132993-20-5

Basic information

• Product Name: 1-(3-NITRO-PHENYL)-PYRROLIDINE
• Synonyms: TIMTEC-BB SBB006319;1-(3-NITRO-PHENYL)-PYRROLIDINE;1-(Pyrrolidin-1-yl)-3-nitrobenzene
• CAS NO: 132993-20-5
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• Mol File: 132993-20-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 33-34 °C
• Boiling Point: 329.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.233±0.06 g/cm3(Predicted)
• PKA: 3.21±0.40(Predicted)
• CAS DataBase Reference: 1-(3-NITRO-PHENYL)-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-NITRO-PHENYL)-PYRROLIDINE(132993-20-5)
• EPA Substance Registry System: 1-(3-NITRO-PHENYL)-PYRROLIDINE(132993-20-5)

Safety Data

• Hazardous Substances Data: 132993-20-5(Hazardous Substances Data)

Usage

Description

1-(3-Nitro-phenyl)-pyrrolidine, with the molecular formula C11H12N2O2, is a pyrrolidine derivative featuring a 3-nitrophenyl group. This unique structure endows the compound with distinctive chemical properties and reactivity, making it a promising candidate for pharmaceutical and organic synthesis applications. Its potential as a building block in the synthesis of complex organic compounds and as a precursor to drug molecules with pharmacological activity highlights its versatility in research and industrial settings.

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.