4913-57-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2,6-Dimethyl-4-nitropyridine is utilized as a key intermediate in the synthesis of various organic molecules, particularly in the production of pharmaceuticals. Its role in the formation of carbon-carbon and carbon-heteroatom bonds is crucial for creating complex molecular structures that can be used in the development of new drugs.
Used in Agrochemical Production:
In the agrochemical industry, 2,6-Dimethyl-4-nitropyridine serves as a vital component in the synthesis of various agrochemicals. Its ability to form stable bonds with other molecules makes it suitable for creating compounds that can be used in pesticides, herbicides, and other agricultural products to enhance crop protection and yield.
Used as a Reagent in Chemical Reactions:
2,6-Dimethyl-4-nitropyridine is also employed as a reagent in chemical reactions, where its capacity to form stable bonds is leveraged to facilitate the synthesis of a wide array of organic compounds. Its use in these reactions contributes to the advancement of organic chemistry and the creation of new materials and substances with various applications.

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 4808-64-4 4-nitro-2,6-lutidine-1-oxide 
• 325142-95-8 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1073-23-0 2,6-lutidine N-oxide 

Downstream Products

• 1250445-93-2 4-nitro-2,6-diacetylpyridine bis(2,4,6-trimethylphenylimine) 
• 63897-10-9 4-nitro-pyridine-2,6-dicarboxylic acid 
• 3512-80-9 4-amino-2,6-lutidine 
• 107774-56-1 3,5-dimethyl-1-(phenylsulphonyl)benzene 
• 358621-46-2 2,6-bis(bromomethyl)-4-nitropyridine 

Relevant academic research and scientific papers

Electronic influence of substitution on the pyridine ring within NNN pincer-type molecules

Pincer molecules are of increasing interest due to the modular nature of modification and range of reactivity observed when coordinated to metal ions. A subset within the family of pincer molecules use a pyridine group to bridge the outer two arms as well as provide a N-donor atom for metal binding. While the arm appendages have been studied extensively, little research has been conducted on the electronic effects of the central, substituted pyridine systems. Therefore, a series of NNN pincer-type ligands with substitution on the 4-position of the pyridine ring with -OH, -OBn, -H, -Cl, and -NO2 functional groups were synthesized and characterized through NMR spectroscopy and ESI-HRMS. Each pincer was metalated with Cu(ii) salts and evaluated through X-ray diffraction analysis, cyclic voltammetry, and density functional theory analysis. The results indicate that the relatively unstudied -OBn group demonstrates both electron-withdrawing (XRD bond lengths) and electron-donating (NMR spectroscopy) properties. The -NO2 pincer ligand shows a redox event within experimental windows evaluated, in contrast to the other congeners studied. In addition, electron-donating groups increase the electron density around the Cu(ii) center based on DFT studies and cyclic voltammetry. These findings can be applied to other pyridine-based pincer systems when considering ligand design and warrants future characterization of 4-position substituted pyridines.

Synthesis of 12-Membered Tetra-aza Macrocyclic Pyridinophanes Bearing Electron-Withdrawing Groups

The number of substituted pyridine pyridinophanes found in the literature is limited due to challenges associated with 12-membered macrocycle and modified pyridine synthesis. Most notably, the electrophilic character at the 4-position of pyridine in pyridinophanes presents a unique challenge for introducing electrophilic chemical groups. Likewise, of the few reported, most substituted pyridine pyridinophanes in the literature are limited to electron-donating functionalities. Herein, new synthetic strategies for four new macrocycles bearing the electron-withdrawing groups CN, Cl, NO2, and CF3 are introduced. Potentiometric titrations were used to determine the protonation constants of the new pyridinophanes. Further, the influence of such modifications on the chemical behavior is predicted by comparing the potentiometric results to previously reported systems. X-ray diffraction analysis of the 4-Cl substituted species and its Cu(II) complex are also described to demonstrate the metal binding nature of these ligands. DFT analysis is used to support the experimental findings through energy calculations and ESP maps. These new molecules serve as a foundation to access a range of new pyridinophane small molecules and applications in future work.

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

Generic tags for Mn(II) and Gd(III) spin labels for distance measurements in proteins

High-affinity chelating tags for Gd(iii) and Mn(ii) ions that provide valuable high-resolution distance restraints for biomolecules were used as spin labels for double electron-electron resonance (DEER) measurements. The availability of a generic tag that can bind both metal ions and provide a narrow and predictable distance distribution for both ions is attractive owing to their different EPR-related characteristics. Herein we introduced two paramagnetic tags, 4PSPyMTA and 4PSPyNPDA, which are conjugated to cysteine residues through a stable thioether bond, forming a short and, depending on the metal ion coordination mode, a rigid tether with the protein. These tags exhibit high affinity for both Mn(ii) and Gd(iii) ions. The DEER performance of the 4PSPyMTA and 4PSPyNPDA tags, in complex with Gd(iii) or Mn(ii), was evaluated for three double cysteine mutants of ubiquitin, and the Gd(iii)-Gd(iii) and Mn(ii)-Mn(ii) distance distributions they generated were compared. All three Gd(iii) complexes of the ubiquitin-PyMTA and ubiquitin-PyNPDA conjugates produced similar and expected distance distributions. In contrast, significant variations in the maxima and widths of the distance distributions were observed for the Mn(ii) analogs. Furthermore, whereas PyNPDA-Gd(iii) and PyNPDA-Mn(ii) delivered similar distance distributions, appreciable differences were observed for two mutants with PyMTA, with the Mn(ii) analog exhibiting a broader distance distribution and shorter distances. ELDOR (electron-electron double resonance)-detected NMR measurements revealed some distribution in the Mn(ii) coordination environment for the protein conjugates of both tags but not for the free tags. The broader distance distributions generated by 4PSPyMTA-Mn(ii), as compared with Gd(iii), were attributed to the distributed location of the Mn(ii) ion within the PyMTA chelate owing to its smaller size and lower coordination number that leave the pyridine nitrogen uncoordinated. Accordingly, in terms of distance resolution, 4PSPyNPDA can serve as an effective generic tag for Gd(iii) and Mn(ii), whereas 4PSPyMTA is efficient for Gd(iii) only. This comparison between Gd(iii) and Mn(ii) suggests that PyMTA model compounds may not predict sufficiently well the performance of PyMTA-Mn(ii) as a tag for high-resolution distance measurements in proteins because the protein environment can influence its coordination mode.

Novel late transition metal catalysts based on iron: Synthesis, structures and ethylene polymerization

In this article we reported synthesis, characterization and ethylene polymerization behavior of two new late transition metal 2,6-bis(imino)pyridine catalysts based on iron(II) possessing different substituents of NO2 (catalyst b) and OMe (catalyst c) at the para position of the pyridine ring. Theoretical study exhibited more positive charge on the central metal of the catalyst b, leading to higher activity offset by lower thermal stability and life time.