, the substrate applicability of different kinds of ketones is greatly broadened for this transformation.

Arylation of 2-substituted pyridines via Pd-catalyzed decarboxylative cross-coupling reactions of 2-picolinic acid

The novel palladium-catalyzed decarboxylative cross-coupling reactions of 2-picolinic acid with aryl and heteroaryl bromides including benzenes, naphthalenes, pyridines and quinolines for C-C bond formation have been successfully achieved. This journal is

Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes

An amino-linked nitrogen heterocyclic carbene (amino-NHC), 1-tBu, has been shown to mediate carbon-carbon coupling through the direct C-H functionalization of benzene and pyridine in the absence of a metal catalyst. Using EPR, the first spectroscopic evidence corroborating the single electron transfer mechanism for the metal-free carbon-carbon coupling manifold, as reported by others, is introduced.