695-37-4

Basic information

• Product Name: 3-FLUOROPYRIDINE N-OXIDE
• Synonyms: 3-FLUOROPYRIDINE N-OXIDE;3-fluoro-1-oxidanidyl-pyridin-1-ium;3-fluoro-1-oxido-pyridin-1-ium;3-fluoro-1-oxidopyridin-1-ium;3-fluoro-1$l^{5}-pyridin-1-one
• CAS NO: 695-37-4
• Molecular Formula: C₅H₄FNO
• Molecular Weight: 113.09
• EINECS: 1533716-785-6
• Product Categories: Fluorin-contained pyridine series;Pyridine;Pyridines;Fluorine series;alkyl Fluorine
• Mol File: 695-37-4.mol

Chemical Properties

• Melting Point: 65-68°C
• Boiling Point: 275℃
• Flash Point: 120℃
• Appearance: /
• Density: 1.18
• Vapor Pressure: 0.00892mmHg at 25°C
• Refractive Index: 1.494
• PKA: 0.16±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 3-FLUOROPYRIDINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FLUOROPYRIDINE N-OXIDE(695-37-4)
• EPA Substance Registry System: 3-FLUOROPYRIDINE N-OXIDE(695-37-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 695-37-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoropyridine N-oxide is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to enhance the biological activity and selectivity of the resulting compounds. Its unique structure allows for the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
3-Fluoropyridine N-oxide is used as a building block in the synthesis of agrochemicals, such as pesticides and herbicides, to improve their effectiveness in controlling pests and weeds while minimizing environmental impact.
Used in Organic Synthesis:
3-Fluoropyridine N-oxide is used as a reagent in organic synthesis for the preparation of heterocyclic compounds, which are important in various fields, including pharmaceuticals, materials science, and chemical research. Its unique properties enable the synthesis of novel heterocyclic compounds with potential applications in various industries.
Used in Research Applications:
3-Fluoropyridine N-oxide is used in research settings for the development of new synthetic methods and the exploration of its chemical properties. Its mild toxicity and limited environmental impact make it a suitable candidate for research purposes, contributing to the advancement of scientific knowledge in the field of organic chemistry.

InChI:InChI=1/C5H4FNO/c6-5-2-1-3-7(8)4-5/h1-4H

Upstream product

• 372-47-4 3-Fluoropyridine 
• 2402-97-3 3-bromopyridine N-oxide 

Downstream Products

• 151373-12-5 (1-oxy-pyrid-3-ylsulphanyl)-acetic acid methyl ester 
• 372-47-4 3-Fluoropyridine 
• 769-54-0 3-fluoro-4-nitropyridine N-oxide 
• 189100-17-2 3-(4-cyanophenyl)aminopyridine N-oxide 
• 2247-88-3 3-fluoro-pyridin-4-ylamine 
• 89959-07-9 MoO₂(2,6-bis(2,2-diphenyl-2-mercaptoethyl)pyridine^(2-)) 
• 1127562-52-0 2-(3,5-dimethylphenyl)-3-fluoropyridine 1-oxide 
• 1174000-49-7 3-fluoro-2-(4-methoxyphenyl)pyridine 1-oxide 
• 1262526-37-3 2-(4-ethoxycarbonylphenyl)-3-fluoropyridine 1-oxide 
• 1262526-35-1 3-fluoro-2-(3-morpholinophenyl)pyridine 
• 1262526-26-0 2-(4-n-pentylphenyl)-3-fluoropyridine 1-oxide 
• 1262526-38-4 2-{(3,5-dimethoxycarbonyl)phenyl}-3-fluoropyridine 1-oxide 
• 1262526-30-6 3-fluoro-2-(3-methylphenyl)pyridine 1-oxide 
• 1262526-28-2 2-{3-(N,N-dimethylamino)phenyl}-3-fluoropyridine 1-oxide 

Relevant articles and documents

Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes

The photocatalyzed ortho-selective migration on a pyridyl ring has been achieved for the site-selective trifluoromethylative pyridylation of unactivated alkenes. The overall process is initiated by the selective addition of a CF3 radical to the alkene to provide a nucleophilic alkyl radical intermediate, which enables an intramolecular endo addition exclusively to the ortho-position of the pyridinium salt. Both secondary and tertiary alkyl radicals are well-suited for addition to the C2-position of pyridinium salts to ultimately provide synthetically valuable C2-fluoroalkyl functionalized pyridines. Moreover, the method was successfully applied to the reaction with P-centered radicals. The utility of this transformation was further demonstrated by the late-stage functionalization of complex bioactive molecules.

PYRAZINE COMPOUND

PROBLEM TO BE SOLVED: To provide a compound showing improved control activity on various pests or its salt. SOLUTION: The present invention provides a pyrazine compound having a 4-pyridyl group represented by formula (1) or its salt. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Preparation method of halogenated pyridine type nitrogen oxide

The invention discloses a preparation method of a halogenated pyridine type nitrogen oxide. The method comprises the following steps: (1) dissolving a raw material halogenated pyridine into a solvent,adding a certain amount of an oxidizing agent, performing a reaction in a range of a reaction temperature of 0 to 40 DEG C, and after the reaction ends, obtaining a reaction product; (2) performing asubsequent postprocessing step on the reaction product obtained in the step (1) so as to obtain the target product halogenated pyridine type nitrogen oxide. The preparation method disclosed by the invention has the advantages of low reaction temperature, high yield, high purity, low cost and the like.

Strategic Approach on N-Oxides in Gold Catalysis – A Case Study

An extensive kinetic study of selected key reactions of (oxidative) gold catalysis concentrates on the decrease of the catalytic activity due to inhibition of the gold(I) catalyst caused by pyridine derivatives that are obtained as by-products if N-oxides are applied as oxygen donors. The choice of the examined pyridine derivatives and their corresponding N-oxides has been made regardless of their commercial availability; particular attention has been paid to the practical benefit which up to now has been neglected in most of the reaction screenings. The test reactions were monitored by GC and 1H NMR spectroscopy. The received reaction constants provide information concerning a correlation between the electronic structure of the heterocycle and the catalytic activity. Based on the collected kinetic data, it was possible to develop a basic set of three N-oxides which have to be taken into account in further oxidative gold(I)-catalyzed reactions. (Figure presented.).

SYNTHESIS OF META-SUBSTITUTED [18F]-3-FLUORO-4-AMINOPYRIDINES BY DIRECT RADIOFLUORINATION OF PYRIDINE N-OXIDES

Disclosed herein are methods for the fluorination aromatic N-heterocyclic N-oxides that comprise at least one leaving group. The N-oxides may be reduced to the fluorinated aromatic N-heterocyclic amine analogs. This novel fluorination approach may be successfully applied for synthesizing aromatic N-heterocyclic compounds labeled with 18F.

Synthesis method of heterocyclic compound 3-methoxypyridine

The invention discloses a synthesis method of a heterocyclic compound 3-methoxypyridine. The method comprises the following steps: putting raw materials, i.e., 3-halogenated pyridine, hydrogen peroxide and acetic acid into a three-mouth flask, carrying out reaction for 4-8h at the temperature of 40-80 DEG C under the condition of stirring, recovering the acetic acid, adding a saturated sodium carbonate solution and stirring to enable a system to be alkaline, evaporating to remove water, then adding chloroform for washing, and carrying out vacuum distillation to obtain N-oxide-3-halogenated pyridine; respectively adding the N-oxide-3-halogenated pyridine, metal salt of alkyl alcohol, a catalyst A and alcohol into the three-mouth flask, carrying out reflux reaction for 5-8h under the condition of stirring, then cooling, neutralizing a product to be neutral, and carrying out distillation to obtain N-oxide-3-alkyloxypyridine; respectively adding the N-oxide-3-alkyloxypyridine, ferric trichloride, hydrazine hydrate, activated carbon and ethanol into the three-mouth flask, carrying out reaction at the temperature of 70 DEG C for 3h, cooling to room temperature, and carrying out vacuum distillation to obtain the 3-methoxypyridine. The synthesis method is high in intermediate conversion rate, mild in reaction conditions, safe in operation, low in price of raw materials and easy in raw material obtaining, thus being suitable for industrial production.

Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts

We report the first reductive coupling of unactivated alkenes with N-methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts under hydrogen atom transfer (HAT) conditions, and an expanded scope for the coupling of alkenes with N-methoxy pyridinium salts. N-Methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts are accessible in 1-2 steps from the commercial arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from commercial amines (50-85%). In total 36 discrete methoxyheteroarenium salts bearing electron-donating, electron-withdrawing, alkyl, aryl, halogen, and haloalkyl substituents were prepared (several in multigram quantities) and coupled with 38 different alkenes. The transformations proceed under neutral conditions at ambient temperature, provide monoalkylation products exclusively, and form a single alkene addition regioisomer. Preparatively useful and complementary site selectivities in the addition of secondary and tertiary radicals to pyidinium salts are documented: harder secondary radicals favor C-2 addition (2->10:1), while softer tertiary radicals favor bond formation to C-4 (4.7->29:1). A diene possessing a 1,2-disubstituted and 2,2-disubstituted alkene undergoes hydropyridylation at the latter exclusively (61%) suggesting useful site selectivities can be obtained in polyene substrates. The methoxypyridinium salts can also be employed in dehydrogenative arylation, borono-Minisci, and tandem arylation processes. Mechanistic studies support the involvement of a radical process.

Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides

A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.

Synthesis of: Meta -substituted [18F]3-fluoro-4-aminopyridine via direct radiofluorination of pyridine N -oxides

Due to their electron-rich aromatic structure, nucleophilic (radio)fluorination of pyridines is challenging, especially at the meta position. In this paper, we describe the first example of direct fluorination of a pyridine N-oxide to produce a meta fluorinated pyridine. Specifically, fluorination of 3-bromo-4-nitropyridine N-oxide produced in several minutes 3-fluoro-4-nitropyridine N-oxide in moderate yield at room temperature. This intermediate compound was later converted to 3-fluoro-4-aminopyridine easily by catalytic hydrogenation. Furthermore, this approach was successfully applied for labeling with fluorine-18. The use of pyridine N-oxides for the preparation of fluoropyridines is unprecedented in the chemical literature and has the potential to offer a new way for the synthesis of these important structures in pharmaceuticals and radiopharmaceuticals.

COMPOUNDS AND COMPOSITIONS FOR MODULATING EGFR ACTIVITY

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating EGFR activity, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated EGFR activity.