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Usage

Uses

Used in Dye and Pigment Production:
N-nitrosoaniline is used as a chemical intermediate for the production of dyes and pigments. Its unique chemical properties allow it to contribute to the color and stability of these products.
Used in Organic Synthesis:
N-nitrosoaniline is used as a reagent in the synthesis of other organic compounds. Its ability to participate in various chemical reactions makes it a valuable component in the creation of a range of organic substances.
Used in Research and Development:
Due to its chemical properties and potential applications, N-nitrosoaniline is also used in research and development settings to explore new uses and understand its behavior in different chemical environments.

Upstream product

• 62-53-3 aniline 
• 100-34-5 benzene diazonium chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 369-58-4 benzenediazonium hexafluorophosphate 
• 6415-38-9 benzenediazonium sulphate 
• 34885-34-2 phenyldiazonium acetate 
• 118601-01-7 benzenediazonium; tetrachloroarsenic ate(III) 
• 2796-16-9 benzenediazonium; hexafluorosilicate 

Downstream Products

• 92184-43-5 4-phenylpyridazine 
• 92060-44-1 6-phenyl-quinoxaline 
• 103150-99-8 5-phenylquinoxaline 
• 5021-43-2 2-phenylquinoxaline 
• 60-11-7 methyl yellow 
• 586-96-9 Nitrosobenzene 
• 100-34-5 benzene diazonium chloride 
• 92-52-4 biphenyl 
• 71-43-2 benzene 
• 93044-40-7 2-hydroxy-5-nitrobenzaldehydephenylhydrazone 
• 4827-19-4 (3-nitro-phenyl)-phenyl-diazene 
• 2835-59-8 3-(phenyldiazenyl)aniline 
• 3770-50-1 2-carbethoxyindole 
• 4792-54-5 ethyl pyruvate phenylhydrazone 

Relevant academic research and scientific papers

Nanocomposite-based inorganic-organocatalyst Cu(II) complex and SiO2- and Fe3O4 nanoparticles as low-cost and efficient catalysts for aniline and 2-aminopyridine oxidation

Bis-imino Cu(II) complex (CuLAn2), in which the imine ligand (HLAn) acts as a bidentate chelating ligand, was synthesized. The catalytic potential of the inorganic-organocatalyst was studied homogeneously and heterogeneously in the oxidation of aniline and 2-aminopyridine by H2O2 or tBuOOH. Two heterogeneous inorganic-organocatalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were synthesized by the successful immobilization of CuLAn2 on the Fe3O4 surface and the composited Fe3O4 with SiO2, respectively. The heterogeneous structure of those inorganic-organocatalysts was confirmed using Fourier-transform infrared, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, transmission electron microscopy, and magnetic properties. The adsorption–desorption isotherms revealed respectable adsorption parameters (SBET, Vp, and rp). All catalysts exhibited high potential in the oxidation of aniline (with phenylhydroxylamine as the main product) and good potential in the oxidation of 2-aminopyridine, in the first attempt (with 2-nitropyridine-N-oxide and 2-nitrosopyridine-N-oxide as main products), at room temperature. Acetonitrile was found to be the best solvent compared to ethanol, dimethyl sulfoxide, chloroform, and water. The homogeneous catalyst exhibited reusability for three times. The heterogeneous catalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were active for five and seven times, respectively. A mechanism was proposed within electron and oxygen transfer processes.

Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: A new method for synthesis pyranoindoles

A direct and highly stereoselective approach for the synthesis of Z-alkenyl-pyranoindoles had been developed by utilizing Rh(II)-catalyzed intramolecular cyclization of N-sulfonyl-1,2,3-triazoles with indole derivatives. A variety of pyranoindoles were obtained in 44-93% yields. Moreover, a more convenient synthesis of pyranoindoles starting from terminal alkyne was realized via a Cu-Rh sequentially catalyzed one-pot cascade reaction.

Formation of diazohydroxides ArN2OH in aqueous acid solution: Polarographic determination of the equilibrium constant KR for the reaction of 4-substituted arenediazonium ions with H2O

In aqueous acid (pH 2+ decompose spontaneously through the rate-limiting formation of the extremely unstable aryl cation that reacts with any nucleophile present in its solvation shell (D N-‰+-‰AN mechanism). However, in weak acidic and alkaline solutions, ArN2+ react with H2O and OH- at the terminal nitrogen to give azo adducts of the type ArN2OH that are in equilibrium with the parent ArN2 +. The diazohydroxide, in this case an acid, is in equilibrium with its conjugate base, and diazoate ArN2O-. The equilibrium constant for reaction with OH- has been determined for a limited number of ArN2+ from kinetic measurements but not with H2O (KR). Here, we have exploited the electrochemical properties of ArN2+ to determine, for the first time, the equilibrium constants KR of formation of 4-substituted X-ArN 2OH (Xi￡H, Me, MeO, Br, and NO2), which can decompose in several ways including Z-E isomerization or further reaction with OH- to give diazoate ArN2O-. The technique applied was differential pulse polarography, which is very selective and sensitive. The determined pKR values are 5-6, and they are somewhat higher than those obtained for the reaction of ArN2+ with alcohols ROH (pKDE-‰=-‰3-5) under similar acidic conditions. The KR values are not very sensitive to changes in the nature of the substituent in the aromatic ring and a linear Hammett plot with a slope of ρ-‰=-‰0.58 was obtained.

Reductive deamination of aromatic amines with nitric oxide (NO)

Aromatic amines were treated with nitric oxide in tetrahydrofuran or chloroform under argon atmosphere to afford deaminated aromatic compounds in good yields. The reaction is suggested to proceed via aryl radicals, which are supposed to be formed by reduction of aryldiazonium salts with NO.