10220-22-1

Basic information

• Product Name: 1-(4-NITROPHENYL)PYRROLIDINE
• Synonyms: 1-(4-NITROPHENYL)PYRROLIDINE;1-(4-Nitrophenyl)pyrrolidine95%;1-(4-NITROPHENYL)PYRROLIDINE 95%;1-(Pyrrolidin-1-yl)-4-nitrobenzene;pyrrolidine, 1-(4-nitrophenyl)-;4-(Pyrrolidin-1-yl)nitrobenzene
• CAS NO: 10220-22-1
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• Mol File: 10220-22-1.mol

Chemical Properties

• Melting Point: 167-169°C
• Boiling Point: 349.9 °C at 760 mmHg
• Flash Point: 165.4 °C
• Appearance: /
• Density: 1.233 g/cm³
• PKA: 1.30±0.40(Predicted)
• CAS DataBase Reference: 1-(4-NITROPHENYL)PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)PYRROLIDINE(10220-22-1)
• EPA Substance Registry System: 1-(4-NITROPHENYL)PYRROLIDINE(10220-22-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 10220-22-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research Industry:
1-(4-Nitrophenyl)pyrrolidine is used as a research compound for studying its reactivity with oxidizing agents and exploring its potential applications in chemical synthesis and reactions.
Used in Pharmaceutical Industry:
1-(4-Nitrophenyl)pyrrolidine could be used as an intermediate or building block in the synthesis of pharmaceutical compounds, given its unique structure and reactivity.
Used in Material Science:
Due to its aromatic and nitro functional groups, 1-(4-Nitrophenyl)pyrrolidine may be utilized in the development of new materials with specific properties, such as dyes, pigments, or polymers with tailored characteristics.

Upstream product

• 123-75-1 pyrrolidine 
• 100-00-5 4-chlorobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 
• 17763-80-3 para-nitrophenyl triflate 
• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 67-64-1 acetone 
• 586-78-7 para-nitrophenyl bromide 
• 120-94-5 1-Methylpyrrolidine 
• 86396-56-7 methyl 4-((4-nitrophenyl)amino)-4-oxobutanoate 
• 19555-48-7 2-tetrahydropyrrolyl-5-nitrobenzoic acid 
• 350-46-9 4-Fluoronitrobenzene 
• 7335-06-0 1-ethylpyrrolidine 
• 7335-07-1 N-propylpyrrolidine 
• 767-10-2 1-butylpyrrolidine 

Downstream Products

• 2632-65-7 4-pyrrolidin-1-yl-aniline 
• 109142-59-8 (Z) 4,4'-di(pyrrolidin-1-yl)azobenzene 
• 343954-65-4 6-(pyrrolidin-1-yl)quinoline 
• 7664-93-9 sulfuric acid 
• 510723-50-9 4-(4-(pyrrolidin-1-yl)phenylamino)-4-oxobutanoic acid 
• 893087-52-0 1-(4-nitrophenyl)-2-pyrrolidinecarbonitrile 
• 51317-64-7 1-(4-isothiocyanatophenyl)pyrrolidine 

Relevant articles and documents

Palladium-catalysed Heck alkynylation of aryl bromides in an imidazolium ionic liquid: An unexpected subsequent alkyne hydrogenation reaction

The copper-free palladium-catalysed alkynylation of aryl bromides with phenylacetylene in the imidazolium ionic liquid [BMIM][BF4], in the presence of triphenylphosphine ligand and pyrrolidine as a base, was found effective and significantly more chemoselective employing deactivated substrates. When activated aryl substrates were used, unexpected side reactions were observed, especially the subsequent hydrogenation of the alkyne function in some coupling products. In other cases, amine arylation reactions occurred, as illustrated by the formation of pyrrolidinyl-4-nitrobenzene, for which an X-ray diffraction structure is reported. Georg Thieme Verlag Stuttgart.

Cp*Co(iii) and Cu(OAc)2bimetallic catalysis for Buchwald-type C-N cross coupling of aryl chlorides and amines under base, inert gas & solvent-free conditions

A strategy involving bimetallic catalysis with a combination of Cp?Co(CO)I2 and Cu(OAc)2 was used for performing Buchwald-type C-N coupling reactions of aryl chlorides with amines. The reactions proceeded at 100 °C to produce excellent yields of many of the desired C-N coupled products, in 4 h, under aerobic reaction conditions. The reactions were shown to run under base-free and solvent-free conditions, enabling this strategy to work efficiently for electron-withdrawing and base-sensitive functionalities. The presented methodology was found to be equally efficient for electron-donating functionalities as well as for primary (1°) and secondary (2°) aromatic and aliphatic amines. Moreover, the products were easily separated through the extractions of the organic aqueous layer, with this process chromatographic separations is not required.

Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides

An efficient and highly practical procedure is reported for the Ullmann-Goldberg-type copper-catalyzed amination of aryl iodides. By using a combination of copper iodide and proline in the presence of an excess of an amine, a wide range of aryl iodides can be readily aminated at room temperature. The reaction proceeds well regardless of the electronic properties of the starting aryl iodide and the amination products can be obtained without the need for purification by column chromatography in most cases. Owing to its efficiency and the mildness of the reaction conditions, this amination could also be extended to the amination of complex aryl iodides at room temperature.

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.

A palladium nanoparticle-catalyzed aryl-amine coupling reaction: High performance of aryl and pyridyl chlorides as the coupling partner

Carbon nitride (CN)-supported nanosized palladium particles, Pd-CN, have been found to be an active catalyst system for the amination of aryl and pyridyl chloride moieties in the presence of dialkyl amine under mild reaction conditions. The recyclability study of the reaction shows the stable performance of the catalyst without a significant loss of catalytic activity for a couple of cycles.

Microwave-assisted convenient synthesis of N-arylpyrrolidines in water

An efficient and clean synthesis of N-arylpyrrolidines from arylamines and 1,4-dimesyloxybutane was developed using microwave irradiation in an aqueous potassium carbonate medium without any catalyst. The procedure is rapid, simple and convenient.

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.

Growth and characterization of a new organic single crystal: 1-(4-Nitrophenyl) pyrrolidine (4NPY)

A new 1-(4-Nitrophenyl) pyrrolidine single crystal has grown by slow evaporation solution growth technique. The grown crystal have characterized by single crystal X-ray analysis, and it shows that 1-(4-Nitrophenyl) pyrrolidine crystallizes in the orthorhombic space group Pbca, with cell parameters a = 10.3270 (5) A?, b = 9.9458 (6) A?, c = 18.6934 (12) A?, and Z = 8. Powder XRD pattern confirmed that grown crystal posses highly crystalline nature. The functional groups have identified by using FTIR spectral analysis. The absorbance and the luminescence spectra of the title compound have analyzed using UV-Visible and PL spectra. The thermo analytical properties of the crystal have studied using TG/DTA spectrum. The mechanical property of the grown crystal has determined using Vickers micro hardness measurement. The grown features of the crystal have analyzed using etching technique.

Buchwald-Hartwig amination reaction using supported palladium on phosphine-functionalized magnetic nanoparticles

The supported palladium on phosphine-functionalized magnetic nanoparticles (Pd-PFMN) was found to be an efficient magnetically separable catalyst for the Buchwald-Hartwig amination reaction (BHAR) under solvent-free conditions. All of the reactions in the presence of Pd-PFMN catalyst afforded the corresponding products in good to excellent yields. The catalyst can be easily separated from the reaction mixture using an external magnetic field, and it can be reused at least five cycles without significant loss in its initial catalytic activity.

Integrating CuO?Fe2O3 Nanocomposites and Supramolecular Assemblies of Phenazine for Visible-Light Photoredox Catalysis

A photoredox catalytic ensemble consisting of CuO-Fe2O3 nanocomposites and oligomeric derivative of phenazine has been developed. The prepared system acts as an efficient photoredox catalyst for C?N bond formation reaction via SET mechanism under ‘green’ conditions (aerial environment, mixed aqueous media, recyclable), requiring less equivalents of base and amine substrate. The present study demonstrates the significant role of supramolecular assemblies as photooxidants and reductants upon irradiation and their important contribution towards the activation of the metallic centre through energy transfer and electron transfer pathways. The potential of oligomer 4: CuO-Fe2O3 has also been explored for C?C bond formation reactions via the Sonogashira protocol.