13125-93-4

Basic information

• Product Name: Benzene, 1-iodo-4-nitroso-
• CAS NO: 13125-93-4
• Molecular Formula: C6H4INO
• Molecular Weight: 233.008
• Mol File: 13125-93-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Benzene, 1-iodo-4-nitroso-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-iodo-4-nitroso-(13125-93-4)
• EPA Substance Registry System: Benzene, 1-iodo-4-nitroso-(13125-93-4)

Safety Data

• Hazardous Substances Data: 13125-93-4(Hazardous Substances Data)

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 108921-73-9 p-iodonitrosobenzene 
• 540-37-4 p-aminoiodobenzene 
• 5122-99-6 4-iodophenylboronic acid 
• 14454-14-9 N-(4-iodophenyl)hydroxylamine 

Downstream Products

• 478953-22-9 4-(4-iodo-phenylazo)-benzoic acid 
• 636-98-6 p-nitrobenzene iodide 
• 1243003-73-7 C₁₂H₉IN⁽¹⁵⁾NO₂ 
• 108921-73-9 p-iodonitrosobenzene 
• 1243003-56-6 C₁₂H₉IN₂O₂ 
• 1392061-70-9 (3-((4-iodophenyl)diazenyl)phenyl)methanol 
• 1401615-09-5 tert-butyl 3-(5-(1-(3-((4-acetamidophenyl)diazenyl)benzyl)-1H-tetrazol-5-yl)-3-(allyloxy)isoxazol-4-yl)-2-(bis(tert-butoxycarbonyl)amino)propanoate 
• 1392061-74-3 tert-butyl 3-(5-(2-(3-((4-acetamidophenyl)diazenyl)benzyl)-2H-tetrazol-5-yl)-3-(allyloxy)isoxazol-4-yl)-2-(bis(tert-butoxycarbonyl)amino)propanoate 
• 1392061-71-0 N-(4-((3-(hydroxymethyl)phenyl)diazenyl)phenyl)acetamide 

Relevant articles and documents

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.

Mechanochemically induced cross-dimerizations of nitrosobenzenes. Kinetics and solid-state isotope effects

Mechanical treatment (milling) of crystals of aromatic nitroso dimers (azodioxides) induces their dissociation and cross-dimerizations. The mechanisms of these processes are discussed on the basis of kinetic studies and the solid-state 15 N kinetic isotope effect, which is measured for the first time. By comparison with analogous processes in cocrystals and in melts, it appears that the reactions follow similar mechanism in which the surface deformations play the crucial role. The system can also be used as a model for a more general conceptual study of solid-state reaction mechanisms. Copyright