22955-65-3

Basic information

• Product Name: 1-ethyl-4-nitrosobenzene
• Synonyms: 1-Ethyl-4-nitrosobenzene; benzene, 1-ethyl-4-nitroso-
• CAS NO: 22955-65-3
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.1632
• Mol File: 22955-65-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 211.9°C at 760 mmHg
• Flash Point: 80.7°C
• Density: 1.01g/cm³
• Vapor Pressure: 0.259mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 1-ethyl-4-nitrosobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethyl-4-nitrosobenzene(22955-65-3)
• EPA Substance Registry System: 1-ethyl-4-nitrosobenzene(22955-65-3)

Safety Data

• Hazardous Substances Data: 22955-65-3(Hazardous Substances Data)

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 

Relevant articles and documents

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.

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.

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.