5320-98-9

Usage

Uses

Used in Chemical Synthesis:
4-(O-NITROPHENYL)MORPHOLINE is used as a reactant for [application reason] in the palladium-catalyzed amination of aryl nonaflates. This application takes advantage of its reactivity to facilitate the formation of new chemical bonds and create a range of products in the field of organic chemistry.
If there are different applications in different industries, they are listed separately:
Used in Pharmaceutical Industry:
4-(O-NITROPHENYL)MORPHOLINE is used as an intermediate for [application reason] in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a valuable building block in the development of new drugs and medications.
Used in Research and Development:
4-(O-NITROPHENYL)MORPHOLINE is used as a research compound for [application reason] in the exploration of new chemical reactions and mechanisms. It serves as a useful tool for scientists to study and understand the behavior of different chemical groups and their interactions with other molecules.

InChI:InChI=1/C10H12N2O3/c13-12(14)10-4-2-1-3-9(10)11-5-7-15-8-6-11/h1-4H,5-8H2

Upstream product

• 110-91-8 morpholine 
• 577-19-5 2-nitrophenyl bromide 
• 609-73-4 o-nitroiodobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 132993-22-7 2-nitrophenyl trifluoromethanesulfonate 
• 342589-38-2 2-nitrophenyl nonaflate 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 13368-42-8 4-(trimethylsilyl)morpholine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-75-5 2-hydroxynitrobenzene 
• 874480-23-6 C₁₂H₈N₂O₄Zn 
• 552-16-9 ortho-nitrobenzoic acid 
• 17264-82-3 sodium 2-nitrobenzoate 
• 15163-59-4 potassium o-nitrobenzoate 

Downstream Products

• 5585-33-1 2-morpholinoaniline 
• 27386-34-1 3,4-dihydro-1H-benzo[4,5]imidazo[2,1-c][1,4]oxazine 10-oxide 
• 78019-83-7 N-(2-nitrophenyl)-morpholine N-oxide 
• 338949-23-8 1-(2-nitrophenyl)morpholine-2-carbonitrile 
• 5638-73-3 3,4-dihydro-1H-benzo[4,5]imidazo[2,1-c][1,4]oxazine 
• 1173462-16-2 phenyl (2-morpholinophenyl)carbamate 
• 400076-83-7 2-chloro-N-(2-morpholinophenyl)nicotinamide 
• 78019-99-5 4-(2-Nitro-phenoxy)-morpholine 

Relevant academic research and scientific papers

Palladium nanoparticles supported on cysteine-functionalized MNPs as robust recyclable catalysts for fast O- and N-arylation reactions in green media

A magnetically robust recyclable nanocatalyst was fabricated by immobilizing of Pd onto the surface of cysteine-functionalized magnetic nanoparticles (MNPs?Cys-Pd). This nanocatalyst was characterized using various techniques such as FT-IR, XRD, TEM, SEM, EDX, VSM, and ICP. The application of catalyst (MNPs?Cys-Pd) was investigated for O-arylation and N-arylation reactions. This phosphine-free complex was found as highly efficient heterogeneous catalyst in green media and mild reaction conditions. In addition, it gave excellent recyclability without significant deactivation after ten cycles.

Decarboxylative ipso Amination of Activated Benzoic Acids

In the presence of a bimetallic Pd/Cu system with 1,10-phenanthroline as the ligand and either air or N-methylmorpholine N-oxide as the oxidant, electron-deficient benzoic acids undergo oxidative decarboxylative coupling with unprotected amines. This operationally simple aniline synthesis is widely applicable with respect to the amine and gives good yields, even on multigram scale. The orthogonality of this reaction to other Pd-catalyzed cross-couplings allows the concise synthesis of multisubstituted arenes by sequential C?C, C?Cl, and C?N functionalizations. Mechanistic investigations suggest the intermediacy of a hypervalent Pd species.

HEAT SHOCK PROTEIN 90 INHIBITORS

Substituted aromatic compounds of formula (I) shown below: (formula I) The definition of each variable in formula (I) appears in the Specification. Also disclosed is a pharmaceutical composition containing one of the substituted aromatic compounds. Further disclosed is a method of using one of these compounds for treating a medical condition associated with HSP90.

Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)

Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFRα) kinases play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFRα dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRα. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PDGFRα-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 μM concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T670I tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.

Carbazole and Carboline Compounds for Use in the Diagnosis, Treatment, Alleviation or Prevention of Disorders Associated with Amyloid or Amyloid-Like Proteins

The present invention relates to novel compounds that can be employed in the diagnosis, treatment, alleviation or prevention of a group of disorders and abnormalities associated with amyloid proteins and amyloid-like proteins, such as Alzheimer's disease. Precursors for the preparation of the compounds according to the present invention are also provided.

A Structure–Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki–Miyaura Coupling Reactions

A new series of Ni NNN pincer complexes were synthesized and characterized. The main difference among these complexes is the substituents on the side arm amino group(s). No major structural difference was found except for the C–N–C angle of the various substituents and the ‘pseudo bite angle’ of the complexes. Four new complexes were efficient for the alkyl-alkyl Kumada reaction of primary alkyl halides, and among them, one complex was also efficient with secondary alkyl halides. The influence of the substituents on the catalytic performance of the Ni complexes in alkyl-alkyl Kumada and Suzuki–Miyaura cross-coupling reactions was systematically investigated. No correlation was found between the catalytic activity and the key structural parameters (C–N–C angle and ‘pseudo bite angle’), redox properties or Lewis acidity of the complexes.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

First Application of Heterogeneous Cobalt Catalysis in Csp2-N Cross-Coupling of Activated Chloroarenes under Ligand-Free Conditions

A heterogeneous CoII/Al2O3 catalyst efficiently catalyses the N-arylation of N-heterocycles and open-chain secondary amines by activated chloroarenes and chloroheteroarenes under ligand-free conditions in water to give a series of functionalized tertiary amines. The catalyst was prepared by immobilizing CoBr2 onto the surface of Al2O3, and was characterized by X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscopy, and energy-dispersive X-ray analysis. This catalyst could be recycled up to six times without any appreciable loss of catalytic activity. A heterogeneous CoII/Al2O3 catalyst efficiently catalyses the N-arylation of N-heterocycles and open- or closed-chain secondary amines by activated chloroarenes and chloroheteroarenes under ligand-free conditions in water to give a series of functionalized tertiary amines.

Synthesis, antifungal activity and QSAR of some novel carboxylic acid amides

A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC50 = 16.75 μg/mL) and Rhizoctonia solani (EC50 = 19.19 μg/mL), compared to the reference compound boscalid with EC50 values of 10.68 and 14.47 μg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.