1124-33-0

Basic information

• Product Name: 4-Nitropyridine N-oxide
• Synonyms: AKOS 93467;4-NITROPYRIDINE 1-OXIDE;4-NITROPYRIDINE N-OXIDE;4-NITRO-N-OXOPYRIDINE;4-nitro-pyridin1-oxide;4-Nitropyridine oxide;ai3-25256;Avitrol 100
• CAS NO: 1124-33-0
• Molecular Formula: C₅H₄N₂O₃
• Molecular Weight: 140.1
• EINECS: 214-395-4
• Product Categories: Pyridines;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine;Pyridines derivates;C5;Heterocyclic Building Blocks
• Mol File: 1124-33-0.mol

Chemical Properties

• Melting Point: 159-162 °C(lit.)
• Boiling Point: 256.56°C (rough estimate)
• Flash Point: 194 °C
• Appearance: Yellow to brown/Crystals or Powder
• Density: 1.5657 (rough estimate)
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: -1.37±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 124331
• CAS DataBase Reference: 4-Nitropyridine N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitropyridine N-oxide(1124-33-0)
• EPA Substance Registry System: 4-Nitropyridine N-oxide(1124-33-0)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38-40-23/24/25
• Safety Statements: 26-45-37/39-28A-36-22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: UT6380000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1124-33-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitropyridine N-oxide is used as an inhibitor for Na,K-ATPase activity, which plays a crucial role in maintaining the electrochemical gradient across cell membranes. Its ability to inhibit this activity makes it a potential candidate for the development of drugs targeting conditions related to ion transport and membrane potential regulation.
Used in Agricultural and Environmental Applications:
As a quorum sensing inhibitor, 4-Nitropyridine N-oxide can be employed in the development of anti-microbial agents to control bacterial populations, particularly in the context of pathogenic bacteria that rely on quorum sensing for virulence and biofilm formation. This application can be beneficial in agriculture for crop protection and in environmental management for controlling bacterial growth in water systems.
Used in Chemical Synthesis:
4-Nitropyridine N-oxide serves as a key intermediate in the preparation of several 4-substituted pyridine-N-oxides and pyridines. These synthesized compounds can be utilized in various chemical and pharmaceutical applications, including the development of new drugs, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties and potential applications, 4-Nitropyridine N-oxide is a valuable compound for research and development purposes. It can be used in the study of ion transport, membrane potential regulation, and quorum sensing mechanisms, as well as in the development of new synthetic methods and applications for pyridine-N-oxides and related compounds.

Preparation

pyridine is reluctant to undergo electrophilic nitration, pyridine-N-oxide is activated to electrophilic attack and nitration gives 4-nitropyridine-N-oxidel.

Air & Water Reactions

May be deliquescent.

Reactivity Profile

Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction.

Health Hazard

High toxicity via oral exposure.

Fire Hazard

When heated to decomposition, 4-Nitropyridine N-oxide emits very toxic fumes of nitrogen oxides. Avoid decomposing heat.

Safety Profile

Poison by ingestion and skincontact. Questionable carcinogen with experimentaltumorigenic data. Mutation data reported. Mixtures withdiethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylateexplode when heated above 130°C. When heated todecompositio

InChI:InChI=1/C5H4N2O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4H

Upstream product

• 694-59-7 pyridine N-oxide 
• 1122-61-8 4-nitropyridine 
• 355-43-1 n-perfluorohexyl iodide 
• 120309-62-8 C₅₆H₉₈O₃₅*C₅H₄N₂O₃ 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 933761-82-1 (H₂O)5 chromium(III)(4-NO₂-pyridine-N-oxide) 
• 16527-88-1 Pyridine 1-oxide hydrochloride 

Downstream Products

• 14248-50-1 4-bromopyridine-1-oxide 
• 2632-99-7 trans-4,4'-azobis(pyridine) 
• 1122-96-9 4-methoxypyridine N-oxide 
• 14474-56-7 4-ethoxypyridine-N-oxide 
• 6890-62-6 4-hydroxypyridine N-oxide 
• 31872-57-8 3-Nitro-4-hydroxy-pyridin-N-oxid 
• 856846-18-9 N-(1-acetyl-[4]piperidyl)-acetamide 
• 33421-08-8 4-phenylsulfanyl-pyridine-1-oxide 
• 139-66-2 diphenyl sulfide 
• 1121-76-2 4-chloropyridine N-oxide 
• 2683-66-1 4-benzyloxypyridine-N-oxide 
• 33399-53-0 4-phenoxypyridine N-oxide 
• 504-24-5 4-aminopyridine 
• 19808-51-6 1,2-di(pyridin-4-yl)hydrazine 

Relevant articles and documents

Single component N-O chelated arylnickel(II) complexes as ethene polymerisation and CO/ethene copolymerisation catalysts. Examples of ligand induced changes to the reaction pathway

Arylnickel(II) phosphine complexes containing substituted N-O bidentate ligands, of the type [NiR(N-O)L] [N-O = 4-nitropyridine-2-carboxylate (4-NO2-pyca), R = 0-tolyl, L = PPh3; N-O = 2-pyrazinecarboxylate (pyzca), R = 0-tolyl, L = PPh3; and N-O = 4-methoxypyridine-2-carboxylate (4-MeO-pyca), R = 0-tolyl, L = PPh3] have been prepared and characterised. Single crystal X-ray studies of the complexes [Ni(0-tolyl)(pyca)PPh3], 1, and the isomorphous analogue [Ni(0-tolyl)(4-NO2-pyca)PPh3], 3, show the expected square planar coordination about the nickel centres, with the pyridine nitrogens being trans to the phosphine ligand for both compounds. The coordination spheres of the two complexes are very similar, no elongation of the Ni-N bond for complex 3, which contains the 4-NO2-pyca ligand, being evident. In complex 3 the 0-tolyl ligand is disordered over two sites indicating the presence, in the solid state, of two conformers in which the 0-methyl groups of 0-tolyl are located to either side of the coordination plane. The complexes with substituted pyca ligands form single component catalysts for the conversion of ethene to high molecular weight polyethene and for the copolymerisation of ethene and carbon monoxide to polyketone under mild conditions. The nature of the product, whether predominantly high molecular weight polymer or a mixture of polymer and lower oligomer, is dependent on the basicity of the N-O chelate ligand. From an NMR study of the effect of added ethene on the complex [Ni(0-tolyl)(4-NO2-pyca)PPh3], a mechanism involving alkene promoted ligand dissociation is suggested.

A Practical Approach of Continuous Processing to High Energetic Nitration Reactions in Microreactors

Continuous processing in microreactors represents a novel way for the safe and expedient conduct of high energetic reactions and potentially hazardous chemistry. Apart from handling benefits (such as minimised problems in the scale-up process), reactions in microreactors proceed under precisely controlled conditions providing improved yields and product quality compared to the batch procedure. In this paper, the potential of this technology is exemplarily determined in the crucial nitration of the pharmaceutically relevant intermediate 1-methyl-3-propyl-1H-pyrazole-5-carboxylic acid (1). Further fundamental nitration examples demonstrate the unproblematic handling of hazardous H2SO4/ HNO3 mixtures for the nitration of 2-methylindole (4) and pyridine- N-oxide (6) or even the explosive acetyl nitrate Ac2O/HNO3 (nitration of toluene, 8) in the continuous reaction mode.

Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines

Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional molecules such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.

Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine: N -oxides

A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C-H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63-92%; 19 examples). In the cases of 3-substituted PyO, the C-H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.

A two-step continuous flow synthesis of 4-nitropyridine

4-Nitropyridine, a key intermediate in medicinal products, was successfully prepared from pyridine N-oxide in a two-step -approach. Pyridine N-oxide was nitrated with HNO3 and H2SO4 to give 4-nitropyridine N-oxide, followed by reaction with PCl3 to give the final product. The continuous flow methodology was used to minimise accumulation of the highly energetic and potentially explosive nitration product to enable the safe scale-up of 4-nitropyridine with no 2-nitropyridine by-product. By employing continuous extraction in the nitration step and applying the optimised conditions, a throughput of 0.716 kg 4-nitropyridine product per day from pyridine N-oxide with 83% yield and high selectivity in a continuous flow system was achieved.

Metal-free methylation of a pyridine N-oxide C-H bond by using peroxides

Metal-free methylation of a pyridine N-oxide C-H bond was developed using peroxide as a methyl reagent under neat conditions. Pyridine N-oxide derivatives with various groups (e.g., Cl, NO2, and OCH3) were all suitable substrates, and the desired products were obtained in moderate to excellent yields under standard conditions. Moreover, the methylation can be performed with a good yield on the gram-scale experiment. Tentative mechanistic studies show that the methylation is a classical radical process.

PROCESS FOR THE PREPARATION OF FAMPRIDINE

The present invention relates to a process for the preparation of substantially pure fampridine compound of structural formula (I), (II), (III) comprising nitrifying pyridine-N-oxide hydrochloride with suitable nitrating agent; reducing with suitable reducing agent and purifying by recrystallizing in water followed by treating with an alkyl acetate solvent.

Syntheses of sterically hindered zwitterionic pyridinium phenolates as model compounds in nonlinear optics

Pyridinium phenolates possess a dissymmetric delocalised π-electron system providing a huge quadratic nonlinearity. They are a promising class of molecules for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds. The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates 2a-e bearing two tert-butyl substituents at the ortho position(s) of the phenolate functionality. Such bulky groups would enhance the solubility of zwitterions in organic solvents and would limit the formation of aggregates. Their efficient preparations by using Suzuki cross-coupling reactions involving 3,5-dialkylated 4-bromopyridine N-oxides are described herein. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Preparation, characterization, and aquation kinetics of pyridine N-oxide complexes of chromium(III)

A series of (H2O)5Cr(X-pyO)3+ ions (pyO = pyridine N-oxide, X = H, 3-CH3, 4-CH3, 4-OCH3, 4-NO2) were prepared by the reduction of the corresponding pyridine N-oxide adducts of diperoxochromium(VI) species with acidic ferrous perchlorate. The (H2O)5Cr(X-pyO)3+ complexes undergo aquation to yield Cr(H2O)63+ and X-pyO according to the rate law kobs = ko + k -1[H+]-1. The values of the rate constants extrapolated to 298 K at 1.0 M ionic strength are: k0 = 2.80 × 10-6 s-1, k-1 = 1.86 × 10-8 M s-1 (X = 4-NO2); 7.80 × 10-8, 6.27 × 10-10 (H); 4.80 × 10-8, 3.20 × 10 -10 (3-CH3); 3.05 × 10-8, 1.60 × 10-10 (4-CH3); and 2.37 × 10-9, 4.76 × 10-11 (4-OCH3). The reaction of the 4-OCH 3 complex exhibits two additional terms in the rate law, k 1[H+] + k-2[H+]-2. The binding of 4-OCH3-pyO to chromium is suggested to take place through the methoxy group. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Microreaction technology as a novel approach to drug design, process development and reliability

This paper focuses on the application of microreaction technology in the life science industry. Certain features of microreaction technology, for example, mixing, heat transfer, and residence time distribution, are discussed. Important advantages such as high operational safety and the possibility to transfer the experimental results directly from laboratory to the production of pilot-plant scales are mentioned. Potential application fields in the drug discovery and development processes, from research to production, by including chemical synthesis of different targets in the case of the quinoline acid derivative (ciprofloxacin) and the Paal - Knorr pyrrole synthesis are presented.