932-33-2

Usage

Uses

Used in Pharmaceutical Industry:
Benzene, 1-chloro-2-nitroso-, is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex organic molecules that can have therapeutic effects.
Used in Dye Production:
In the dye industry, Benzene, 1-chloro-2-nitroso-, serves as an intermediate, playing a crucial role in the creation of various dyes that are used in textiles, plastics, and other materials.
Used in Pesticide Production:
Benzene, 1-chloro-2-nitrosois also utilized in the production of pesticides, where it acts as a key intermediate in the synthesis of active ingredients that help control, repel, or kill pests.
Used in Chemical Synthesis:
Benzene, 1-chloro-2-nitroso-, is employed in the synthesis of other chemicals, highlighting its versatility as a building block in organic chemistry for creating a wide range of products.

Upstream product

• 10468-16-3 2-chloro-N-hydroxybenzenamine 
• 88-73-3 2-Chloronitrobenzene 
• 17315-42-3 (CH₃)3SnC₆H₄-o-Cl 
• 95-51-2 o-chloroaniline 
• 142-04-1 aniline hydrochloride 

Downstream Products

• 13556-84-8 2,2'-dichloroazoxybenzene 
• 13556-84-8 2,2'-dichloroazoxybenzene 
• 103906-44-1 2-(2-chloro-phenyl-trans-azo)-pyridine 
• 2285-74-7 N-<2-Chlor-phenyl>-N'-fluordiimid-N-oxid 
• 57892-33-8 2-(2-chloro-phenyl)-3,4-diphenyl-2H-isoxazol-5-one 
• 263-06-9 6H,12H-Dibenzo<1,5>dithiocin 
• 108288-69-3 2-(2-Chlorphenyl)-4H-3,1,2-benzoxathiazin 
• 82344-32-9 N-(o-chlorophenyl)-acetohydroxamic acid 
• 109384-39-6 N-(o-chlorophenyl)formohydroxamic acid 
• 95-51-2 o-chloroaniline 
• 7334-33-0 2,2'-dichloroazobenzene 
• 13556-84-8 2,2'-azoxychlorobenzene 
• 207797-61-3 (η(5)-cyclopentadienyl)[1-9a-η(6)-9-fluorenone-(2'-chloro)-anil]iron(II) hexafluorophosphate 
• 817553-63-2 bis(acetato)bis[2-(3-chloro-2-nitrosophenyl)-(2-chlorophenyl)amide]dipalladium 

Relevant academic research and scientific papers

Transketolase Catalyzed Synthesis of N-Aryl Hydroxamic Acids

Hydroxamic acids are metal-chelating compounds that show important biological activity including anti-tumor effects. We have recently engineered the transketolase from Geobacillus stearothermopilus (TKgst) to convert benzaldehyde as a non-natur

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.

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.

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.

Enantioselective Oxidative Coupling of β-Ketocarbonyls and Anilines by Joint Chiral Primary Amine and Selenium Catalysis

An enantioselective primary amine-catalyzed total N-selective nitroso aldol reaction (N-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% H2O2. This protocol provides a facile and highly efficient access to α-hydroxyamino carbonyls bearing chiral quaternary centers under exceedingly mild and green reaction conditions with high chemo-and enantiocontrol.

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

We report a detailed structure–activity relationship for the scaffold of VUF16216, a compound we have previously communicated as a small-molecule efficacy photoswitch for the peptidergic chemokine GPCR CXCR3. A series of photoswitchable azobenzene ligands was prepared through various synthetic strategies and multistep syntheses. Photochemical and pharmacological properties were used to guide the design iterations. Investigations of positional and substituent effects reveal that halogen substituents on the ortho-position of the outer ring are preferred for conferring partial agonism on the cis form of the ligands. This effect could be expanded by an electron-donating group on the para-position of the central ring. A variety of efficacy differences between the trans and cis forms emerges from these compounds. Tool compounds VUF15888 (4d) and VUF16620 (6e) represent more subtle efficacy switches, while VUF16216 (6f) displays the largest efficacy switch, from antagonism to full agonism. The compound class disclosed here can aid in new photopharmacology studies of CXCR3 signaling.

Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling

The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.

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.

The effect of water on the hydrogenation of o-chloronitrobenzene in ethanol, n-heptane and compressed carbon dioxide

Water as a clean solvent and promoter in the organic synthesis have attracted more attention, herein the effect of water was studied for the hydrogenation of o-chloronitrobenzene (o-CNB) over Pt/C and Pd/C catalysts in ethanol, n-heptane and compressed CO2. Very interesting, the reaction rate decreased in ethanol, but increased in n-heptane and compressed CO 2 with the addition of water. The role of water in the reaction was mainly discussed from the experimental data and phase behavior analysis, one is to activate the functional group of NO2 through the interactions via a hydrogen bonding, and the other is to affect the solubility of hydrogen in ethanol and n-heptane. The positive effect of the interaction between water and reactants may be counteracted by the negative effect of hydrogen solubility in ethanol. However, the concentration of o-CNB and hydrogen changed slightly in n-heptane with the addition of water, so the interaction of water with reactants may play a main role in improving the TOF. The combination of H2O and CO2 is more efficient than the pure H2O, CO 2 and H2O-n-heptane systems. The phase behavior may play important role also for the improved activity except for the interactions of H2O and CO2 with the reactants. o-CNB phase was expanded in the compressed CO2 and so the concentration of H2 in o-CNB phase increased due to the miscible of CO2 and H2, resulting in the enhancement of reaction rate and the maximum conversion at pressure of 9 MPa CO2, at which the volume was expanded to the largest one. The similar results were also obtained in the compressed CO 2 system without H2O. In addition, the stability of Pt/C and Pd/C was studied in H2O-n-heptane and H2O-CO 2. As a result, the H2O-CO2 media and Pt/C catalyst is one of the most effective systems for the hydrogenation of o-CNB.

Synthesis and structural, spectroscopic, and electrochemical characterization of benzo[c]quinolizinium and its 5-aza-, 6-aza, and 5,6-diaza analogues

Four heterocyclic salts 1a-d were prepared by Ca2+-assisted cyclization of fluoro derivatives 3, and investigated by spectroscopic (NMR and UV), electrochemical, and computational (DFT and MP2) methods. The mechanism for the formation of the ca