60176-19-4

Usage

Uses

Used in Organic Synthesis:
4-(2,5-DIMETHYL-PYRROL-1-YL)-PHENYLAMINE is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the creation of complex molecules with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(2,5-DIMETHYL-PYRROL-1-YL)-PHENYLAMINE is used as a building block for the development of new drugs. Its chemical properties make it suitable for the creation of molecules with potential therapeutic effects, contributing to the advancement of medicine.
Used in Materials Science:
4-(2,5-DIMETHYL-PYRROL-1-YL)-PHENYLAMINE may also have potential applications in the field of materials science. Its unique structure and properties could be utilized in the development of new materials with specific characteristics, such as improved conductivity, stability, or reactivity.
It is important to handle 4-(2,5-DIMETHYL-PYRROL-1-YL)-PHENYLAMINE with care, as it may pose health and environmental risks if not properly managed. Proper safety measures should be taken during its production, use, and disposal to minimize any potential hazards.

InChI:InChI=1/C12H14N2/c1-9-3-4-10(2)14(9)12-7-5-11(13)6-8-12/h3-8H,13H2,1-2H3

Upstream product

• 110-13-4 2,5-hexanedione 
• 106-50-3 1,4-phenylenediamine 
• 5044-22-4 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrole 
• 625-84-3 2,5-Dimethylpyrrole 
• 625-86-5 2,5-dimethylfuran 
• 930-87-0 1,2,5-trimethyl-1H-pyrrole 

Downstream Products

• 136814-89-6 1-(2,5-diethylpyrrol-1-yl)-4-(2,5-dimethylpyrrol-1-yl)benzene 
• 136660-99-6 2,5-dimethyl-1-(4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl)-1Hpyrrole 

Relevant academic research and scientific papers

Direct Synthesis of Pyrroles via Heterogeneous Catalytic Condensation of Anilines with Bioderived Furans

Given the wide applications of pyrroles in agriculture, pharmaceuticals, and supramolecular and materials chemistry, a mild and eco-friendly route to produce functionalized pyrroles from bioderived feedstocks is highly desirable. Described herein is a mild and convenient synthesis of pyrroles via direct condensation of an equimolar amount of structurally diverse anilines with biobased furans catalyzed by a simple and efficient solid acid H form zeolite Y catalyst. The protocol tolerates a large variety of functional groups and offers a general and versatile method for scale-up synthesis of a variety of N-substituted pyrrole compounds. Most importantly, the bioactive pyrrole-derived drug pyrvinium, which has lately been confirmed as highly effective in curing colon cancer, can be obtained by this method.

Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation

A straightforward and solventless synthesis of pyrroles was developed by using mechanochemical activation and a biosourced organic acid as the catalyst. Relative to traditional Paal-Knorr methodologies, various N-substituted pyrroles were obtained in very short reaction times. By reaction with unreactive diketones, desymmetrized aliphatic and aromatic compounds were also synthesized.

Indium-Catalyzed Formal N-Arylation and N-Alkylation of Pyrroles with Amines

Under indium Lewis acid catalysis, a nitrogen atom of N-unsubstituted pyrroles was replaced with a nitrogen atom of primary amines, thereby producing N-aryl- and N-alkylpyrroles. This system formally introducing such carbon frameworks to the pyrrole nitrogen atom shows unique selectivity: only the H?N(pyrrolyl) unit undergoes the N-arylation and N-alkylation even in the coexistence of a similar H?N(indolyl) part; and an aryl–halogen bond remains intact. These are clearly different from the typical method depending on the C?N(pyrrolyl) bond-forming reaction with organic halides as substrates. From a viewpoint of pyrrole N-protection–deprotection chemistry, worth noting is that a methyl group on the pyrrole nitrogen atom can be removed, albeit in a formal way. (Figure presented.).

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents

A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.

Modified Paal-Knorr synthesis of novel and known pyrroles using tungstate sulfuric acid as a recyclable catalyst

Tungstate sulfuric acid (TSA) as a solid acid catalyst has been synthesized and used in Paal-Knorr synthesis of some novel and known pyrroles under solvent-free conditions. Catalyst loadings can be as low as 1 mol percent to give high yields of the corresponding pyrroles at 60 °C. To make the catalyst, sodium tungstic reacted with chlorosulfonic acid in nhexane.

Green and rapid strategy for synthesis of novel and known pyrroles by the use of molybdate sulfuric acid

Molybdate sulfuric acid as a highly efficient catalyst has been employed for the modified Paal-Knorr synthesis of some novel and known pyrroles under solvent-free conditions. Catalyst loads as low as 1 mol % could be used leading to high yields of pure pyrrole derivatives at an oil bath temperature of 60 oC. This method has advantages such as the use of very low amounts of a recyclable catalyst, avoidance of organic solvents, and high product yields.

Electron Spin Resonance Spectroscopy of Pyrrole Radical Cations

The ESR spectra are reported for the radical cations of the following pyrrole derivatives in fluid solution: 2,5-di-t-butyl- and 2,5-diphenyl-pyrrole; N-amino-, N-phthalimido- and N-(4-aminophenyl)-2,5-dimethylpyrrole; 1,4-bis-(2,5-dimethylpyrrol-1-yl)-,