16433-80-0

Basic information

• Product Name: Benzene, 1-ethyl-2-nitroso-
• CAS NO: 16433-80-0
• Molecular Formula: C8H9NO
• Molecular Weight: 135.166
• Mol File: 16433-80-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1-ethyl-2-nitroso-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-ethyl-2-nitroso-(16433-80-0)
• EPA Substance Registry System: Benzene, 1-ethyl-2-nitroso-(16433-80-0)

Safety Data

• Hazardous Substances Data: 16433-80-0(Hazardous Substances Data)

Upstream product

• 612-22-6 2-nitro(ethylbenzene) 
• 578-54-1 ortho-ethylaniline 

Downstream Products

• 78987-16-3 2'-Ethylbenzanilide 
• 98306-73-1 N,N'-bis-(2-ethyl-phenyl)-hydrazine 

Relevant articles and documents

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Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles

Described herein is an imidazole ring formation strategy for the synthesis of axially chiral N-arylbenzimidazoles by means of chiral phosphoric acid catalysis. Two sets of conditions were developed to transform two classes of 2-naphthylamine derivatives into structurally diverse N-arylbenzimidazole atropisomers with excellent chemo- and regioselectivity as well as high levels of enantiocontrol. It is worth reflecting on the unique roles played by the nitroso group in this domino reaction. It functions as a linchpin by first offering an electrophilic site (N) for the initial C?N bond formation while the resulting amine performs the nucleophilic addition to form the second C?N bond. Additionally, it could facilitate the final oxidative aromatization as an oxidant. The atropisomeric products could be conveniently elaborated to a series of axially chiral derivatives, enabling the exploitation of N-arylbenzimidazoles for their potential utilities in asymmetric catalysis.

Synthesis of N -acylamidines via rhodium-catalyzed reaction of nitrosobenzene derivatives with N -sulfonyl-1,2,3-triazoles

α-Imino rhodium carbene, readily generated from N-sulfonyl-1,2,3-triazole, underwent cycloaddition and subsequent rearrangement with a nitrosobenzene derivative to afford N-acylamidine. The unprecedented C-C bond cleavage of α-imino carbene was facilitated by the weakness of the N-O bond.