3535-75-9

Usage

Chemical Properties

Pale Yellow Solid

Safety Profile

Poison by ingestion. When heatedto decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C5H6N2O/c6-5-1-3-7(8)4-2-5/h1-4H,6H2

Upstream product

• 1124-33-0 4-nitraminopyridine N-oxide 
• 10296-38-5 4-azidopyridine N-oxide 
• 100-61-8 N-methylaniline 
• 7783-06-4 hydrogen sulfide 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 7803-57-8 hydrazine hydrate 

Downstream Products

• 504-24-5 4-aminopyridine 
• 14906-56-0 4-Acetamino-pyridin-1-oxid 
• 591754-12-0 N-(2-chloropyridin-4-yl)benzamide 
• 92929-19-6 4-(4-Methoxy-phenyl)-pyridine 1-oxide 
• 92929-17-4 4-(2-methoxyphenyl)pyridine 1-oxide 
• 92929-18-5 4-(3-methoxyphenyl)pyridine 1-oxide 
• 92929-28-7 4-(1-Oxy-pyridin-4-yl)-benzonitrile 
• 92929-26-5 4-(2-cyanophenyl)pyridine 1-oxide 
• 92929-27-6 4.(3-cyanophenyl)-pyridine N-oxide 
• 92929-31-2 4-(4-nitrophenyl)pyridine 1-oxide 
• 92929-30-1 4-(3-nitrophenyl)pyridine 1-oxide 
• 92929-29-8 4-(2-nitrophenyl)pyridine 1-oxide 
• 92929-23-2 4-(2-chlorophenyl)pyridine 1-oxide 
• 92929-20-9 4-(2-methylphenyl)pyridine 1-oxide 

Relevant academic research and scientific papers

Tuning gel state properties of supramolecular gels by functional group modification

The factors affecting the self-assembly process in low molecular weight gelators (LMWGs) were investigated by tuning the gelation properties of a well-known gelator N-(4-pyridyl)isonicotinamide (4PINA). The N—H···N interactions responsible for gel formation in 4PINA were disrupted by altering the functional groups of 4PINA, which was achieved by modifying pyridyl moieties of the gelator to pyridyl N-oxides. We synthesized two mono-N-oxides (INO and PNO) and a di-N-oxide (diNO) and the gelation studies revealed selective gelation of diNO in water, but the two mono-N-oxides formed crystals. The mechanical strength and thermal stabilities of the gelators were evaluated by rheology and transition temperature (Tgel) experiments, respectively, and the analysis of the gel strength indicated that diNO formed weak gels compared to 4PINA. The SEM image of diNO xerogels showed fibrous microcrystalline networks compared to the efficient fibrous morphology in 4PINA. Single-crystal X-ray analysis of diNO gelator revealed that a hydrogen-bonded dimer interacts with adjacent dimers via C—H···O interactions. The non-gelator with similar dimers interacted via C—H···N interaction, which indicates the importance of specific non-bonding interactions in the formation of the gel network. The solvated forms of mono-N-oxides support the fact that these compounds prefer crystalline state rather than gelation due to the increased hydrophilic interactions. The reduced gelation ability (minimum gel concentration (MGC)) and thermal strength of diNO may be attributed to the weak intermolecular C—H···O interaction compared to the strong and unidirectional N—H···N interactions in 4PINA.

Rapid reduction of heteroaromatic nitro groups using catalytic transfer hydrogenation with microwave heating

A method for the rapid, safe reduction of heteroaromatic and aromatic nitro groups to amines is described using catalytic transfer hydrogenation under microwave heating conditions. Commonly available Pd/C or Pt/C catalyst is extremely effective with 1,4-cyclohexadiene as the hydrogen transfer source. In the case of substrates containing potentially labile aromatic halogens, Pt/C is effective and results in little or no dehalogenation. In general, the reactions are complete within 5 min at 120 °C.

Magnesiation of pyridine N-oxides via iodine or bromine-magnesium exchange: A useful tool for functionalizing pyridine N-oxides

Iodo- or 2-bromopyridine N-oxides were readily magnesiated with i-PrMgCl ? LiCl via the iodine or bromine-magnesium exchange. The bromine adjacent to pyridine N-oxide (at the 2- or 6-position) can be regioselectively magnesiated in the presence of other position substituted halogens. This method was tested in various substituted pyridine N-oxide systems, and has been successfully applied to the total synthesis of caerulomycins E and A.

Comparative study of the photochemistry of the azidopyridine 1-oxides

(Chemical Equation Presented) The photochemistry of azidopyridine 1-oxides was studied using an array of glass and matrix isolation techniques. As with room temperature, the photochemistry of 4-azidopyridine 1-oxide is dominated by triplet nitrene chemistry. However, in the case of the 3-azide, matrix photolysis indicates the formation of diazabicyclo[4.1.0]hepta-2,4,6-triene N-oxide and diazacycloheptatetraene N-oxide intermediates as well as triplet nitrene.

New description of substituent effect on electronic spectra by means of substituent constants-VI. Ultraviolet spectra of 4-substituted pyridine N-oxides and blue shifted iodine bands of their EDA complexes with iodine

Electronic spectra of 4-substituted pyridine N-oxides and their EDA complexes with iodine were studied.The substituent effect on the near u.v. 1A1 intramolecular CT bands of the N-oxides and on the blue shifted iodine bands caused by CT complex formation are discussed in terms of a general equation, theoretically derived in order to describe the substituent effect on electronic spectra by means of substituent constants.The results are quite successful and supported by semi-empirical SCFMO-Cl calculations.Based on the results mentioned above, the character of n-? type N-oxide-iodine CT complexes is also examined.The complex formation constants(log K) and pKa values of the N-oxides correlate especially well, indicating that the CT interaction mechanism cannot be neglected in proton addition reactions such as hydrogen bonding and pKa values.

THERMAL AND PHOTOCHEMICAL DECOMPOSITION OF 3- AND 4-AZIDOPYRIDINE 1-OXIDES IN NUCLEOPHILIC SOLVENTS

The thermolysis and photolysis of the title compounds in aniline, N-methylaniline, N,N-dimethylaniline, morpholine and dioxane containing methoxide ion in methanol afforded complex mixtures from which only major products were isolated.No ring-expansion products were detected.In aniline, many of its known oxidation products were found, the N-oxide acting as an oxidizing agent.Hydrogen-abstraction products were the main ones formed from pyridine 1-oxides.

Cosmetic composition for imparting to human skin a coloration resembling a natural tan

A cosmetic composition for imparting to human skin after exposure to sunlight a coloration resembling a natural tan comprising a cosmetic vehicle suitable for topical application to the skin and an effective amount of at least one compound of the formula STR1 wherein R1 represents hydrogen or amino; R2 represents hydrogen, lower alkyl or amino; R3 represents hydrogen, lower alkyl or amino; R4 represents hydrogen, lower alkyl or chlorine; and R5 represents hydrogen, lower alkyl or hydroxy, or amino when R1 is amino, with the proviso that R1, R2 and R3 are not simultaneously amino; and at least one of R1, R2 R3 means amino or an acid addition salt thereof.