1539-48-6

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Pyridinedicarbonitrile, 2,4,6-trimethylis used as a precursor in the synthesis of various pharmaceuticals for its versatile chemical properties. It plays a crucial role in the development of new drugs and medicines.
Used in Dye Industry:
In the dye industry, 3,5-Pyridinedicarbonitrile, 2,4,6-trimethylis used as a starting material for the production of various dyes. Its unique chemical structure allows for the creation of a wide range of colors and hues.
Used in Agrochemical Industry:
3,5-Pyridinedicarbonitrile, 2,4,6-trimethylis also utilized in the agrochemical industry as a precursor for the synthesis of various agrochemicals. Its application contributes to the development of effective pesticides and other agricultural chemicals.
It is important to handle 3,5-Pyridinedicarbonitrile, 2,4,6-trimethylwith care, as it can be toxic if ingested or inhaled and can cause irritation to the skin and eyes upon contact. Proper safety measures should be taken during its use and storage to minimize potential health risks.

Upstream product

• 3274-37-1 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarbonitrile 
• 1118-61-2 3-Aminocrotononitrile 
• 75-07-0 acetaldehyde 
• 23079-73-4 3-bromo-2,4,6-trimethylpyridine 
• 544-92-3 copper(I) cyanide 
• 29976-56-5 2,4,6-trimethyl-3,5-dibromopyridine 
• 75-05-8 acetonitrile 
• 108-75-8 2,4,6-trimethyl-pyridine 

Downstream Products

• 1195-58-0 pyridine-3,5-dicarbonitrile 

Relevant academic research and scientific papers

Self-assembled columnar mesophase from a new disclike polar mesogen based on a 3,5-dicyano-2,4,6-tristyrylpyridine core

We report on the design and synthesis of a new disc-like Liquid crystal based on a 3,5-dicyano-2,4,6-tristyrylpyridine core. The mesogenic behavior was investigated by differential scanning calorimetry, polarized-light optical microscopy, and X-ray diffra

Electrosynthesis of pyridines from 'only acetonitrile'

2,4,6-Trimethylpyridine-3,5-dicarbonitrile has been obtained as the main product after the electrolysis of acetonitrile in the presence of tetrabutylammonium bisulfate as supporting electrolyte using a divided cell with a medium porosity diaphragm. 2,6-Dimethylpyridine-3,5-dicarbonitrile and 2,6-dimethylpyridine-3,4,5-tricarbonitrile have also been obtained in minor quantity. This process, which takes place with participation of both electrodes, is an example of a paired electrosynthesis.

Conformational control and photoenolization of pyridine-3-carboxaldehydes in the solid state: Stabilization of photoenols via hydrogen bonding and electronic control

We have investigated the solid-state photobehavior of a broad set of pyridine-3-carboxaldehydes 1-5. The introduction of a heteroatom into mesitaldehydes as in aldehydes 1 raises the question of conformational preference in the solid state. The preferred conformations have been unequivocally established from X-ray crystal structure analyses of two of the aldehydes, 1c and 2c; it is shown that intramolecular hydrogen bonding could be utilized to achieve conformational control. In contrast to mesitaldehydes, which undergo efficient photocyclization to benzocyclobutenols in the solid state, the heteroatom analogues 1b and 1c exhibit a perceptible color change (from colorless to pale yellow for 1b and yellow-orange for 1c) upon UV irradiation; the color attributed to (E)-enols is persistent for several hours. Continued irradiation leads to an intractable polymeric material. The AM1 calculations, which have been reliably applied to the thermal cyclization of xylylenols to benzocyclobutenols, reveal that the (E)-enols of 1 are more stable than those of the mesitaldehydes relative to their corresponding benzocyclobutenols. The stabilization is interpreted as arising from the possibility of engaging the heteroatom in resonance delocalization. That the contribution from such a role of the nitrogen atom is so pronounced is elegantly demonstrated by forming the fluoroborate salts; 1a-HBF4 and 1b-HBF4 readily exhibit highly red-shifted absorption upon exposure to UV radiation as a result of stabilization of the photoenols. Notably, such a remarkable stabilization via electronic control of the photoenols is unprecedented. All of the 2-methoxy- and 2-chloro-substituted aldehydes 2-5 exhibit photochromism. Ab initio calculations show that the methoxy group in aldehydes 2 and 3 stabilizes the (E)-enols via O-H...O hydrogen bonding as compared to those of 1 by 5-6 kcal/mol relative to their corresponding benzocyclobutenols. Thus, the presence of methoxy and halo groups at position 2 serves not only to direct the formyl oxygen toward the methyl group for H-abstraction but also to stabilize the (E)-enols.

Synthesis of 2,6-dimethyl-4-substituted pyridine-3,5-dicarbonitriles from β-aminoacrylonitriles

β-Aminoacrylonitrile reacts with aldehydes or cinnamaldehyde in the presence of HCl to give 2,6-dimethyl-4-substituted pyridine-3,5-dicarbo/nitrites 2a-c. 2a-b on condensation with DMF/DMA afford 8a-b. Reaction of 2b with 4-N,N-dimethylaminobenzaldehyde yields 8c. The structures of the newly synthesized compounds have been elucidated by elemental analyses and spectral data.