97608-33-8

Basic information

• Product Name: 3-(2,5-dimethyl-1H-pyrrol-1-yl)phenol
• Synonyms: 3-(2,5-dimethyl-1H-pyrrol-1-yl)phenol
• CAS NO: 97608-33-8
• Molecular Weight: 187.241
• Mol File: 97608-33-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-(2,5-dimethyl-1H-pyrrol-1-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,5-dimethyl-1H-pyrrol-1-yl)phenol(97608-33-8)
• EPA Substance Registry System: 3-(2,5-dimethyl-1H-pyrrol-1-yl)phenol(97608-33-8)

Safety Data

• Hazardous Substances Data: 97608-33-8(Hazardous Substances Data)

Usage

Description

3-(2,5-Dimethyl-1H-pyrrol-1-yl)phenol is an organic compound characterized by the presence of a phenol group attached to a pyrrole ring with two methyl groups at the 2nd and 5th positions. This unique structure endows it with specific chemical properties that make it a valuable intermediate in the synthesis of various compounds.

Uses

Used in Pharmaceutical Industry:
3-(2,5-Dimethyl-1H-pyrrol-1-yl)phenol is used as a reactant in the synthesis of pyrrolone antimalarials for its ability to contribute to the formation of active pharmaceutical compounds that can combat malaria.

Upstream product

• 110-13-4 2,5-hexanedione 
• 591-27-5 m-Hydroxyaniline 

Downstream Products

• 1428183-56-5 C₂₁H₂₂N₂O₄ 
• 878424-24-9 1-(3-hydroxyphenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde 
• 95800-24-1 1-[3-(2-diethylamino-ethoxy)-phenyl]-2,5-dimethyl-pyrrole 

Relevant articles and documents

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.

Discovery and structure-activity relationships of pyrrolone antimalarials

In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 ～ 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.