637-62-7

Basic information

• Product Name: 4-NITROSOPHENOL
• Synonyms: 4-hydroxyimino-5-cyclohexadien-1-one;p-benzoquinone, monooxime;p-quinone monooxime;Benzoquinone monoxime;N-Hydroxy-p-benzoquinone imine;4-Benzoquinone Monoxime;1,4-Benzoquinone 4-OxiMe;2,5-Cyclohexadiene-1,4-dione 1-OxiMe
• CAS NO: 637-62-7
• Molecular Formula: C₆H₅NO₂
• Molecular Weight: 123.1094
• Product Categories: Aromatics;Miscellaneous Reagents
• Mol File: 637-62-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 216 °C
• Boiling Point: 265.9 °C at 760 mmHg
• Flash Point: 114.6 °C
• Appearance: /
• Density: 1.23 g/cm³
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 6.13±0.10(Predicted)
• CAS DataBase Reference: 4-NITROSOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROSOPHENOL(637-62-7)
• EPA Substance Registry System: 4-NITROSOPHENOL(637-62-7)

Safety Data

• Hazardous Substances Data: 637-62-7(Hazardous Substances Data)

Usage

Uses

4-Benzoquinone MonoxiMe is a reagent used to prepare poly-substituted benzenes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 2774, 1996 DOI: 10.1021/jo951873s

Upstream product

• 10595-51-4 4-nitroso-N-methylaniline 
• 103-90-2 4-acetaminophenol 
• 108-95-2 phenol 
• 104-94-9 4-methoxy-aniline 
• 83933-58-8 N-phenyl-N-(1,1,3,3-tetramethylbutyl)hydroxylamine 
• 123-31-9 hydroquinone 
• 156-10-5 p-nitrosodiphenylamine 
• 659-49-4 4-nitrosoaniline 
• 7664-93-9 sulfuric acid 
• 1516-21-8 4-methoxynitrosobenzene 
• 100-02-7 4-nitro-phenol 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 83933-59-9 N-(4-methoxyphenyl)-N-(1,1,3,3-tetramethylbutyl)hydroxylamine 
• 83933-63-5 N-(1,1,3,3-tetramethylbutyl)-p-benzoquinone imine N-oxide 

Downstream Products

• 57487-06-6 [1]naphthyl-acetic acid-(4-hydroxyimino-cyclohexa-2,5-dienylidenehydrazide) 
• 114720-62-6 [1,4]benzoquinone oxime-semicarbazone 
• 4435-12-5 azophenin 
• 495-73-8 benzoic acid-(4-hydroxyimino-cyclohexa-2,5-dienylidenehydrazide) 
• 1689-82-3 4-hydroxyazobenzene 
• 51-28-5 2,4-Dinitrophenol 
• 100-02-7 4-nitro-phenol 
• 105-11-3 p-benzoquinone dioxime 
• 26271-75-0 3,5-dichloro-4-aminophenol 
• 659-49-4 4-nitrosoaniline 
• 19628-79-6 2,6-dibromo-4-nitrosophenol 
• 6480-66-6 2,6-dichloro-4-methoxyaniline 
• 123-30-8 4-amino-phenol 
• 123-31-9 hydroquinone 

Relevant articles and documents

Superoxo radical scavenging action by common analgesic drug paracetamol: A model kinetic study

In acid perchlorate media ([H+] = 1.0-3.0 M), each mole of paracetamol, HOC6H4NHCOCH3 (APAP), at ambient temperature quantitatively reduces two mole of the metallo-superoxo complex, μ-superoxo-bis[pentaamminecobalt(III)]5+, [(NH3)5Co(III)(μ- O2)Co(III)(NH3)5]5+ (1). Here, complex 1 is reduced to [(NH3)5Co(OH2)]3+, Co2+, O2 and NH4+ and APAP itself is oxidised to quinone oxime and acetic acid. With a large excess of APAP over 1, the reduction follows first-order kinetics. The observed first-order rate constant (ko) increases linearly with increasing [H+] as well as with TAPAP (TAPAP being the analytical concentration of APAP). The protonated form of APAP, viz. APAPH+ seems to be the kinetically reactive reductant species. The enrichment of aqueous reaction media with D2O retards the reaction and thus it appears that the reaction proceeds through an electroprotic mechanism. A relatively small ΔH≠ (57 ± 2 kJ M 1) and moderately negative ΔS≠ (-68±8JK 1 M 1) supports a compact transition state.

Kinetics and Mechanism of Rapid Oxidation of Acetaminophen by Sodium Periodate in the Presence of Catalyst

Abstract: Kinetic studies of the novel oxidation of acetaminophen by sodium periodate are discussed with an emphasis on structure and reactivity by using kinetic approach. The reactions were catalyzed by Os(VIII). The kinetics of the reaction was studied as a function of temperature, ionic strength, dielectric constant of the medium, concentrations of the salt and the added reaction product to learn the mechanism of the reaction. The active species of catalyst and oxidant have been identified. Activation parameters have also been evaluated using the Arrhenius and Eyring plots. A suitable mechanism consistent with the observed kinetic results has been suggested and the related rate law deduced.

The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study

An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.