22346-73-2

Usage

Uses

Used in Organic Synthesis:
3-Picolinaldehyde-N-oxide is used as a reagent in organic synthesis for the preparation of various organic compounds due to its ability to chelate metal ions, which can facilitate certain chemical reactions.
Used in Biochemical Research:
In biochemical research, 3-Picolinaldehyde-N-oxide is used as a ligand in coordination chemistry, which aids in the study of metal ion interactions and their biological implications.
Used in Pharmaceutical Development:
3-Picolinaldehyde-N-oxide is utilized in the development of pharmaceuticals and nutraceuticals due to its antioxidant and free radical scavenging properties, which can contribute to health and disease prevention.
Used in Materials Science:
In materials science, 3-Picolinaldehyde-N-oxide has potential applications in the creation of new materials or the modification of existing ones, taking advantage of its chelating and antioxidant characteristics.
Used as a Fluorescent Probe in Biological Systems:
3-Picolinaldehyde-N-oxide is also studied for its potential as a fluorescent probe for detecting metal ions in biological systems, which can be instrumental in understanding metal ion distribution and function within living organisms.

Upstream product

• 109163-00-0 1,2-bis-(1-oxy-[3]pyridyl)-ethane-1,2-diol 
• 76037-08-6 3-(dihydroxymethyl)pyridine-N-oxide 
• 41668-21-7 1,2-di-[3]pyridyl-ethane-1,2-diol 
• 114951-44-9 3-pyridine carbaldehyde diacetate 
• 114951-35-8 3-pyridinecarbaldehyde diacetate 1-oxide 

Downstream Products

• 120614-51-9 3-pyridinecarboxaldehyde N-oxide phenylhydrazone 

Relevant academic research and scientific papers

Chemoselective N-oxidation of picolinaldehydes with dimethyldioxirane

The N-oxidation of picolinaldehydes with dimethyldioxirane proceeds with remarkable selectivity. Especially the N-oxides of 3- and of 4- picolinaldehyde are isolated in high yields. The aldehyde-hydrate 3- dihydoxymethylpyridin-N-oxide was fully characterized.

The Mechanism of the Reaction of Nicotinic Acid 1-Oxide with Acetic Anhydride

In order to elucidate the mechanism of the 2-acetylation in the reaction of nicotinic acid 1-oxide (2a) with boiling acetic anhydride, thermal reactions and reactions with hot acetic anhydride have been explored with 3-X-pyridine 1-oxides (2).The former reactions of 2d (X = CONHAc), 2f (X = CONMeAc), 2h (X = CH2OAc) and 2j result in recovery or decomposition.The latter reactions of 2c (X = CONH2), 2d, 2e (X = CONHMe), 2h and 2j bring about mainly deoxygenative α-acetoxylation, no 2-acetylation being noticed.However, the reaction of 2f with acetic anhydride affords 6,7-dihydro-6-methyl-7-methylene-5H-pyrrolopyridin-5-one 1-oxide (7) as an initial product, which further undergoes deoxygenative β-acetoxylation to give 7-acetoxy-7-acetoxymethyl-6,7-dihydro-6-methyl-5H-pyrrolopyridin-5-one (8) and 7-acetoxymethylene-6,7-dihydro-6-methyl-5H-pyrrolopyridin-5-one (9).On the basis of the results we propose a new electrophilic pathway for the 2-acetylation of 2a and 2f.Keywords - pyridine 1-oxide 3-substituted; nicotinic acid 1-oxide; nicotinamide 1-oxide N-acetyl-N-methyl; pyrrolopyridine; 2-acetylation; pyridone formation