5044-24-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Bromophenyl)-2,5-dimethyl-1H-pyrrole is used as an intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex molecular structures, contributing to the development of new drugs with potential therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(4-Bromophenyl)-2,5-dimethyl-1H-pyrrole is utilized as a precursor in the production of pesticides and other agrochemicals, enhancing their effectiveness in crop protection and management.
Used in Organic Electronics:
1-(4-Bromophenyl)-2,5-dimethyl-1H-pyrrole is employed as a building block in the development of organic electronic materials, such as organic semiconductors and conductors, due to its unique electronic properties and potential for molecular engineering in device applications.

InChI:InChI=1/C12H12BrN/c1-9-3-4-10(2)14(9)12-7-5-11(13)6-8-12/h3-8H,1-2H3

Upstream product

• 110-13-4 2,5-hexanedione 
• 106-40-1 4-bromo-aniline 
• 109-49-9 5-Hexen-2-one 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 74-86-2 acetylene 
• 1333-74-0 hydrogen 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 15898-26-7 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid 
• 83935-45-9 4-(2,5-dimethyl-1H-pyrrol-1-yl)-acetophenone 
• 83756-25-6 2-<4-(2,5-dimethylpyrrol-1-yl)benzilidene>-1,3-dithian 
• 95337-70-5 4-(2,5-dimethylpyrrol-1-yl)benzaldehyde 
• 95337-69-2 1-[1-(4-Bromo-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2,2,2-trifluoro-ethanone 
• 106-40-1 4-bromo-aniline 
• 131817-91-9 (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-2-propenoic acid 
• 1421275-66-2 2,5-dimethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrole 

Relevant academic research and scientific papers

Crystalline salicylic acid as an efficient catalyst for ultrafast Paal–Knorr pyrrole synthesis under microwave induction

Abstract: In this study, the viability of a wide range of crystalline aromatic and aliphatic carboxylic acids as organocatalysts has been investigated for solvent-free Paal–Knorr pyrrole synthesis under microwave activation. Among these potential catalysts, crystalline salicylic acid proved to be a remarkable catalyst because its efficiency remained high even under low microwave power irradiation or a shorter reaction time for the model reaction. The outstanding catalytic activity of salicylic acid allowed the Paal–Knorr cyclocondensation with a turnover frequency up to 1472?h?1 which is unique in the context of a metal-free homogeneous catalysis. The attractive feature of this organocatalyst is its assistance in ultrafast pyrrole synthesis with no risk of metal contamination. Graphic abstract: [Figure not available: see fulltext.] Synopsis: A green and expeditious protocol for the synthesis of 2,5-dimethylpyrroles via combination of salicylic acid as catalyst (in its solid state) and microwaves has been introduced.

Amidosulfonic acid supported on graphitic carbon nitride: novel and straightforward catalyst for Paal–Knorr pyrrole reaction under mild conditions

A novel heterogeneous acidic catalyst was prepared by in situ immobilization of amidosulfonic acid (NH2SO3H) on graphitic carbon nitride (g-C3N4) under hydrothermal conditions. The textural morphology of NH2SO3H/g-C3N4 nanocomposite was characterized via powder X-ray diffraction, FT-IR, TGA, EDX, and scanning electron microscopy. The spatial arrangement of the amidosulfonic acid on the surface of g-C3N4 leads to the construction of a unique solid acid structure, resulting in a substantial enhancement of catalytic activity toward a high efficient preparation of pyrroles by Paal–Knorr reaction. The reactions undergo completion readily with good to excellent yields, with simple purification in an environmentally friendly manner. The NH2SO3H/g-C3N4 nanocomposite can be readily recycled, and no noteworthy reduction in the catalytic activity detected after four runs. Graphic abstract: [Figure not available: see fulltext.]

Naturally occurring organic acids for organocatalytic synthesis of pyrroles via Paal–Knorr reaction

Abstract: In this study, common naturally occurring organic acids, namely oxalic, malonic, succinic, tartaric and citric acid (as safe, inexpensive, and biodegradable organocatalysts), have been employed for Paal–Knorr pyrrole synthesis. The organocatalyzed reaction proved to be effective in ethanol at 60?°C. However, the reaction rate is mainly dominated by the nature and position of functional groups on the aromatic ring of substrate. This metal-free procedure tolerates a series of functional groups and should be considered as an asset to the pharmaceutical industry since no metal contamination could take place during the synthesis of pyrrole scaffolds. Graphic abstract: [Figure not available: see fulltext.].

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.

Synthesis, structure and in vitro anti-trypanosomal activity of non-toxic arylpyrrole-based chalcone derivatives

With an intention of identifying chalcone derivatives exhibiting anti-protozoal activity, a cohort of relatively unexplored arylpyrrole-based chalcone derivatives were synthesized in moderate to good yields. The resultant compounds were evaluated in vitro for their potential activity against a cultured Trypanosoma brucei brucei 427 strain. Several compounds displayed mostly modest in vitro anti-trypanosomal activity with compounds 10e and 10h emerging as active candidates with IC50 values of 4.09 and 5.11 μM, respectively. More importantly, a concomitant assessment of their activity against a human cervix adenocarcinoma (HeLa) cell line revealed that these compounds are non-toxic.

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.

Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles

A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C = N bond of the intermediate aldimine (aza-Favorsky reaction).

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.

Microwave-induced calcium(II) chloride-catalyzed Paal–Knorr pyrrole synthesis: a safe, expeditious, and sustainable protocol

Abstract: Among various alkali (Na, K) and alkaline-earth (Ca, Mg, Sr, Ba) chlorides, calcium(II) chloride was found to be a cost-effective Lewis acid catalyst for solvent-free synthesis of pyrroles from primary aromatic and aliphatic amines under open-vessel focused microwave irradiation. The salient features of this environmentally benign method are high to quantitative conversion, short reaction time, safe and clean reaction profile, possibility of scale-up to multigram quantities, and use of a low-cost, widely available, nontoxic catalyst.

Bio-based material as medium, mild and reusable catalyst for paal–knorr pyrrole synthesis with and without ultrasonic irradiation

Background: Pyrrole moiety is found in naturally occurring compounds such as chlorophyll, haem, and vitamin B12 and present in a number of drugs for example atorvastatin, ketorolac, elopiprazole, tolmetin and sunitinib. Various methods have been used for the synthesis of pyrrole derivatives; however, still there is a need for environmentally benign and economic protocol. Method: We have reported a simple, mild and speedy synthesis of N-substituted 2,5-dimethyl pyrrole derivatives in ‘’GAAS’’ as medium and catalyst at room temperature and under ultrasound irradiation. Results: This protocol was employed for the synthesis of various 2,5-dimethyl-N-substituted pyrrole-derivatives using both aliphatic as well as aromatic amines in short time (2 to 10 minutes)with excellent yield (84-95%) at room temperature and under ultrasonic irradiation. The catalytic system “GAAS’’ was regenerated and reused five times effectively without major loss of activity. Conclusion: In conclusion, we have developed an eco-friendly, simple, faster, reusable, mild, and efficient protocol for the synthesis of N-substituted pyrrole derivatives. This bio-based protocol is cost-effective and greener methodology for the synthesis of biologically active N-substituted pyrrole derivatives.