17076-68-5

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-NITROPHENOXY)BENZONITRILE is used as a chemical intermediate for the synthesis of new drugs, given its potential to contribute to the development of biologically active compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(4-NITROPHENOXY)BENZONITRILE is utilized as a precursor in the production of pesticides, highlighting its role in creating effective and novel agrochemicals.
Used in Materials Science:
4-(4-NITROPHENOXY)BENZONITRILE is employed in materials science for its potential applications in creating new materials, taking advantage of its unique chemical structure and properties.
Used as a Reagent in Organic Chemistry Reactions:
4-(4-NITROPHENOXY)BENZONITRILE also serves as a reagent in various organic chemistry reactions, facilitating important processes in the synthesis of complex organic molecules.
Due to its diverse applications and the potential for further research and development, 4-(4-NITROPHENOXY)BENZONITRILE holds significant interest for scientists across different fields.

InChI:InChI=1/C13H8N2O3/c14-9-10-1-5-12(6-2-10)18-13-7-3-11(4-8-13)15(16)17/h1-8H

Upstream product

• 117635-43-5 tert-butyl(4-(1-isocyanovinyl)phenoxy)dimethylsilane 
• 350-46-9 4-Fluoronitrobenzene 
• 2687-40-3 4-nitrophenyl 4'-acetamidophenyl ether 
• 90149-61-4 p-cyanophenyl n-dodecanoate 
• 636-98-6 p-nitrobenzene iodide 
• 767-00-0 4-cyanophenol 
• 3328-57-2 sodium 4-cyanophenolate 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 86031-12-1 bis(4-cyanophenyl)carbonate 
• 586-78-7 para-nitrophenyl bromide 
• 35719-43-8 potassium salt of 4-acetamidophenol 
• 100-00-5 4-chlorobenzonitrile 
• 100-25-4 para-dinitrobenzene 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 17076-69-6 4-amino-4'-cyanodiphenyl ether 

Relevant academic research and scientific papers

P(i-BuNCH2CH2)3N: An efficient promoter for the nucleophilic aromatic substitution reaction of aryl fluorides with aryl TBDMS (or TMS) ethers

(Chemical Equation Presented) The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and aryl TBDMS (or TMS) ethers has been shown to be efficiently promoted by proazaphosphatranes such as P(i-BuNCH2CH2)3N (3). Excellent yields of diaryl ether products were obtained under unusually mild conditions.

Synthesis and evaluation of aminobenzothiazoles as blockers of N- and T-type calcium channels

Both N- and T-type calcium ion channels have been implicated in pain transmission and the N-type channel is a well-validated target for the treatment of neuropathic pain. An SAR investigation of a series of substituted aminobenzothiazoles identified a subset of five compounds with comparable activity to the positive control Z160 in a FLIPR-based intracellular calcium response assay measuring potency at both CaV2.2 and CaV3.2 channels. These compounds may form the basis for the development of drug leads and tool compounds for assessing in vivo effects of variable modulation of CaV2.2 and CaV3.2 channels.

Ullmann reaction through ecocatalysis: Insights from bioresource and synthetic potential

We report the elaboration of novel bio-sourced ecocatalysts for the Ullmann coupling reaction. Ecocatalysis is based on the recycling of metals issued from phytoremediation or rehabilitation, and an innovative chemical valorization of the subsequent biomass in the field of catalysis. Here, we describe efficient copper accumulation by plants via phytoextraction and rhizofiltration. These phytotechnologies were revisited to demonstrate a novel potential of these natural resources for green chemistry. Taking advantage of the remarkable ability of the selected plants to accumulate Cu(ii) species into their roots or leaves, the latter can be directly used for the preparation of ecocatalysts, called Eco-Cu. The formed Eco-Cu catalysts are thoroughly characterized via ICP-MS, IR studies of pyridine sorption/desorption, TEM, XRD, SM and model reactions, in order to elucidate the chemical composition and catalytic activity of these new materials. Significant differences of properties and activities were observed between Eco-Cu and conventional Cu catalysts. Eco-Cu are highly active catalysts in Ullmann coupling reactions with lower Cu quantities compared to known copper catalysts.

CsF/clinoptilolite: An efficient solid base in SNAr and copper-catalyzed Ullmann reactions

CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.

Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors

Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is

Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III

Respiratory chain succinate-ubiquinone oxidoreductase (SQR or complex II) and ubihydroquinone-cytochrome (cyt) c oxidoreductase (cyt bc1 or complex III) have been demonstrated as the promising targets of numerous antibiotics and fungicides. As a continuation of our research work on the development of new fungicides, a series of 1,2,4-triazole-1,3-disulfonamide derivatives with dual functions targeting both SQR and cyt bc1 were designed and synthesized by coupling diverse diphenyl ether moieties with triazolesulfonamide units. These newly synthesized compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectrometry. The in vitro assay indicated that most of the synthesized compounds displayed good inhibition against porcine succinate-cytochrome reductase (SCR) with IC50 values ranging from 3.2 to 81.8 μM, revealing much higher activity than that of the commercial control amisulbrom whose IC50 value is 93.0 μM. Further evaluation against the respective SQR and cyt bc1 indicated that most compounds exhibited SQR-inhibiting activity as well as cyt bc1-inhibiting activity, but the inhibition potency against SQR is much higher than that against cyt bc1, showing that the SCR inhibition might be contributed greatly by the SQR inhibition. The further antibacterial evaluation against Xanthomonas oryzae pv. oryzae revealed that four compounds showed excellent potency at the concentration of 20 μg mL-1. In particular, compounds 6h and 6j exhibited much better antibacterial activity than the commercial control bismerthiazol in terms of their EC50. Impressively, 6j has an EC90 of 33.62 μg mL-1, more than 10-fold higher than that of bismerthiazol.

Room temperature Ullmann type C-O and C-S cross coupling of aryl halides with phenol/thiophenol catalyzed by CuO nanoparticles

C-O/C-S cross coupling of aryl halides with phenol or thiophenol was studied under ligand-free condition at room temperature over CuO nanocatalyst. The scope of the reaction was extended to various aryl halides and substituted phenols under optimized condition. In general, efficient, selective, and reusable heterogeneous nano CuO catalytic system has been developed for room temperature C-O and C-S Ullmann type cross coupling reactions.

Potassium fluoride supported on natural nanoporous zeolite: A new solid base for the synthesis of diaryl ethers

An efficient and inexpensive synthesis of diaryl ethers has been developed. The process involves the nucleophilic aromatic substitution of electron-deficient aryl halides and phenols and is mediated by potassium fluoride/Clinoptilolite (KF/CP) in dimethyl sulfoxide (DMSO). The approach affords good to excellent yields of the arylated products without the need for additional cation capture. The solid base is also efficient in the Ullmann ether synthesis. A new, inexpensive solid base for the synthesis of diaryl ethers has been developed. Clinoptilolite, a natural zeolite with a high tendency for cation capture, combined with potassium fluoride, provides an efficientsolid base for the deprotonation of phenols in nucleophilic reactions. The same solid base acts as a reliable base for the copper-catalyzed synthesis of diaryl ethers. Copyright

Equilibrium shift in the rhodium-catalyzed acyl transfer reactions

Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.

The kinetics and mechanisms of aromatic nucleophilic substitution reactions in liquid ammonia

The rates of aromatic nucleophilic substitution reactions in liquid ammonia are much faster than those in protic solvents indicating that liquid ammonia behaves like a typical dipolar aprotic solvent in its solvent effects on organic reactions. Nitrofluorobenzenes (NFBs) readily undergo solvolysis in liquid ammonia and 2-nitrofluorobenzene is about 30 times more reactive than the 4-substituted isomer. Oxygen nucleophiles, such as alkoxide and phenoxide ions, readily displace fluorine of 4-NFB in liquid ammonia to give the corresponding substitution product with little or no competing solvolysis product. Using the pKa of the substituted phenols in liquid ammonia, the Bronsted βnuc for the reaction of 4-NFB with para-substituted phenoxides is 0.91, indicative of the removal of most of the negative charge on the oxygen anion and complete bond formation in the transition state and therefore suggests that the decomposition of the Meisenheimer σ-intermediate is rate limiting. The aminolysis of 4-NFB occurs without general base catalysis by the amine and the second-order rate constants generate a Bronsted βnuc of 0.36 using either the pKa of aminium ion in acetonitrile or in water, which is also interpreted in terms of rate limiting breakdown of the Meisenheimer σ-intermediate. Nitrobenzene and diazene are formed as unusual products from the reaction between sodium azide and 4-NFB, which may be due to the initially formed 4-nitroazidobenzene decomposing to give a nitrene intermediate, which may then give diazene or be trapped by ammonia to give the unstable hydrazine which then yields nitrobenzene.