824-40-8

Basic information

• Product Name: PICOLINIC ACID N-OXIDE
• Synonyms: 1-Oxopicolinic acid;2-Carboxylicacid-pyridine-1-oxide;2-Carboxypyridine N-oxide;Picolinic acid N-oxide 97%;picolinicacid-oxide;2-PICOLINIC ACID-N-OXIDE;PYRIDINE-2-CARBOXYLIC ACID 1-OXIDE;RARECHEM AL BO 1646
• CAS NO: 824-40-8
• Molecular Formula: C₆H₅NO₃
• Molecular Weight: 139.11
• EINECS: 212-528-0
• Product Categories: Heterocyclic Building Blocks;pharmacetical;Heterocyclic Compounds;C6;Heterocyclic Building Blocks;Pyridines;Building Blocks;Chemical Synthesis
• Mol File: 824-40-8.mol

Chemical Properties

• Melting Point: 162 °C (dec.)(lit.)
• Boiling Point: 255.04°C (rough estimate)
• Flash Point: 237.4°C
• Appearance: White to beige/Crystals or Crystalline Powder
• Density: 1.4429 (rough estimate)
• Vapor Pressure: 1.34E-09mmHg at 25°C
• Refractive Index: 1.5423 (estimate)
• PKA: 1.57±0.50(Predicted)
• CAS DataBase Reference: PICOLINIC ACID N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PICOLINIC ACID N-OXIDE(824-40-8)
• EPA Substance Registry System: PICOLINIC ACID N-OXIDE(824-40-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 824-40-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H5NO3/c8-6(9)5-3-1-2-4-7(5)10/h1-4H,(H,8,9)/p-1

Upstream product

• 931-19-1 2-methylpyridine N-oxide 
• 98-98-6 2-Picolinic acid 
• 1452-77-3 pyridine-2-carboxylic acid amide 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 2524-52-9 ethyl-2-picolinate 
• 75003-55-3 3-Phenyl-5-pyridin-2-yl-2-thioxo-thiazolidin-4-one 
• 1121-60-4 pyridine-2-carbaldehyde 
• 3243-95-6 3-Methoxalyl-4-oxo-4H-chinolizin-1,2-dicarbonsaeure-dimethylester 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 1008-89-5 2-phenylpyridine 
• 109-06-8 α-picoline 
• 5957-90-4 4-(2-pyridinyl)anisole 
• 4467-06-5 2-(4-methylphenyl)pyridine 

Downstream Products

• 38195-81-2 1-oxy-pyridine-2-carboxylic acid methyl ester 
• 14933-78-9 2-carboxy-4-nitropyridine-1-oxide 
• 694-59-7 pyridine N-oxide 
• 93953-41-4 2-(2-methoxyphenyl)pyridine N-oxide 
• 36710-80-2 2-(4-methoxyphenyl)pyridine N-oxide  
• 84794-09-2 2-(p-nitrophenyl)pyridine N-oxide 
• 119345-59-4 2,6-bis(phenylselenenyl)pyridine 
• 1613316-56-5 2-(4-chlorophenyl)-pyridine N-oxide 
• 33421-24-8 2-(4-methylphenyl)pyridine N-oxide  
• 1131-33-5 2-phenylpyridin N-oxide 

Relevant articles and documents

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Recyclable anhydride catalyst for H2O2 oxidation:: N -oxidation of pyridine derivatives

The catalytic efficiency and recyclability of poly(maleic anhydride-alt-1-octadecene) (Od-MA) and poly(maleic anhydride-alt-1-isobutylene) (Bu-MA) were evaluated for use in the development of a metal-free, reusable catalyst for the oxidation of pyridines to pyridine N-oxides in the presence of H2O2. The Od-MA catalyst was easily recovered via filtration with recovery yields exceeding 99.8%. The catalyst retained its activity after multiple uses and did not require any treatment for reuse. The Od-MA and H2O2 catalytic system described herein is eco-friendly, operationally simple, and cost-effective; thus, it is industrially applicable. Od-MA and H2O2 could potentially be used in place of percarboxylic acid as an oxidant in a wide range of oxidation reactions.

ANTIBACTERIAL THERAPEUTICS AND PROPHYLACTICS

The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.

Catalyst-free and selective oxidation of pyridine derivatives and tertiary amines to corresponding N-oxides with 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane

The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields. Graphical abstract: The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields.

Co(ii), a catalyst for selective conversion of phenyl rings to carboxylic acid groups

An inexpensive protocol for the conversion of -C6H4R into -COOH groups using Co(ii)-Oxone mixture as the catalytic system is described. A series of substrates containing substituted and non-substituted phenyl groups could be selectively converted into carboxylic acids. Initial mechanistic data have been provided.

Copper powder-catalyzed N-arylation of imidazoles in water using 2-(hydrazinecarbonyl)pyridine N-oxides as the new ligands

2-(2-Hydrazinecarbonyl)pyridine N-oxides, which were derived from pyrrole-2-carbohydrazides and pyridine N-oxides, were synthesized and utilized as the ligands for copper powder-catalyzed N-arylation of imidazoles with aryl halides in water. Imidazoles could be arylated smoothly with various aryl halides to provide the title products in preferable yields without the need of an inert atmosphere.

Structural designs and property characterizations for second-harmonic generation materials

Second-harmonic generation (SHG) materials only exist in solids that have no inversion center space groups, and they are constructed by the building blocks or chromophores of noncentrosymmetricity (NCS). In this chapter, we employed one or multiple chromophores that result from the coordination structure distortions of a d0 cation, polar displacement of d 10 cation center, a stereochemically active lone pair (SCALP) of cations, and asymmetrical delocalization π-charge systems, as building blocks to obtain some new compounds with NCS space group. The single-crystal structures were characterized, and physical properties, in particular SHG responses, were measured for these compounds. The electronic structures and density of states were calculated by DFT method, and the SHG properties are simulated to gain an insight into the relations between structure and NLO properties for the materials. The electronic origination of large SHG responses was assigned in terms of the calculated results.

COMPOSITION FOR OXIDATION OF ORGANIC SUBSTRATES

The invention relates to a composition comprising a soluble source of manganese, a ligand, a base, hydrogen peroxide and a ketone or an aldehyde, wherein the ligand is a pyridine heterocycle containing carboxylic acid or a precursor thereof, wherein the nitrogen atom of the pyridine ring is capable of coordinating to the carboxylate bonded manganese center, wherein the 2-position relative to the nitrogen atom is part of the N(pyridine)-Mn-O(carboxylate) containing chelate ring and the second 2-position relative to the nitrogen atom in the ring is not a carboxylic acid group. Furthermore, the invention relates to a process for oxidation of an organic substrate using the composition of the invention.

Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst

Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.

Influence of a reaction medium on the oxidation of aromatic nitrogen-containing compounds by peroxyacids

The influence of different solvents on the oxidation reaction rate of pyridine (Py), quinoline (QN), acridine (AN), α-oxyquinoline (OQN) and a-picolinic acid (APA) by peroxydecanoic acid (PDA) was studied. It was found that the oxidation rate grows in the series Py eq) and its decomposition constant (k2) in acetone and benzene were calculated. It was shown that the nature of the solvent influences the numerical values of both Kp and k2. It was established that introduction of acetic acid (which is able to form compounds with Py) into the reaction medium slows the rate of the oxidation process drastically. Correlation equations linking the polarity, polarizability, electrophilicity, and basicity of solvents with the constant of the PDA oxidation reaction rate for Py were found. It was concluded that the basicity and polarity of the solvent have a decisive influence on the oxidation reaction rate, while the polarizability and electrophilicity of the reaction medium do not influence the oxidation reaction rate. Pleiades Publishing, Ltd., 2011.