36966-84-4

Basic information

• Product Name: N-nitrosoaniline
• CAS NO: 36966-84-4
• Molecular Formula: C₆H₆N₂O
• Molecular Weight: 122.1246
• Mol File: 36966-84-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 181.3°C at 760 mmHg
• Flash Point: 63.5°C
• Density: 1.14g/cm³
• Vapor Pressure: 0.857mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: N-nitrosoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-nitrosoaniline(36966-84-4)
• EPA Substance Registry System: N-nitrosoaniline(36966-84-4)

Safety Data

• Hazardous Substances Data: 36966-84-4(Hazardous Substances Data)

Usage

General Description

N-nitrosoaniline, also known as N-phenylnitrous amine, is a chemical compound with the formula C6H6N2O. It is a pale yellow, crystalline solid that is insoluble in water and soluble in organic solvents. N-nitrosoaniline is classified as a nitrosamine, a group of chemical compounds known to be carcinogenic. It is primarily used in the production of dyes and pigments, as well as in the synthesis of other organic compounds. Exposure to N-nitrosoaniline has been linked to various health hazards, including potential mutagenic and carcinogenic effects. Due to its hazardous nature, strict handling and storage procedures are recommended for this compound.

Upstream product

• 62-53-3 aniline 
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Downstream Products

• 92184-43-5 4-phenylpyridazine 
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• 103150-99-8 5-phenylquinoxaline 
• 5021-43-2 2-phenylquinoxaline 
• 93044-40-7 2-hydroxy-5-nitrobenzaldehydephenylhydrazone 
• 92-52-4 biphenyl 
• 71-43-2 benzene 
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• 3770-50-1 2-carbethoxyindole 
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• 59-88-1 phenylhydrazine hydrochloride 
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• 4827-19-4 (3-nitro-phenyl)-phenyl-diazene 
• 100-34-5 benzene diazonium chloride 

Relevant articles and documents

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.

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.