13168-78-0

Basic information

• Product Name: Phenol, 2-nitroso-
• Synonyms: Phenol,o-nitroso- (6CI,7CI,8CI); 2-Nitrosophenol; Orthonitrosophenol; o-Nitrosophenol
• CAS NO: 13168-78-0
• Molecular Formula: C₆H₅NO₂
• Molecular Weight: 123.11
• Mol File: 13168-78-0.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 2-nitroso-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2-nitroso-(13168-78-0)
• EPA Substance Registry System: Phenol, 2-nitroso-(13168-78-0)

Safety Data

• Hazard Codes: 3:
• Safety Statements: x. See also NITROSO COMPOUNDS." target="_blank">Many nitroso compounds are carcinogens. Explodes when heated or on contact with
• Hazardous Substances Data: 13168-78-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenol, 2-nitrosois used as a reagent in organic synthesis for its ability to form stable complexes with various metals. This property makes it useful in metal-catalyzed reactions, facilitating the synthesis of complex organic compounds.
Used in Chemical Industry:
In the chemical industry, Phenol, 2-nitrosois used as a precursor in the production of certain dyes and pharmaceuticals. Its role as a starting material allows for the creation of a variety of chemical products that have specific applications in different fields.

Upstream product

• 71-43-2 benzene 
• 95-55-6 2-amino-phenol 
• 108-95-2 phenol 
• 17075-26-2 2-nitrosoanisole 
• 90-03-9 (2-hydroxyphenyl)mercury chloride 
• 88-75-5 2-hydroxynitrobenzene 
• 7732-18-5 water 
• 7758-99-8 copper(II) sulfate 
• 69-72-7 salicylic acid 
• 7722-84-1 dihydrogen peroxide 
• 7664-93-9 sulfuric acid 
• 599-71-3 piloty's acid 

Downstream Products

• 88-75-5 2-hydroxynitrobenzene 
• 1339219-05-4 (C₆H₄O₂BO)C₆H₄(NO) 
• 833-50-1 2-phenylbenzo[d]oxazole 

Relevant articles and documents

The use of SERS to probe the adsorption and oxidation of o-aminophenol on the silver electrode

Surface-enhanced Raman scattering (SERS) has been used to probe the interaction of o-aminophenol with a silver electrode surface over a wide potential range.No spectrum of adsorbed o-aminophenol has been observed.The SERS spectra were ascribed to the products of o-aminophenol oxidation on the electrode surface at its stationary potential.The main product of oxidation has been identified as 3-aminophenoxazone.Some o-nitrosophenol is also created at the electrode surface.

N-Oxidation of arylamines to nitrosobenzenes using chloroperoxidase purified from Musa paradisiaca stem juice

N-Oxidation of arylamines to their corresponding nitrosobenzenes using a new chloroperoxidase purified from Musa paradisiaca stem juice has been examined. The enzymatic characteristics of the stem chloroperoxidase using 4-chloroaniline as substrate were determined. The Km values for 4-chloroaniline and H2O2 were 770 μM and 154 μM respectively, while the pH and temperature optima were 4.4 and 30°C respectively. The substrate specificities of the enzyme for the arylamines 3,4-dichloroamine, p-aminobenzoic acid, p-toluidine, p-anisidine, m-anisidine, p-aminophenol, o-aminophenol and m-aminophenol have been characterized. The feasibility of using concentrated M. paradisiaca stem juice for the specific conversion of 4-chloroaniline to 4-chloronitrosobenzene has been demonstrated. This enzyme can be used for the N-oxidation of other arylamines.

Selective N-oxidation of aromatic amines to nitroso derivatives using a molybdenum acetylide oxo-peroxo complex as catalyst

The molybdenum acetylide oxo-peroxo complex obtained in situ by the treatment of the corresponding molybdenum acetylide carbonyl complex, CpMo(CO)3(C{triple bond, long}CPh); Cp = η5-C5H5 with H2O2, has been used as an efficient catalyst for selective N-oxidation of primary amines to nitroso derivatives. Excellent amine conversion (up to 100%) and very high selectivity for nitroso compounds (99%) have been obtained using 30% hydrogen peroxide as an oxidant. The oxo peroxo Mo(VI) complex has also been found to be very active for the oxidation of various substituted primary aromatic amines with electron donating as well as electron withdrawing substituents on the aromatic ring.

Nitroso Compounds by Reaction of Organomercurials with Nitrosyl Chloride

By the reaction of RHgX (X = Cl, Br, OAc) with NOCl, mercury is eliminated as ClHgX and, if R is aromatic, nitroso compounds are obtained, i.e., nitrosobenzene, 1-nitrosonaphthalene, 4-nitroso-N,N-dimethylaniline, 2-nitrosophenol, 4-nitrosophenol and methyl 3-nitrososalicylate. If R is aliphatic or alicyclic, with RHgX to NOCl 1:3, gem-chloronitroso compounds are obtained that have not been described previously, i.e., 2-chloro-2-nitrosocyclohexanol, 1-acetoxy-2-chloro-2-nitrosocyclohexane, 1-chloro-2-methoxy-1-nitrosocyclopentane, methyl 2-chloro-2-nitroso-3-methoxypropionate, 1-chloro-1-nitroso-ethane and 2-chloro-2-nitrosoethanol. All products have been characterized by chemical and IR spectral analysis.

Protonation and Acid Catalysed Hydrolysis of Nitrosoaryl Ethers

Studies of the equilibrium protonation and kinetics of acid catalysed hydrolysis of 4-nitrosoanisole, 4-nitrosophenyl phenyl ether and related compounds in dilute aqueous acid and in concentrated aqueous trifluoroacetic acid are reported.Hydrolysis is remarkably facile and occurs by nucleophilic attack of water at the ring carbon bearing the alkoxy or aryloxy substituent of the protonated nitroso aromatic.Direct and indirect pKa determinations for nitroso protonation are reported.

ISOMERIC COMPOSITION OF THE PRODUCTS FROM NITROSATION AND NITRATION OF PHENOL

Under the conditions for the nitrosation of phenol by nitrous acid o-nitrosophenol is converted into the more stable para isomer.On the basis of the established reversibility of the nitrosation reaction and also of the results from investigation into the kinetics of the oxidation of o- and p-nitrosophenols by nitric acid a refined scheme of a "special" mechanism was proposed for the nitration of phenol by dilute nitric acid.By this means it is possible to explain the observed difference in the composition of the products from nitrosation and nitration of phenol and also the effect of nitrous acid on the direction of the latter.The formation of p-nitrosophenol as an intermediate product in the nitration of phenol was demonstrated by a kinetic method.