1141-05-5

Usage

Uses

Used in Coordination Chemistry:
1,2-di(2-pyridyl)ethanediol is used as a chelating ligand for the formation of stable coordination complexes with various metal ions. Its application is crucial in coordination chemistry due to its ability to bind metals effectively, facilitating the study and application of metal complexes.
Used in Catalysis:
In the field of catalysis, 1,2-di(2-pyridyl)ethanediol is employed as a ligand in the synthesis of metal complexes that can act as catalysts. The complexes formed with DPED can enhance the efficiency and selectivity of catalytic processes.
Used in Medicinal Chemistry:
1,2-di(2-pyridyl)ethanediol is utilized as a component in the development of metal-based pharmaceuticals. The metal complexes with DPED can possess biological activity, making them potential candidates for drug discovery and medicinal applications.
Used in Material Science:
In material science, 1,2-di(2-pyridyl)ethanediol is used in the creation of metal-organic frameworks (MOFs) and other advanced materials. The metal complexes formed with DPED contribute to the properties of these materials, which can be tailored for specific applications such as sensing, energy storage, or optoelectronics.
These applications underscore the importance of 1,2-di(2-pyridyl)ethanediol as a foundational compound in various scientific and industrial processes, where its unique ability to chelate with metals is harnessed to create functional and innovative materials.

InChI:InChI=1/C12H12N2O2/c15-11(9-5-1-3-7-13-9)12(16)10-6-2-4-8-14-10/h1-8,11-12,15-16H

Upstream product

• 1141-06-6 2-hydroxy-1,2-di-2-pyridylethanone 
• 1121-60-4 pyridine-2-carbaldehyde 
• 67-64-1 acetone 
• 134842-12-9 (E)-1,2-di(pyridin-2-yl)ethene-1,2-diol 
• 492-73-9 2,2'-Pyridil 
• 109-06-8 α-picoline 
• 100-52-7 benzaldehyde 

Downstream Products

• 99310-64-2 hydroxy-(1-oxy-[2]pyridyl)-acetonitrile 
• 24145-28-6 (E)-2-pyridinecarbaldehyde 1-oxide oxime 
• 1121-60-4 pyridine-2-carbaldehyde 

Relevant academic research and scientific papers

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

Bifunctional copper-based photocatalyst for reductive pinacol-type couplings

A bifunctional copper-based photocatalyst has been prepared that employs a pyrazole-pyridine ligand incorporating a sulfonamide moiety that functions as an intramolecular hydrogen-bond donor for a photochemical PCET process. In typical reductive PCET processes, the photocatalyst and H-bond donor must have an appropriate redox potential and pKa, respectively, to promote the PCET. When working in concert in a bifunctional catalyst such as Cu(pypzs)(BINAP)BF4, the pKa of the H-bond donor can have an acidity that is orders of magnitude less and still efficiently promote the PCET process. A reductive pinacol-type coupling can be performed using a base-metal derived photocatalyst to afford valuable diols (24 examples, 46-99% yield), from readily available aldehydes and ketones.

Chemo- and diastereoselectivity in the heterogeneous catalytic hydrogenation of 2,2′-pyridoin and its derivatives

The heterogeneous catalytic hydrogenations of 2,2′-pyridoin and related compounds, such as 2,2′-pyridil and O-acetyl-2,2′-pyridoin, were investigated over noble metal catalysts. The influence of catalytic metals, catalyst supports, solvents, acid additives, prehydrogenation, and hydrogen pressure on the chemo- and diastereoselectivity is discussed in the hydrogenation of 2,2′-pyridoin. Although hydrogenolysis and ring saturation may occur as side reactions, high chemo- (90-100%) and moderate diastereoselectivity values were achieved. Over palladium black in an acetonitrile-water solvent mixture, the hydrogenation resulted in a meso/dl ratio of 72/28, while in the hydrogenation over rhodium on carbon the meso/dl ratio was 29/71. The phenomenon of diastereoselection in the hydrogenation is explained by the stereochemistry of the hydrogen addition, considering the cis-trans isomerization on the catalyst surface, the possible enolization, and the competing C=C and C=O reductions.

Novel Visible-Light-Driven Photocatalyst. Poly(p-phenylene)-Catalyzed Photoreductions of Water, Carbonyl Compounds, and Olefins

The insoluble yellow powder of poly(p-phenylene) (PPP) prepared by nickel-catalyzed polycondensation of the Grignard reagent from 1,4-dibromobenzene shows photocatalytic activity under visible light toward water, carbonyl compounds, and olefins.Water is photoreduced to H2 in the presence of amines as sacrificial electron donors.The H2 evolution is enhanced 3-20 times by noble-metal deposition, in which Ru deposition is the most effective.Apparent quantum yields (Φ(1/2H2)) for Ru-loaded PPP-catalyzed H2 evolution depend on the irradiation wavelength, reaching a maximum value of 0.015 at 405 nm.On the other hand, nonmetallized PPP can more efficiently photocatalyze the reduction of carbonyls and electron-deficient olefins by triethylamine in methanol compared to Ru-loaded PPP, in cases where the reduction potentials of the substrates are more positive than -2.0 V vs Ag/0.01 M AgNO3.The carbonyls are reduced to the corresponding alcohols and/ or pinacols, whereas the reduction of the olefins to the dihydro compounds is accompanied by rapid cis-trans photoisomerization.From the deuterium incorporation experiments for the photocatalyzed reduction of methyl 4-cyanocinnamate, 6j, in methanol-O-d, disproportionation of one-electron-transfer reduction intermediates is suggested to be responsible for the eventual two-electron reductions and the cis-trans-photoisomerization.The physical and spectral properties of PPP's are characterized, and the mechanism is discussed in terms of the energy structure.

REACTIVITY OF HETEROAROMATIC ALDEHYDES WITH LOW VALENT TITANIUM

Behaviour of various aromatic heterocycles under dicarbonylic coupling with low valent titanium was studied.The results showed that the electron donating properties of the ring affect the degree of oxidation of the coupled compound.

A CONVENIENT SYNTHESIS OF SUBSTITUTED PYRIDYLGLYCOLS PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE

2- and 4-Acetylpyridines, and 2- and 4-pyridinealdehydes when allowed to react with two-equiv. of aqueous titanium trichloride add to the carbonyl carbon atom of simple ketones (acetone, cyclopentanone, cyclohexanone) and aldehydes (acetaldehyde, propionaldehyde, benzaldehyde) affording substituted pyridylglycols in very good yields.The present one-pot method has considerable advantage over the existing procedure.The reaction is discussed in terms of a radical mechanism in which the Ti(III) species plays the fundamental role.

REDUCTIVE REACTIONS OF SUBSTITUTED PYRIDINES BY AQUEOUS TITANIUM TRICHLORIDE

Aqueous titanium trichloride reductively removes cyano and halo groups from the correspondingly substituted pyridines by a two electron-transfer process and promotes reduction of pyridyl-ketones and aldehydes to glycols by one electron-transfer process under very simple experimental conditions.