5585-33-1

Usage

Uses

Used in Chemical Synthesis Industry:
2-MORPHOLINOANILINE is used as an intermediate in the production of dyes and pigments, contributing to the coloration and stability of these substances in various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-MORPHOLINOANILINE is utilized as a precursor in the synthesis of various pharmaceuticals, playing a crucial role in the development of new medications.
Used in Metalworking Fluids:
2-MORPHOLINOANILINE is employed as a corrosion inhibitor in metalworking fluids, enhancing the longevity and performance of these fluids by preventing metal corrosion during industrial processes.
Used in Organic Synthesis:
As a reagent in organic synthesis, 2-MORPHOLINOANILINE facilitates various chemical reactions, enabling the production of a range of organic compounds for different applications.

InChI:InChI=1/C10H14N2O/c11-9-3-1-2-4-10(9)12-5-7-13-8-6-12/h1-4H,5-8,11H2

Upstream product

• 5320-98-9 N-(2-nitrophenyl)morpholine 
• 88-73-3 2-Chloronitrobenzene 
• 1352801-49-0 2-morpholin-4-yl-N-(pivaloyloxy)benzamide 
• 61650-22-4 N-(pivaloyloxy)benzamide 
• 495-18-1 Benzohydroxamic acid 
• 775316-48-8 N-(2-morpholinophenyl)picolinamide 
• 591-50-4 iodobenzene 
• 98-80-6 phenylboronic acid 
• 110-91-8 morpholine 
• 615-36-1 2-bromoaniline 
• 58534-94-4 2-fluoro-3-bromonitrobenzene 
• 348-54-9 2-Fluoroaniline 
• 1493-27-2 ortho-nitrofluorobenzene 
• 62-53-3 aniline 

Downstream Products

• 5321-02-8 2,2'-(2-morpholin-4-yl-phenylazanediyl)-bis-ethanol 
• 5236-95-3 2-Morpholino-N-acetoacetyl-anilin 
• 23257-03-6 2-morpholin-4-yl-N-(4-nitro-benzyl)-aniline 
• 23256-94-2 10-(4-nitro-benzyl)-3,4-dihydro-1H-benzo[4,5]imidazo[2,1-c][1,4]oxazinium; chloride 
• 27224-89-1 2-hydroxy-N-(2-morpholin-4-yl-phenyl)-2-phenyl-acetamide 
• 58785-39-0 (2-morpholin-4-yl-anilino)-butenedioic acid dimethyl ester 
• 58785-52-7 4-(2-morpholin-4-yl-anilino)-pent-3-en-2-one 
• 58785-10-7 (2-morpholin-4-yl-anilinomethylene)-malonic acid diethyl ester 
• 5236-90-8 2,6-dimethyl-4-oxo-4H-pyran-3-carboxylic acid 2-morpholin-4-yl-anilide 
• 27231-15-8 7-morpholin-4-yl-3-phenyl-1,3-dihydro-indol-2-one 
• 131676-81-8 N-(2-morpholinophenyl)butyramidine 
• 131679-35-1 1-(n-butyl)-3-(2-morpholinophenyl)thiourea 
• 131675-72-4 4-[2-(2-piperidinylideneamino)phenyl]morpholine 
• 131676-83-0 N-(2-morpholinophenyl)isobutyramidine 

Relevant academic research and scientific papers

1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates

Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.

Copper-Catalyzed Oxalamide-Directed ortho-C-H Amination of Anilines with Alkylamines

A copper-catalyzed oxalamide-directed ortho-C-H amination of anilines has been developed by using 1 atm of air as the sole oxidant. The protocol shows excellent functional group tolerance, and some heterocyclic amines including indole, benzothiophene, benzothiazole, quinoline, isoquinoline, and quinoxaline could be compatible in the reaction. The late-stage diversification of medicinal drugs demonstrates the synthetic utility of this protocol.

Ru(II)-Catalyzed Amination of Aryl Fluorides via η6-Coordination

We developed a Ru/hemilabile-ligand-catalyzed nucleophilic aromatic substitution (SNAr) of aryl fluorides as the limiting reagents. Significant ligand enhancement was demonstrated by the engagement of both electron-rich and neutral arenes in the SNAr amination without using excess arenes. Preliminary mechanistic studies revealed that the nucleophilic substitution proceeds on a η6-complex of the Ru catalyst and the substrate, and the hemilabile ligand facilitates dissociation of products from the metal center.

Transition-Metal-Catalyzed Amination of Aryl Fluorides

Arene activation via transition-metal (TM) η 6-coordination has merged as a powerful method to diversify the aromatic C-F bond, which is relatively less reactive due to its high bond energy. However, this strategy in general requires to use largely excess arenes or TM η 6-complexes as the substrates. Herein, we highlight our recent work on the catalytic S NAr amination of electron-rich and electron-neutral aryl fluorides that are inert in classical S NAr reactions. This protocol enabled by a Ru/hemilabile ligand catalyst covers a broad scope of substrates without wasting arenes. Mechanistic studies revealed that the nucleo?-philic substitution proceeded on a Ru η 6-arene complex, and the hemilabile ligand significant promoted the arene dissociation.

Copper-Catalyzed Electrophilic Ortho C(sp2)-H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System

A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, b

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, 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.

Synthesis, antifungal activity and structure-activity relationships of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides

A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.