107302-22-7

Usage

Uses

Used in Scientific Research:
1-(3-Bromophenyl)-1H-pyrrole is used as a chemical intermediate for the synthesis of more complex organic compounds. Its role in research is to facilitate the creation of new molecules with potential applications in various fields, such as pharmaceuticals, materials science, and chemical engineering. 1-(3-Bromophenyl)-1H-pyrrole's unique structure, which combines a pyrrole ring with a bromophenyl group, makes it a valuable building block for the development of novel molecules with specific properties and functions.

InChI:InChI=1/C10H8BrN/c11-9-4-3-5-10(8-9)12-6-1-2-7-12/h1-8H

Upstream product

• 109-97-7 pyrrole 
• 591-18-4 1-Bromo-3-iodobenzene 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 591-19-5 m-Bromoaniline 
• 526-99-8 meso-galactaric acid 

Downstream Products

• 634903-85-8 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[3-(1H-pyrrol-1-yl)phenyl]-1-benzothiophene-2-carboxamide hydrochloride 
• 1831152-32-9 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrrole 
• 635-90-5 1-phenylpyrrole 
• 53871-27-5 1-(3-fluorophenyl)-1H-pyrrole 
• 1450622-51-1 C₁₃H₁₅NO 
• 1450622-65-7 1-(3-(2-cyclohexylethyl)phenyl)-1H-pyrrole 
• 1417454-05-7 C₂₇H₃₄N₄O 
• 1368500-40-6 C₁₄H₁₇N₃ 
• 1417454-17-1 C₁₉H₂₅N₃O₂ 
• 185112-61-2 9-(3-bromophenyl)carbazole 
• 623905-24-8 2-(3-bromo-phenyl)-pyrrole 

Relevant academic research and scientific papers

L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction

l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.

A novel and convenient method for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones; synthesis and mechanistic study

An efficient, regioselective synthesis has been developed for the preparation of 5-(diphenylmethylene)-1H-pyrrol-2(5H)-ones from readily available 1H-pyrroles by sequential dibromination and selective organometallic bromine/lithium exchange followed by reaction with benzophenone. Comparison of various N-substituents was shown to demonstrate the high tolerance of the transformation to functional groups. The structures of the new products were determined by spectroscopic methods and confirmed by single-crystal X-ray diffraction measurement. In addition, theoretical study of the reaction mechanism and selective functionalization of the endocyclic double bond were also presented.

Identification of Noncompetitive Inhibitors of Cytosolic 5′-Nucleotidase II Using a Fragment-Based Approach

We used a combined approach based on fragment-based drug design (FBDD) and in silico methods to design potential inhibitors of the cytosolic 5′-nucleotidase II (cN-II), which has been recognized as an important therapeutic target in hematological cancers. Two subgroups of small compounds (including adenine and biaryl moieties) were identified as cN-II binders and a fragment growing strategy guided by molecular docking was considered. Five compounds induced a strong inhibition of the 5′-nucleotidase activity in vitro, and the most potent ones were characterized as noncompetitive inhibitors. Biological evaluation in cancer cell lines showed synergic effect with selected anticancer drugs. Structural studies using X-ray crystallography lead to the identification of new binding sites for two derivatives and of a new crystal form showing important domain swapping. Altogether, the strategy developed herein allowed identifying new original noncompetitive inhibitors against cN-II that act in a synergistic manner with well-known antitumoral agents.

Synthesis of heteroaromatic derivatives with nitrogen atoms: Tripyrrolyl pyrimidine and tripyrrolyl[1,3,5]triazine

As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1- yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.

A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water

A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.

Identification of a novel arylpiperazine scaffold for fatty acid amide hydrolase inhibition with improved drug disposition properties

We herein describe the systematic approach used to develop new analogues of compound 2, recently identified as a potent and selective fatty acid amide hydrolase (FAAH) inhibitor. Aiming at identifying new scaffolds endowed with improved drug disposition properties with respect to the phenylpyrrole-based lead, we subjected it to two different structural modification strategies. This process allowed the identification of derivatives 4b and 5c as potent, reversible and non-competitive FAAH inhibitors.

Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water

A simple and efficient copper-catalyzed method has been developed for N-arylations of nitrogen-containing heterocycles and aliphatic amines in water. The protocol uses (1E,2E)-oxalaldehyde dioxime (OADO) as the ligand, and water as the solvent, and shows good tolerance towards various functional groups.

Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles

Novel methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are governed by change of both the temperature and the solvent from tetrahydrofuran to diethyl ether. Regioselectiv

Synthesis and nuclear magnetic resonance spectroscopic studies of 1- arylpyrroles

A series of m- and p-substituted 1-phenyl, 1-benzyl, 1-benzoyl, and 1- (2-phenylethyl)pyrroles was prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of the β-H and the β-C of pyrroles [except 1-(2-phenylethyl)pyrroles] and the Hammettt σ. The observation may be explained in terms of the electronic effects of the substituents which are transmitted through bonds and through space by interaction of the p orbitals between β-Cs of the pyrrole ring and m- and p- Cs of the phenyl ring. Substituent constants of 1-pyrrolyl, 1-pyrrolylmethyl, and 1-pyrroloyl groups for the 1H and 13C chemical shifts of phenyl ring are also presented.

Reductive one batch synthesis of N-substituted pyrrolidines from primary amines and 2,5-dimethoxytetrahydrofuran

The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5- dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.