22955-65-3

Usage

Appearance

Pale yellow to brown liquid

Odor

Strong, aromatic

Primary use

Reagent in chemical reactions (e.g. synthesis of other organic compounds)

Secondary use

Manufacturing of pharmaceuticals and agrochemicals

Classification

Hazardous substance

Safety precautions

Follow all safety guidelines and regulations, proper handling and storage to prevent potential hazards and ensure a safe working environment.

Upstream product

• 100-12-9 4-ethylnitrobenzene 
• 589-16-2 4-aminoethylbenzene 

Downstream Products

• 111272-65-2 2-nitro-fluoren-9-on-[N-(4-ethyl-phenyl)-oxime ] 
• 33227-96-2 p-Ethyl-p'-n-butyloxy-azobenzol 
• 50695-98-2 C₁₇H₂₀N₂O 
• 33227-94-0 p-Ethyl-p'-methoxy-azobenzol 
• 33227-95-1 p-Ethyl-p'-ethoxy-azobenzol 
• 75738-09-9 (4-Ethyl-phenyl)-(4-propyl-phenyl)-diazene 
• 61653-33-6 bis-(4-ethyl-phenyl)-diazene 
• 22955-53-9 C₁₆H₁₅F₂N₃O 
• 23595-86-0 1,2-bis(4-ethylphenyl)diazene oxide 
• 15646-60-3 4-ethyl-azobenzene 
• 1431660-75-1 5-ethyl-3-phenyl-1H-indole 
• 67274-50-4 N-(4-Ethyl-phenyl)-N-hydroxy-acetamide 
• 3663-34-1 N-(4-ethylphenyl)acetamide 

Relevant academic research and scientific papers

The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines

A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho[sbnd] C[sbnd]H functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.

Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts

In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.

Understanding Mechanistic Differences between 3-Diazoindolin-2-Imines and N-Sulfonyl-1,2,3-Triazoles in the Rh2(II)-Catalyzed Reactions with Nitrosoarenes

The employment of α-iminometallocarbenes to construct valuable N-containing compounds has attracted significant research interest. Herein, the nucleophilic addition of nitrosoarenes with the α-imino rhodium carbene species (I), which is derived from Rh2(II)-catalyzed denitrogenation of 3-diazoindolin-2-imines, to produce synthetically useful 2-iminoindolin-nitrones is described. Mechanistically, the N-attack of nitrosoarenes with the carbene site of I is proposed. For the analogous Rh2(II)-catalyzed reaction of nitrosoarenes with N-sulfonyl-1,2,3-triazoles reported by Li and co-workers (Org. Lett. 2014, 16, 6394), however, the O-attack of nitrosoarenes with the carbene site of α-imino rhodium carbene species (II) is more favorable to occur than the N-attack. The subsequent transformation to yield the product of N-acylamidines is rationalized based on computational studies. The mechanistic differences for the reactions of nitrosoarenes with α-imino rhodium carbene species I and II are discussed.

Niobium oxide prepared through a novel supercritical-CO2-assisted method as a highly active heterogeneous catalyst for the synthesis of azoxybenzene from aniline

High-surface area Nb2O5 nanoparticles were synthesised by a novel supercritical-CO2-assisted method (Nb2O5-scCO2) and were applied for the first time as a heterogeneous catalyst in the oxidative coupling of aniline to azoxybenzene using the environmentally friendly H2O2 as the oxidant. The application of scCO2 in the synthesis of Nb2O5-scCO2 catalyst resulted in a significantly enhanced catalytic activity compared to a reference catalyst prepared without scCO2 (Nb2O5-Ref) or to commercial Nb2O5. Importantly, the Nb2O5-scCO2 catalyst achieved an aniline conversion of 86% (stoichiometric maximum of 93% with the employed aniline-to-H2O2 ratio of 1?:?1.4) with an azoxybenzene selectivity of 92% and with 95% efficiency in H2O2 utilisation in 45 min without requiring external heating (the reaction is exothermic) and with an extremely low catalyst loading (weight ratio between the catalyst and substrate, Rc/s = 0.005). This performance largely surpasses that of any other heterogeneous catalyst previously reported for this reaction. Additionally, the Nb2O5 catalyst displayed high activity also for substituted anilines (e.g. methyl or ethyl-anilines and para-anisidine) and was reused in consecutive runs without any loss of activity. Characterisation by means of N2-physisorption, XRD, FTIR and TEM allowed the correlation of the remarkable catalytic performance of Nb2O5-scCO2 to its higher surface area and discrete nanoparticle morphology compared to the aggregated larger particles constituting the material prepared without scCO2. A catalytic test in the presence of a radical scavenger proved that the reaction follows a radical pathway.

Metal-Free Sequential C(sp2)-H/OH and C(sp3)-H Aminations of Nitrosoarenes and N-Heterocycles to Ring-Fused Imidazoles

Hydrogen bond assisted ortho-selective C(sp2)-H amination of nitrosoarenes and subsequent α-C(sp3)-H functionalization of aliphatic amines is achieved under metal-free conditions. The annulation of nitrosoarenes and 2-hydroxy-C-nitroso compounds with N-heterocycles provides a facile excess to a wide range of biologically relevant ring-fused benzimidazoles and structurally novel polycyclic imidazoles, respectively. Nucleophilic aromatic hydrogen substitution (SNArH) was found to be preferred over classical SNAr reaction during the C(sp2)-H amination of halogenated nitrosoarenes.

Reversible switching between self-assembled homomeric and hybrid capsules

We present here the reversible, guest-controlled disproportionation of homomeric and hybrid capsules using photochemistry. The supramolecular containers are self-assembled from shallow and deep cavitand modules.

Tungsten- and molybdenum-based coordination polymer-catalyzed N-oxidation of primary aromatic amines with aqueous hydrogen peroxide

Recyclable tungsten- and molybdenum-based coordination polymers efficiently catalyzed the oxidation of primary aromatic amines to the corresponding nitroso derivatives with 30% aqueous hydrogen peroxide in high yields at room temperature.

Efficient preparation of nitrosoarenes for the synthesis of azobenzenes

(Chemical Equation Presented) Reaction conditions are described for the oxidation of anilines furnishing nitrosoarenes and the synthesis of unsymmetrically substituted azobenzenes. In a comparative study, the catalytic oxidation of methyl 4-aminobenzoate

Catalytic Oxidation of Primary Aromatic Amines to the Corresponding Nitroso Compounds by H2O2 and (hmpa = Hexamethylphosphoric Triamide)

1 catalyses the oxidation of primary aromatic amines to the corresponding nitroso derivatives, in the presence of H2O2 as oxidant.

13C NMR studies of p-substituted nitrosobenzenes

The 13C NMR spectra of a wide range of monomeric para-substituted nitrosobenzenes have been determined end the results related to a wide range of published data for other para-disubstituted benzenes.It is shown that the nitroso substituent exercises a different pattern of effect for the 13C chemical shifts at the ipso C atom from at least twenty eight other substituents.It is noted that when the para substituent is a ?-donor, the nitroso group functions in a different manner from that operative when the para substituent is a ?-acceptor, a general possibility that has already been suggested in the recent literature.