53578-11-3

Basic information

• Product Name: 4-Nitro-1-(pyrrolidinocarbonyl)benzene
• Synonyms: 4-Nitro-1-(pyrrolidinocarbonyl)benzene
• CAS NO: 53578-11-3
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22458
• Mol File: 53578-11-3.mol
• Article Data: 50

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Nitro-1-(pyrrolidinocarbonyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-1-(pyrrolidinocarbonyl)benzene(53578-11-3)
• EPA Substance Registry System: 4-Nitro-1-(pyrrolidinocarbonyl)benzene(53578-11-3)

Safety Data

• Hazardous Substances Data: 53578-11-3(Hazardous Substances Data)

Usage

General Description

4-Nitro-1-(pyrrolidinocarbonyl)benzene, also known as NPCB, is a chemical compound with a molecular formula C13H12N2O3. It is a nitroaromatic compound that is often used as a building block in organic synthesis. NPCB is a yellow crystalline solid that is insoluble in water but soluble in organic solvents. It is commonly used in the pharmaceutical industry as a starting material for the synthesis of various drugs and pharmaceutical compounds. NPCB is also used in research laboratories as a reagent for the modification of proteins and peptides. However, it should be handled with care as it is toxic and potentially harmful if ingested or inhaled.

Upstream product

• 123-75-1 pyrrolidine 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 99-99-0 1-methyl-4-nitrobenzene 
• 619-73-8 4-nitrobenzyl chloride 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 555-16-8 4-nitrobenzaldehdye 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 25407-30-1 4-nitrophenacylpyridinium bromide 
• 61273-18-5 4-nitro-benzoic acid-(2,2,2-trichloro-ethyl ester) 
• 25393-54-8 N-(4-nitrobenzoyl)oxazolidinone 
• 122-04-3 4-nitro-benzoyl chloride 
• 168090-27-5 N-(4-nitrobenzoyl)succinimide 
• 636-98-6 p-nitrobenzene iodide 
• 13939-06-5 molybdenum hexacarbonyl 

Downstream Products

• 119741-53-6 1-(4-nitrobenzoyl)pyrrolidin-2-one 
• 56302-41-1 4-carboxamidopyrrolidinophenyl-aniline 
• 1019018-76-8 (4-amino-3-bromo-phenyl)-pyrrolidin-1-yl-methanone 
• 877603-33-3 4-(pyrrolidinylcarbonyl)phenylamine hydrochloride 
• 50903-06-5 (4-nitrophenyl)(pyrrolidin-1yl)methanethione 
• 133851-67-9 1-(4-nitro-benzyl)-pyrrolidine 
• 694-00-8 pyrrolidine-1-d₁ 
• 2906-29-8 4-nitrobenzoate 

Relevant articles and documents

Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites

Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.

Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

A practical catalytic reductive amination of carboxylic acids

We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.