14305-17-0

Basic information

• Product Name: 2-BROMOPYRIDINE N-OXIDE
• Synonyms: 2-BROMOPYRIDINE N-OXIDE;2-BROMOPYRIDINE OXIDE;6-BROMOPYRIDINE-N-OXIDE;2-Bromopyridine 1-oxide;2-broMopyridine-1-O×ide;Pyridine, 2-broMo-,1-oxide;alpha-Bromopyridine N-oxide;NSC 174129
• CAS NO: 14305-17-0
• Molecular Formula: C₅H₄BrNO
• Molecular Weight: 174
• Product Categories: Pyridines
• Mol File: 14305-17-0.mol

Chemical Properties

• Boiling Point: 336.2°Cat760mmHg
• Flash Point: 157.1°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 0.000223mmHg at 25°C
• Refractive Index: 1.59
• PKA: -0.76±0.10(Predicted)
• CAS DataBase Reference: 2-BROMOPYRIDINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOPYRIDINE N-OXIDE(14305-17-0)
• EPA Substance Registry System: 2-BROMOPYRIDINE N-OXIDE(14305-17-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 14305-17-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Bromopyridine N-oxide is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its unique chemical structure allows for a wide range of chemical reactions, making it a valuable building block in organic synthesis.
Used in Organic Synthesis:
As a building block in organic synthesis, 2-Bromopyridine N-oxide is used for the preparation of a variety of chemical compounds. Its reactivity and functional groups enable it to participate in numerous chemical transformations, facilitating the creation of complex molecules and structures.
Used in Chemoselective Transformations:
2-Bromopyridine N-oxide has been studied for its potential use as a reagent in chemoselective transformations. Its ability to selectively react with specific functional groups makes it a valuable tool in the synthesis of complex organic molecules, where selectivity is crucial for avoiding unwanted side reactions.
Used as a Ligand in Metal-Catalyzed Reactions:
In metal-catalyzed reactions, 2-Bromopyridine N-oxide can act as a ligand, enhancing the catalytic activity and selectivity of the metal center. This application is particularly relevant in the synthesis of pharmaceuticals and other specialty chemicals, where efficient and selective catalytic processes are highly desirable.
Used in Antimicrobial and Antifungal Applications:
Due to its antimicrobial and antifungal properties, 2-Bromopyridine N-oxide has been investigated for its potential as a therapeutic agent in treating certain diseases caused by microbial infections. Its broad-spectrum activity against various pathogens makes it a promising candidate for further research and development.

InChI:InChI=1/C5H4BrNO/c6-5-3-1-2-4-7(5)8/h1-4H

Upstream product

• 109-04-6 2-bromo-pyridine 
• 694-59-7 pyridine N-oxide 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 

Downstream Products

• 89488-29-9 2-bromo-4-methoxypyridine 
• 36710-80-2 2-(4-methoxyphenyl)pyridine N-oxide  
• 33421-24-8 2-(4-methylphenyl)pyridine N-oxide  
• 1131-33-5 2-phenylpyridin N-oxide 
• 39574-22-6 2-phenylthiopyridine nitroxide 
• 39574-20-4 2-benzenesulfonyl-pyridine N-oxide 
• 1394900-18-5 2-(6-bromopyridin-2-yl)phenol 
• 1417626-88-0 C₁₈H₃₀N₄ 
• 1417626-86-8 C₁₈H₃₀N₄O 
• 915006-02-9 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-oxy-pyridin-2-yl)-phenyl]-amide 
• 89943-12-4 4-Amino-2-ethoxy-pyridin 
• 10386-27-3 2-bromoisonicotinonitrile 
• 58530-53-3 2,4-dibromopyridine 

Relevant articles and documents

Development of a novel antidiabetic zinc complex with an organoselenium ligand at the lowest dosage in KK-Ay mice

Diabetes mellitus (DM) is a considerably diagnosed metabolic disease and a serious problem worldwide. We prepared various zinc complexes and studied their potential for use as new antidiabetic agents. In this study, we synthesized a seleniferous zinc complex, di(2-selenopyridine-N-oxidato)zinc(II) ([ZPS]) that has a Zn(Se2O2) coordination mode. Analyses of structure-activity relationships between its insulin-like activity and the coordination mode of [ZPS]-related complexes showed that it had high insulin-like activity. Hypoglycemic effects of [ZPS] on type 2 diabetic KK-Ay mice were exerted at the lowest dose administered (1.25-2.5 mg Zn/kg body weight), unlike previously synthesized zinc complexes. Furthermore, [ZPS] afforded us a new advantage; we were able to investigate the tissue distribution of the ligand by measuring the amount of selenium in the organs of [ZPS]-treated mice. Gastrointestinal absorption and tissue penetration of zinc derived from [ZPS] in ddY mice, which was monitored using an isotope tracer technique, was significantly increased compared to that of ZnCl2. These results suggest that [ZPS] has superior antidiabetic effects compared to previously reported zinc complexes, and is thus a potential novel antidiabetic agent that facilitates the possibility of organoselenium ligands as new metal delivery systems for treating DM.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Method for preparing sulfone and N-oxygen compound by using green and efficient oxidation system

The invention discloses a method for preparing sulfone and N-oxygen compound by using a green and efficient oxidation system. The method comprises the following steps of: by using a tertiary amine compound or aromatic thioether or fatty thioether compound as a raw material, H2O2 as an oxidant, methanol as a reaction solvent and potassium carbonate as an alkali, introducing sulfuryl fluoride 5O2F2gas as an accelerator; performing stirring at room temperature under a sealed condition for oxidation reaction; and after finishing the reaction, filtering to remove solid potassium carbonate, dryingto remove water, filtering to obtain a crude product, and finally carrying out column chromatography separation to obtain a pure product. Tertiary amine is oxidized into an N-oxygen compound, and thethioether is oxidized into sulfone. According to the method, the sulfuryl fluoride (SO2F2) which is very cheap and easy to obtain is used as the reaction promoter, green and environment-friendly hydrogen peroxide (H2O2) is used as an oxidizing agent, and so that the yield of the reaction is generally high; after the reaction, byproducts are only water and inorganic salts (SO4 and F) whichare easy to remove and free of pollution, and the green and efficient oxidation system can be realized, and therefore, the method is suitable for large-scale industrial production.

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.).

Photocatalytic CO2 Reduction by Trigonal-Bipyramidal Cobalt(II) Polypyridyl Complexes: The Nature of Cobalt(I) and Cobalt(0) Complexes upon Their Reactions with CO2, CO, or Proton

The cobalt complexes CoIIL1(PF6)2 (1; L1 = 2,6-bis[2-(2,2′-bipyridin-6′-yl)ethyl]pyridine) and CoIIL2(PF6)2 (2; L2 = 2,6-bis[2-(4-methoxy-2,2′-bipyridin-6′-yl)ethyl]pyridine) were synthesized and used for photocatalytic CO2 reduction in acetonitrile. X-ray structures of complexes 1 and 2 reveal distorted trigonal-bipyramidal geometries with all nitrogen atoms of the ligand coordinated to the Co(II) center, in contrast to the common six-coordinate cobalt complexes with pentadentate polypyridine ligands, where a monodentate solvent completes the coordination sphere. Under electrochemical conditions, the catalytic current for CO2 reduction was observed near the Co(I/0) redox couple for both complexes 1 and 2 at E1/2 = -1.77 and -1.85 V versus Ag/AgNO3 (or -1.86 and -1.94 V vs Fc+/0), respectively. Under photochemical conditions with 2 as the catalyst, [Ru(bpy)3]2+ as a photosensitizer, tri-p-tolylamine (TTA) as a reversible quencher, and triethylamine (TEA) as a sacrificial electron donor, CO and H2 were produced under visible-light irradiation, despite the endergonic reduction of Co(I) to Co(0) by the photogenerated [Ru(bpy)3]+. However, bulk electrolysis in a wet CH3CN solution resulted in the generation of formate as the major product, indicating the facile production of Co(0) and [Co-H]n+ (n = 1 and 0) under electrochemical conditions. The one-electron-reduced complex 2 reacts with CO to produce [Co0L2(CO)] with νCO = 1894 cm-1 together with [CoIIL2]2+ through a disproportionation reaction in acetonitrile, based on the spectroscopic and electrochemical data. Electrochemistry and time-resolved UV-vis spectroscopy indicate a slow CO binding rate with the [CoIL2]+ species, consistent with density functional theory calculations with CoL1 complexes, which predict a large structural change from trigonal-bipyramidal to distorted tetragonal geometry. The reduction of CO2 is much slower than the photochemical formation of [Ru(bpy)3]+ because of the large structural changes, spin flipping in the cobalt catalytic intermediates, and an uphill reaction for the reduction to Co(0) by the photoproduced [Ru(bpy)3]+.

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.

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.

Base free regioselective synthesis of α-triazolylazine derivatives

A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.

Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles

A Mo/P catalytic system for an efficient gram-scale oxidation of a variety of nitrogen heterocycles to N-oxides with hydrogen peroxide as terminal oxidant has been investigated. Combined spectroscopic and crystallographic studies point to the tetranuclear Mo4P peroxo complex as one of the active catalytic species present in the solution. Based on this finding an optimized catalytic system has been developed. The utility and chemoselectivity of the catalytic system has been demonstrated by the synthesis of over 20 heterocyclic N-oxides.

Catalytic N-oxidation of tertiary amines on RuO2NPs anchored graphene nanoplatelets

Ultrafine ruthenium oxide nanoparticles (RuO2NPs) with an average diameter of 1.3 nm were anchored on graphene nanoplatelets (GNPs) using a Ru(acac)3 precursor by a very simple dry synthesis method. The resultant material (GNPs-RuO2NPs) was used as a heterogeneous catalyst for the N-oxidation of tertiary amines for the first time. The transmission electron microscopy (TEM) images of the GNPs-RuO2NPs showed the excellent attachment of RuO2NPs on GNPs. The loading of Ru in GNPs-RuO2NPs was 2.68 wt%, as confirmed by scanning electron microscope-energy dispersive spectroscopy (SEM-EDS). The X-ray photoelectron spectrum (XPS) and the X-ray diffraction pattern (XRD) of GNPs-RuO 2NPs revealed that the chemical state of Ru on GNPs was +4. After the optimization of reaction conditions for N-oxidation of triethylamine, the scope of the reaction was extended to various aliphatic, alicyclic and aromatic tertiary amines. The GNPs-RuO2NPs showed excellent catalytic activity in terms of yields even at a very low amount of Ru catalyst (0.13 mol%). The GNPs-RuO2NPs was heterogeneous in nature, chemically as well as physically, very stable and could be reused up to 5 times. The Royal Society of Chemistry 2014.