6637-03-2

Usage

Nitroso compound

Contains a nitroso functional group (-N=O)
A nitroso compound is characterized by the presence of a nitroso group (-N=O) in its structure.

Tert-butyl group attachment

Attached to the nitrogen atom (C4H9)
The tert-butyl group, which consists of 4 carbon atoms and 9 hydrogen atoms, is connected to the nitrogen atom in the molecule.

Nitroso group attachment

Attached to the benzene ring
The nitroso group (-N=O) is bonded to the benzene ring, which is a six-membered aromatic ring.

Radical scavenger

Used in organic synthesis, particularly in nitric oxide radical reactions
1-tert-butyl-4-nitrosobenzene is employed to remove or neutralize free radicals in organic synthesis processes, specifically in reactions involving nitric oxide radicals.

Industrial applications

Manufacturing of rubber chemicals, pharmaceuticals, and agrochemicals
The compound is utilized in the production of various chemicals, including those used in the rubber, pharmaceutical, and agrochemical industries.

Chemical intermediate

Acts as a precursor in the synthesis of other compounds
1-tert-butyl-4-nitrosobenzene serves as a starting material or intermediate in the preparation of other chemical compounds.

Upstream product

• 123324-71-0 p-tert-butylphenylboronic acid 
• 3282-56-2 4-tert-butylnitrobenzene 
• 769-92-6 4-tert-Butylaniline 
• 13252-73-8 N-(4-tert-Butylphenyl)hydroxylamine 

Downstream Products

• 1017624-54-2 4-{N-(tert-butylphenyl)-N-hydroxylamino}pyridine 
• 61994-99-8 1,2-bis(4-(tert-butyl)phenyl)diazene oxide 
• 1400663-67-3 4-[(4-tert-butylphenyl)azo]-3-benzeneamine 
• 1400663-74-2 2-(4-(tert-butyl)phenyl)-2H-benzo[d][1,2,3]triazole 
• 1176334-14-7 C₁₆H₁₇IN₂ 
• 1325753-83-0 C₃₆H₄₂N₄ 
• 1325753-80-7 C₃₆H₄₂N₄ 
• 1325753-53-4 C₃₆H₄₂N₄ 
• 1325753-78-3 C₃₄H₃₈N₄ 
• 1325753-76-1 C₃₄H₃₈N₄ 
• 1325753-75-0 C₃₂H₃₄N₄ 
• 1325753-73-8 C₃₂H₃₄N₄ 
• 1325753-49-8 C₃₄H₃₈N₄ 
• 1325753-46-5 C₃₂H₃₄N₄ 

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.

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.

Reversible Photoswitchable Inhibitors Generate Ultrasensitivity in Out-of-Equilibrium Enzymatic Reactions

Ultrasensitivity is a ubiquitous emergent property of biochemical reaction networks. The design and construction of synthetic reaction networks exhibiting ultrasensitivity has been challenging, but would greatly expand the potential properties of life-like materials. Herein, we exploit a general and modular strategy to reversibly regulate the activity of enzymes using light and show how ultrasensitivity arises in simple out-of-equilibrium enzymatic systems upon incorporation of reversible photoswitchable inhibitors (PIs). Utilizing a chromophore/warhead strategy, PIs of the protease α-chymotrypsin were synthesized, which led to the discovery of inhibitors with large differences in inhibition constants (Ki) for the different photoisomers. A microfluidic flow setup was used to study enzymatic reactions under out-of-equilibrium conditions by continuous addition and removal of reagents. Upon irradiation of the continuously stirred tank reactor with different light pulse sequences, i.e., varying the pulse duration or frequency of UV and blue light irradiation, reversible switching between photoisomers resulted in ultrasensitive responses in enzymatic activity as well as frequency filtering of input signals. This general and modular strategy enables reversible and tunable control over the kinetic rates of individual enzyme-catalyzed reactions and makes a programmable linkage of enzymes to a wide range of network topologies feasible.

Rhodium-Catalyzed Reaction of Azobenzenes and Nitrosoarenes toward Phenazines

A rhodium-catalyzed annulative reaction between azobenzenes and nitrosoarenes has been developed, leading to a series of phenazines in moderate to good yields. This procedure proceeds with sequential chelation-assisted addition of aryl C-H to nitrosoarenes and ring closure by electrophilic attack of azo group to aryl. During this transformation, the azo group served as not only a traceless directing group but also a building block in the final products.

Rh(III)-Catalyzed bilateral cyclization of aldehydes with nitrosos toward unsymmetrical acridines proceeding with C-H functionalization enabled by a transient directing group

A Rh(iii)-catalyzed bilateral cyclization was developed for the efficient construction of acridines proceeding with C-H functionalization whereby in situ formation and removal of an imino transient directing group in the presence of catalytic amount of BnNH2 are achieved. In this transformation, a sequential Rh(iii)-catalyzed C-H amination, cyclization, and aromatization process was involved.

Synthesis of 1H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis

Nitrosobenzenes have been used as a convenient aminating reagent for the efficient synthesis of 1H-indazoles via rhodium and copper catalyzed C-H activation and C-N/N-N coupling. The reaction occurred under redox-neutral conditions with high efficiency and functional group tolerance. Moreover, a rhodacyclic imidate complex has been identified as a key intermediate.

Green and controllable metal-free nitrification and nitration of arylboronic acids

A novel and green nitrating reagent has been developed for the nitrification and nitration of arylboronic acids, which can be controlled by the reaction conditions. The process provides an attractive alternative to the traditional nitration protocols.

Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate

Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.

Electronic decoupling approach to quantitative photoswitching in linear multiazobenzene architectures

A strategy to optimize the photoswitching efficiency of rigid, linear multiazobenzene constructs is presented. It consists of introducing large dihedral angles between azobenzene moieties linked via aryl - aryl connections in their para positions. Four bi

Photoswitching vertically oriented azobenzene self-assembled monolayers at the solid-liquid interface

Up or down? Making use of self-assembly, the graphite surface is decorated with upright oriented photochromic units organized by a terfluorene platform. The azobenzenes within the monolayer could be converted from the trans to the cis form leading to substantial and reversible structural reorganization, as revealed by scanning tunneling microscopy (STM) studies. Copyright