54609-09-5

Usage

Uses

Used in Organic Synthesis:
Phenol, 4-(2,5-dimethyl-1H-pyrrol-1-yl)is utilized as a key building block in organic synthesis for the creation of various pharmaceuticals and biologically active compounds. Its unique structure allows for the development of new molecules with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Phenol, 4-(2,5-dimethyl-1H-pyrrol-1-yl)serves as an important intermediate for the synthesis of drugs. Its chemical properties facilitate the design and synthesis of novel therapeutic agents.
Used in Anticancer Research:
Phenol, 4-(2,5-dimethyl-1H-pyrrol-1-yl)is studied for its potential as an anticancer agent. Its unique structure may contribute to the development of new treatments for various types of cancer.
Used in Antimicrobial Applications:
Phenol, 4-(2,5-dimethyl-1H-pyrrol-1-yl)is also being investigated for its antimicrobial properties, which could lead to the development of new antibiotics or antifungal agents to combat drug-resistant infections.
Used in Research and Development:
Due to its intriguing chemical and biological attributes, Phenol, 4-(2,5-dimethyl-1H-pyrrol-1-yl)is a subject of interest in research and development for uncovering new applications and expanding its use in the scientific and medical fields.

Upstream product

• 123-30-8 4-amino-phenol 
• 110-13-4 2,5-hexanedione 

Downstream Products

• 100149-84-6 1-[4-(2-diethylamino-ethoxy)-phenyl]-2,5-dimethyl-pyrrole 
• 96757-70-9 {2-[4-(2,5-Dimethyl-pyrrol-1-yl)-phenoxy]-ethyl}-dimethyl-amine; compound with toluene-4-sulfonic acid 
• 96783-54-9 {3-[4-(2,5-Dimethyl-pyrrol-1-yl)-phenoxy]-propyl}-dimethyl-amine 
• 1548228-07-4 C₁₇H₂₂N₂O₂ 
• 1548228-19-8 C₁₇H₂₄N₂O 
• 1548228-16-5 C₂₂H₂₆N₄O 
• 1548228-14-3 C₂₃H₂₇N₃O 
• 1548228-09-6 C₁₇H₂₂N₂OS 
• 1548228-05-2 4-(2,5-dimethyl-3-(piperidin-1-ylmethyl)-1H-pyrrol-1-yl)phenol 
• 1548228-12-1 C₁₇H₂₂N₂O 
• 1309752-01-9 4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl dimethylcarbamate 
• 1309752-23-5 (E)-butyl 3-(1-(4-(dimethylcarbamoyloxy)phenyl)-2,5-dimethyl-1H-pyrrol-3-yl)acrylate 
• 207287-79-4 3'-methoxy-[1,1'-biphenyl]-4-amine 
• 92-67-1 4-phenylalanine 

Relevant academic research and scientific papers

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.

An expeditious and highly efficient synthesis of substituted pyrroles using a low melting deep eutectic mixture

An expeditious green method for the synthesis of diverse valued substituted pyrroles through a Paal-Knorr condensation reaction, using a variety of amines and 2,5-hexanedione/2,5-dimethoxytetrahydrofuran in the presence of a low melting mixture ofN,N’-dimethylurea andL-(+)-tartaric acid (which acts as a dual catalyst/solvent system), has fruitfully been revealed. Herein, we have disclosed the applicability of this simple yet effective strategy for the generation of mono- and dipyrroles in good to excellent yields. Moreover,C3-symmetric tripyrrolo-truxene derivatives have also been assembled by means of cyclotrimerization, Paal-Knorr and Clauson-Kaas reactions as crucial steps. Interestingly, the melting mixture was recovered and reused with only a gradual decrease in the catalytic activity (over four cycles) without any significant drop in the yield of the product. This particular methodology is simple, rapid, environmental friendly, and high yielding for the generation of a variety of pyrroles. To the best of our knowledge, the present work reveals the fastest greener method reported up to this date for the construction of substituted pyrroles by utilizing the Paal-Knorr synthetic protocol, achieving impressive yields under operationally simple reaction conditions without involving any precarious/dangerous catalysts or unsafe volatile organic solvents.

Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.

Method for preparing N-aryl pyrrole compound

The present invention relates to a method for preparing an N-aryl pyrrole compound. Furan containing different substituents, aromatic amine containing different substituents and a solid Lewis acid catalyst are mixed and placed in a closed reactor, and an N-aryl pyrrole compound with different substituents is prepared under certain catalytic conditions. The reaction temperature of the catalytic reaction condition is 140-210 DEG C. The solid Lewis acid catalyst is prepared by a sol-gel method, Hf is used as a core metal element, and a mesoporous molecular sieve SBA-15 is used as a carrier. According to the method, the catalyst is simple to prepare, low in cost, high in reaction activity, good in water resistance and structural stability and high in catalytic reaction yield; meanwhile, the Lewis acid type catalyst does not generate acid protons, the corrosion of the catalyst to equipment at high temperature is avoided, the post-reaction treatment is convenient, and the catalyst is renewable and environment-friendly.

Fe3O4@SiO2-PTMS-Guanidine-SA nanoparticles as an effective and reusable catalyst for the synthesis of N-substituted pyrroles

Fe3O4@SiO2-PTMS-Guanidine-SA nanoparticles used as an effective catalyst for the synthesis of N-substituted pyrroles. Pyrroles were synthesized from the reaction between primary amine derivatives and 2,5-hexanedione with high to excellent yields under mild reaction conditions. After completion of the reaction, Fe3O4@SiO2-PTMS-Guanidine-SA magnetic nanoparticles could be recovered easily from the reaction mixture by an external magnet and reused. This catalyst was characterized by FT-IR spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, thermogravimetric analysis and vibrating-sample magnetometry techniques.

A mild and efficient method for the synthesis of pyrroles using MIL-53(Al) as a catalyst under solvent-free sonication

A highly efficient method for the synthesis of pyrroles using MIL-53(Al) as a catalyst has been developed under solvent-free sonication. This reaction has a broad substrate scope and high yields were obtained within a short reaction time. Remarkably, no additional additives and volatile organic solvent are required for this method and the MIL-53(Al) could be recovered and reused several times without significant drop-off in catalytic activity.

Synthesis of Pyrrole Derivatives Promoted by Fe(ClO4)3/SiO2 as an Environmentally Friendly Catalyst

N-Substituted pyrroles have been prepared in high isolated yields (702-99%) by the reaction of hexane-2,5-dione with amines or diamines in the presence of Fe(ClO4)3/SiO2 at ambient temperature under solvent-free conditions. The experimental procedure involves simple operations, and the products are readily separated by short column chromatography. The same reaction of hexane-2,5-dione with amines containing electron-acceptor substituents, such as 4-nitroaniline, resulted in fair yields of pyrrole derivatives.

New nano-Fe3O4-supported Lewis acidic ionic liquid as a highly effective and recyclable catalyst for the preparation of benzoxanthenes and pyrroles under solvent-free sonication

A novel magnetic nanomaterial-immobilized Lewis acidic ionic liquid was successfully synthesized by the covalent embedding of 3-(3-(trimethoxysilyl)propyl)-1H-imidazol-3-ium chlorozincate (ii) ionic liquid to the surface of Fe3O4 nanoparticles. The material was then characterized by FT-IR, SEM, TEM, TGA, ICP-OES, Raman, and EDS. Its performance as a new-generation Lewis acidic catalyst was also examined on the ultrasound-mediated synthesis of benzoxanthenes and pyrroles. Upon completion, the catalyst was simply recovered by an external magnet for multiple reuses without significant lessening of catalytic performance.

A green and efficient method for the synthesis of pyrroles using a deep eutectic solvent ([CholineCl][ZnCl2]3) under solvent-free sonication

An efficient deep eutectic solvent-based synthesis of pyrroles under ultrasound irradiation has been developed to provide a significant improvement of the yield up to 99% in a short reaction time. The synthesis of pyrroles is highly atom-economical, producing water as the sole byproduct. In addition, [CholineCl][ZnCl2]3 is easily synthesized from commercially available choline chloride and zinc chloride via a cost-effective and environmentally benign pathway. The obtained [CholineCl][ZnCl2]3 has been characterized by FT-IR, 1H-NMR, 13C-NMR, HRMS (ESI), Raman, and TGA. Five new pyrroles are synthesized by the current method. Moreover, [CholineCl][ZnCl2]3 could be reused up to four times without significant loss of catalytic activity.

Silica tungstic acid and sulphated silica tungstic acid as highly efficient solid acid catalysts for the synthesis of pyrrole derivatives

In the present study silica supported tungstic acid (STA) and sulphated silica tungstic acid (SSTA) were applied as efficient and cost-effective solid acid catalysts in the synthesis of N-substituted pyrrole derivatives via the Paal–Knorr reaction of 2,5-hexadione with aromatic and aliphatic amines at room temperature. The reaction completed in short time under mild conditions with high yield. The catalysts could be easily recovered upon reaction completion. Structures of all products were confirmed by elemental analysis, FT-IR, 1H and 13C NMR spectra.