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Usage

Uses

Used in Pharmaceutical Industry:
2,6-DIMETHYL-3-NITROPYRIDINE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2,6-DIMETHYL-3-NITROPYRIDINE serves as an intermediate in the production of agrochemicals. Its application aids in the creation of compounds that can be used in pest control and crop protection, thereby supporting agricultural productivity.
Used as a Reagent in Organic Chemistry:
2,6-DIMETHYL-3-NITROPYRIDINE is utilized as a reagent in a variety of organic chemistry reactions. Its presence can facilitate or enhance specific chemical processes, making it a valuable tool for researchers and chemists in the field of organic synthesis.

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 97055-58-8 1,4-Dimethyl-3,5-dinitro-2-pyridone 
• 67-64-1 acetone 
• 97055-50-0 1,6-Dimethyl-3,5-dinitro-2-pyridone 
• 5860-71-9 2,6-dimethylpyridine-3-carboxylic acid 

Downstream Products

• 33883-98-6 6-methyl-3-nitro-2-trans-styryl-pyridine 
• 142078-39-5 3-nitro-2,6-distyrylpyridine 
• 24194-98-7 2-methyl-3-nitropyridine-6-carboxylic acid 
• 42753-74-2 sulfanilic acid-(2,6-dimethyl-[3]pyridylamide) 
• 855932-44-4 N-acetyl-sulfanilic acid-(2,6-dimethyl-[3]pyridylamide) 
• 854018-76-1 2,5-dimethyl-1H-pyrrolo[3,2-b]pyridine 
• 860362-36-3 5-methyl-2-phenyl-1H-pyrrolo[3,2-b]pyridine 
• 65156-92-5 2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine 

Relevant academic research and scientific papers

Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate

A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.

Nucleophilic reaction upon electron-deficient pyridone derivatives. XIII. Regioselective synthesis of 2-substituted 3-nitropyridines by one-pot reaction of either 4- or 6-substituted 1-methyl-3,5-dinitro-2-pyridones with ketones and ammonia

A one-pot synthesis of 2-substituted 3- nitropyridines was developed by a ring transformation of 6- or 4-substituted 1-methyl-3,5-dinitro-2-pyridones (2 or 3) with ammonia and enamines derived from ketones. Some intermediates having a 2,6-diazabicyclo[3.3.1]nonane skeleton were isolated from reactions of 3. The ring transformation proceeds via an addition-addition-elimination-elimination mechanism. Few competitive isomeric by-products, 4-substituted 3-nitropyridines and 4-nitroanilines, were formed. All the 2 substrates showed good reactivity, but the 3 substrates having electron-withdrawing substituents were less reactive and selective. 1,4,6-Trimethyl-3,5-dinitro-2-pyridone did not give any products. The selectivity is interpreted in terms of differences of thermodynamic (main selection rule B) and kinetic stability (minor selection rule A) between the possible bicyclic intermediates which are expected to be formed via the mechanism.

Nitration of Aromatic and Heteroaromatic Compounds by Dinitrogen Pentaoxide

Nitration of benzene and monosubstituted benzenes in liquid SO2 by dinitrogen pentaoxide at - 11 deg C gave the corresponding nitroarenes with substitution patterns similar to those obtained by nitrations with HNO3-H2SO4.For acetophenone an o/m ratio of 0.94 was obtained.The yields were dependent on the substituents.With a 1:1 ratio of arene: N2O5 the yields varied from 73percent for toluene to 0.4percent for nitrobenzene as substrates.From competition experiments and the nitration of bibenzyl it was concluded that the reaction was faster than the macroscopic rate of mixing.The qualitative order of reactivity for PhX was X = OCH3>CH3>H>Cl>CH3CO>NO2.Nitration with N2O5 in liquid CO2 gave similar results.Nitration of pyrimidine, pyrrole, imidazole and indole with N2O5-SO2 gave no nitrated products.With thiophene, 2- (34percent) and 3-nitrothiophene (5percent) together with 2,4-(16percent) and 2,5-dinitrothiophene (8percent) were obtained.With pyridine, mono- and di-methylpyridines, quinoline, isoquinoline and 4-phenylpyridine nitration of the pyridine ring was obtained.The yields varied from ca. 70percent to 16percent, except for 3,5-, 2,5- and 2,6-dimethylpyridine for which only traces of nitro-dimethylpyridines were obtained.The reaction with the pyridines appears to be intramolecular both in the SO2 phase and in the water phase used for quenching the reaction.The reaction was proposed to proceed by a complex formed in liquid SO2:

REGIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 3-NITROPYRIDINES BY ONE-POT REACTION OF EITHER 4- OR 6-SUBSTITUTED 1-METHYL-3,5-DINITRO-2-PYRIDONES WITH KETONES AND AMMONIA

Regioselective synthesis of 2-substituted 3-nitropyridines was achieved by one-pot reaction of either 4- or 6-substituted 1-methyl-3,5-dinitro-2-pyridones with ketones in the presence of ammonia.The selectivity is interpreted in terms of steric factor of substituent on the pyridone.

OXIDATIVE DEMETHYLATION OF SOME METHYLNITROPYRIDINE 1-OXIDES

3-Nitropyridine 1-oxide and 5-methyl-3-nitropyridine 1-oxide are produced readily by oxidative demethylation using SeO2 of 2-methyl- and 2,5-dimethyl-3-nitropyridine 1-oxides.