132993-20-5

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Nitro-phenyl)-pyrrolidine is used as a building block for the synthesis of complex organic compounds and drug molecules, leveraging its unique structure and reactivity to contribute to the development of new pharmaceutical agents with potential therapeutic applications.
Used in Organic Synthesis:
1-(3-Nitro-phenyl)-pyrrolidine serves as a precursor in organic synthesis, where its nitrophenyl group imparts specific chemical and physical properties that are of interest in various research and industrial applications, enhancing the synthesis of novel organic compounds with diverse functionalities.
Used in Research Applications:
In research settings, 1-(3-Nitro-phenyl)-pyrrolidine is utilized for studying its chemical properties and reactivity, providing insights into its potential applications in the development of new materials, catalysts, or other chemical entities with specific properties tailored for various uses.

Upstream product

• 123-75-1 pyrrolidine 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 110-52-1 1,4-dibromo-butane 
• 99-09-2 3-nitro-aniline 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 645-00-1 m-iodonitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 109-99-9 tetrahydrofuran 
• 585-79-5 m-nitrobromobenzene 

Downstream Products

• 115833-93-7 3-pyrrolidin-1-yl-phenylamine 
• 84995-54-0 N-methyl-3-(pyrrolidin-1-yl)aniline 
• 168162-35-4 1-(3-Isocyanato-phenyl)-pyrrolidine 

Relevant academic research and scientific papers

Boron trifluoride-mediated synthesis of N-aryl-substituted pyrrolidines from tetrahydrofuran and amines

[Figure not available: see fulltext.] Boron trifluoride-mediated transformation of tetrahydrofuran to corresponding N-aryl-substituted pyrrolidines is conducted under mild reaction conditions, providing a practical synthetic method with reasonable yields. Computational studies confirmed the reaction mechanism involving a fast Lewis acid-assisted ring-opening step, followed by the 7-membered intermediate formation and a ringclosing process as the rate-determining step.

New N-substituted tetrahydropyrrole derivative synthesis method

The invention provides an amino boron intermediate-mediated synthesis method for preparing N-substituted tetrahydropyrrole derivatives by using aromatic amine and a five-membered oxygen heterocyclic compound as raw materials. According to the present invention, the N-substituted tetrahydropyrrole derivatives are specifically N-aryltetrahydropyrrole and N-aryl 2-methyltetrahydropyrrole, and have the following chemical structure general formulas, wherein Ar is phenyl, 4-methylphenyl, 4-fluorophenyl, 4-chlorophenyl, 2-chlorophenyl, 3-nitrophenyl, 2,4-difluorophenyl, 2,6-dichlorophenyl or 3,5-dichlorophenyl. The present invention discloses the chemical structures and the synthesis method of the compounds.

Titanium tetrachloride-mediated synthesis of N-aryl-substituted azacycles from cyclic ethers

Titanium tetrachloride-mediated transformation of five- and six-membered cyclic ethers to the corresponding N-aryl-substituted azacycles is conducted in moderate to good yields under mild reaction conditions. Computational studies suggested a mechanism involving a Lewis acid-assisted ring-opening, a seven-membered metallacycle intermediate and a ring-closing process facilitated by direct participation of the metal center.

Magnetic silica supported copper: A modular approach to aqueous Ullmann-type amination of aryl halides

One-pot synthesis of a magnetic silica supported copper catalyst has been described via in situ generated magnetic silica (Fe3O 4@SiO2); the catalyst can be used for the efficacious amination of aryl halides in aqueous medium under microwave irradiation.

Antiprion activity of functionalized 9-aminoacridines related to quinacrine

A library of functionalized 6-chloro-2-methoxy-(N9-substituted)acridin-9-amines structurally related to quinacrine were synthesized and evaluated for antiprion activity on four different cell models persistently infected with scrapie prion strains (ScN2a, N167, Ch2) or a human disease prion strain (F3). Most of the compounds were distinguished by the side chain attached to 9-amino of the acridine ring. These were dialkylaminoalkyl and phenyl with basic groups on the phenyl ring. The most promising compound was 6-chloro-2-methoxy-N-(4-(4-methylpiperazin-1-yl)phenyl)acridin-9-amine (15) which had submicromolar EC50 values (0.1-0.7 μM) on all cell models, was able to clear PrPSc at non-toxic concentrations of 1.2-2.5 μM, and was more active than quinacrine in terms of EC50 values. Other promising compounds were 14 (a regioisomer of 15) and 17 which had a 1-benzylpiperidin-4-yl substituent attached to the 9-amino function. Activity was strongly dependent on the presence of a substituted acridine ring, which in this library comprised 6-chloro-2-methoxy substituents on the acridine ring. The side chains of 14, 15, and 17 have not been previously associated with antiprion activity and are interesting leads for further optimization of antiprion activity.

Cadmium(II)-catalyzed C-N cross-coupling of amines with aryl iodides

Cadmium diacetate dihydrate [Cd(OAc)2·2H2O] in combination with ethylene glycol catalyzes efficiently the C-N cross-coupling of amines with aryl iodides by a benzyne mechanism. Alkyl, aryl and heterocyclic amines are compatible with this system affording the aminated products in high to excellent yield.

Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles

A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained.

Anodic cyanation of 1-arylpyrrolidines

The electrochemical cyanation of 1-arylpyrrolidines was carried out in methanol containing sodium cyanide at a platinum anode in a divided cell. The reaction gave the corresponding α-aminonitriles 2, together with the unexpected 1-arylpyrrolidine-2-carboximidic acid methyl esters 3 as byproducts.

Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists

The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.

Mild and efficient copper-catalyzed N-arylation of alkylamines and N-H heterocycles using an oxime-phosphine oxide ligand

A mild and efficient copper-catalyzed system for N-arylation of alkylamines and N-H heterocycles with aryl iodides using a novel, readily prepared and highly stable oxime-functionalized phosphine oxide ligand was developed. The coupling reactions could even be performed in solvent-free conditions with moderate to good yields.