620-26-8

Usage

Uses

Used in Chemical Industry:
m-Nitrosotoluene is used as an intermediate in the production of various organic compounds and polymers for its ability to facilitate the synthesis of complex molecules.
Used in Dye Manufacturing:
m-Nitrosotoluene is used as a precursor in the manufacturing of dyes, contributing to the development of colorants for various applications.
Used in Pharmaceutical Industry:
m-Nitrosotoluene is utilized in the production of pharmaceuticals, serving as a key component in the synthesis of certain medications.
However, due to its hazardous nature, m-nitrosotoluene can cause irritation to the respiratory system and skin, and prolonged or high-level exposure may lead to more severe health effects. Therefore, it is crucial to implement proper precautions and safety measures when handling or working with m-nitrosotoluene.

InChI:InChI=1/C7H7NO/c1-6-3-2-4-7(5-6)8-9/h2-5H,1H3

Upstream product

• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 82860-26-2 (Z)-di-m-tolyl-diazene-N,N'-dioxide 
• 108-44-1 1-amino-3-methylbenzene 
• 99-08-1 1-methyl-3-nitrobenzene 
• 82860-26-2 Di-m-tolyl-diazene N,N'-dioxide 
• 937-01-9 trimethyl(3-methylphenyl)stannane 

Downstream Products

• 861044-22-6 2,4-dinitro-benzaldehyde-(N-m-tolyl oxime ) 
• 19618-06-5 (E)-di-m-tolyl-diazene-N-oxide 
• 71297-97-7 N,N'-bis(3-methylphenyl)-diazene N-oxide 
• 92022-24-7 (4-bromo-phenyl)-m-tolyl-diazene 
• 2378-65-6 N--N'-fluordiimid-N-oxid 
• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 82860-26-2 (Z)-di-m-tolyl-diazene-N,N'-dioxide 
• 82860-26-2 Di-m-tolyl-diazene N,N'-dioxide 
• 186774-24-3 (η(5)-cyclopentadienyl)[(1,2,3,4,4a,9a-η(6))-fluorenone-(3'-methyl)-anil]iron(II) hexafluorophosphate 
• 186774-54-9 (C₅H₅)Fe(C₆H₅C(C₆H₅)NC₆H₄CH₃)⁽¹⁺⁾*PF₆^(1-)=[(C₅H₅)Fe(C₆H₅C(C₆H₅)NC₆H₄CH₃)]PF₆ 
• 186774-52-7 Z-(η(5)-cyclopentadienyl)[(1,2,2,3,3,4-η(6))-benzophenone-N-(3'-methylphenylnitrone)]iron(II) hexafluorophosphate 
• 56242-85-4 N-(3-methylphenyl)-4-nitrobenzamide 

Relevant academic research and scientific papers

"Photo-Rimonabant": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar " Cis-On" CB1R Antagonist

Human cannabinoid receptor type 1 (hCB1R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and in vitro characterization of "photo-rimonabant", i.e., azo-derivatives of the selective hCB1R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound 16a, which shows marked affinity for CB1R (Ki (cis form) = 29 nM), whose potency increases by illumination with ultraviolet light (CB1R Kitrans/cis ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that 16a is highly selective for hCB1R over hCB2R. These selective antagonists can be valuable molecular tools for optical modulation of CBRs and better understanding of disorders associated with the endocannabinoid system.

Rhodium(III)-catalyzed regioselective C–H nitrosation/annulation of unsymmetrical azobenzenes to synthesize benzotriazole N-oxides via a RhIII/RhIII redox-neutral pathway

A Rh(III)-catalyzed regioselective C–H nitrosation/annulation reaction of unsymmetrical azobenzenes with [NO][BF4] has been developed to achieve high-yielding syntheses of benzotriazole N-oxides with excellent functional group tolerance. Computational studies have revealed that this oxidative C–H functionalization reaction involves an interesting redox-neutral Rh(III)/Rh(III) pathway without the change of Rh oxidation state.

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.

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.

Tungstate-supported silica-coated magnetite nanoparticles: a novel magnetically recoverable nanocatalyst for green synthesis of nitroso arenes

Tungstate ion was heterogenized on the silica-coated magnetite nanoparticles and applied for the selective oxidation of anilines to nitroso arenes—with hydrogen peroxide/urea as oxidant in dimethyl carbonate as solvent—in moderate–good yields (40–96%). The catalyst was characterized using different techniques including Fourier-transform infrared spectroscopy, X-ray powder diffraction, vibrating sample magnetometry, scanning electron microscopy, energy dispersive X-ray and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The catalyst was easily recovered using an external magnet and reused for six times.

A Photoswitchable Agonist for the Histamine H3 Receptor, a Prototypic Family A G-Protein-Coupled Receptor

Spatiotemporal control over biochemical signaling processes involving G protein-coupled receptors (GPCRs) is highly desired for dissecting their complex intracellular signaling. We developed sixteen photoswitchable ligands for the human histamine H3 receptor (hH3R). Upon illumination, key compound 65 decreases its affinity for the hH3R by 8.5-fold and its potency in hH3R-mediated Gi protein activation by over 20-fold, with the trans and cis isomer both acting as full agonist. In real-time two-electrode voltage clamp experiments in Xenopus oocytes, 65 shows rapid light-induced modulation of hH3R activity. Ligand 65 shows good binding selectivity amongst the histamine receptor subfamily and has good photolytic stability. In all, 65 (VUF15000) is the first photoswitchable GPCR agonist confirmed to be modulated through its affinity and potency upon photoswitching while maintaining its intrinsic activity, rendering it a new chemical biology tool for spatiotemporal control of GPCR activation.

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.

Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination

A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.

Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo[d]imidazol-1-amine

A palladium-catalyzed annulation of 2-(aryldiazenyl) aniline and dimethyl sulfoxide was developed to access N-aryl-1H-benzo[d]imidazol-1-amine in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “[dbnd]CH[sbnd]” fragment during this procedure. It represents a facile pathway leading to benzimidazoles.

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.