69640-32-0

Usage

Type of compound

Heterocyclic aromatic compound

Structural components

Pyrrole ring, 2-methoxyphenyl group

Versatile reactivity

Used in organic synthesis and pharmaceutical research

Potential pharmacological properties

Studied for its potential as a building block for the synthesis of novel organic molecules and in the development of new drug candidates

Applications

Materials science, dye intermediate in the chemical industry

Upstream product

• 116332-66-2 1-(2-Methoxyphenyl)-1,4-butandion 
• 250591-69-6 tert-butyl 2-(2-methoxyphenyl)-1H-pyrrole-1-carboxylate 
• 42041-50-9 2-(2-hydroxyphenyl)-1H-pyrrole 
• 74-88-4 methyl iodide 
• 74303-03-0 2-(2-benzyloxyphenyl)-1H-pyrrole 
• 5757-97-1 2-Methoxy-acetophenon-(dimethyl-hydrazon) 
• 606-45-1 2-methoxybenzoic acid methyl ester 
• 1198777-65-9 2-(2-methoxyphenyl)-1-(p-tolylsulfonyl)-2,3-dihydro-1H-pyrrole 
• 90-04-0 2-methoxy-phenylamine 
• 856438-60-3 4-(2-(benzyloxy)phenyl)-4-oxobutanal 
• 6609-56-9 2-methoxy-benzonitrile 
• 109-97-7 pyrrole 
• 578-57-4 2-bromoanisole 
• 100200-70-2 N-(2-methoxybenzylidene)-p-toluenesulfonamide 

Downstream Products

• 42041-50-9 2-(2-hydroxyphenyl)-1H-pyrrole 
• 1036204-58-6 C₂₉H₂₅IN₂O₂ 
• 1433119-06-2 C₂₉H₂₄N₂O₂ 
• 1332604-97-3 pentafluorophenyldipyrrinphenol 
• 1332605-05-6 C₂₉H₁₉F₅N₂O₂ 
• 1162652-12-1 C₃₂H₃₀N₂O₂ 
• 1374253-48-1 C₈₄H₇₈N₆O₆ 
• 1374253-42-5 C₃₂H₂₉BF₂N₂O₂ 
• 1162652-14-3 1,9-bis(2-hydroxyphenyl)-5-(phenyl)dipyrrin 

Relevant academic research and scientific papers

C–H Arylation of N-Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins

Herein, we are reporting metal-free conditions for radical initiation and direct C–H arylation of N-heteroarenes. Starting from aniline, the corresponding arenediazonium salt generated in situ is reduced to an aryl radical in the presence of chloropromazine hydrochloride, a new reagent for this application. The optimized procedures are mild, operationally simple, and are working successfully with more diverse substrates in comparison to reported methods. The optimized method is also employed for the synthesis of marine natural products Pentabromo- and Pentachloropseudilins (PBP/PCP). In the present study, we also validated the potential of the Pentachloropseudilin (PCP), thus synthesized, for inhibition of Myosin1 function in mammalian cells and confirmed that PCP phenocopies Myosin1c depletion in cells.

Cercosporin-bioinspired photoreductive activation of aryl halides under mild conditions

Bioinspired by the naturally-occurring cercosporin-driven infection process of plant pathogenic fungi Cercospora sp., here we took advantage of the photophysical properties of cercosporin, and used it as a metal-free photocatalyst to develop an unpreceden

Silver(I)-catalyzed route to pyrroles: Synthesis of halogenated pseudilins as allosteric inhibitors for myosin atpase and x-ray crystal structures of the protein-inhibitor complexes

The pentahalogenated 2-arylpyrrole-type alkaloids pentabromopseudilin and pentachloropseudilin represent a new class of isoform-specific allosteric inhibitors of myosin ATPase. Herein, we describe an application of the silver(I)-catalyzed cycloisomerizati

Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: A facile synthesis of 2-arylpyrroles

A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions. the Partner Organisations 2014.

Synthesis, solid-state analyses, and anion-binding properties of meso-aryldipyrrin-5,5′-diylbis(phenol) and -bis(aniline) ligands

The design of new molecular scaffolds for the selective recognition or transport of anions is often critical, because subtle changes in the substitution pattern may drastically impact the targeted properties. Herein, detailed spectroscopic and X-ray crystal-structure analyses were used to investigate the effect of the substitution pattern of a new series of N 2O2 or N4 anion sensors. Our study evidences two distinct in-in and in-out conformations depending on the nature of the substituent (e.g., phenol vs. aniline). Interestingly, because of intramolecular hydrogen bonds involving the -OH or the -NH2 functions, the dipyrrin subunit only acts as a scaffold and does not participate in the anion binding. Furthermore, the nature of the meso substituent was not critical, as similar binding affinities were measured for meso-C6H5 or meso-C6F5 ligands. Hence, the meso position can be further modified without any noticeable changes to the electron density on the dipyrromethene subunit.

Synthesis of pentabromopseudilin and other arylpyrrole derivatives via Heck arylations

Pentrabromopseudilin and other 2 and 3-arylpyrrole derivatives were synthesized through the Heck-Matsuda reaction involving endocyclic enecarbamates and N-protected 3-pyrrolines, respectively. The overall processes permitted an easy and efficient access t

Optimization of the Suzuki coupling reaction in the synthesis of 2-[(2-substituted)phenyl]pyrrole derivatives

A facile three-step synthesis of 2-(2-aminophenyl)pyrrole (1) and 2-[(2-aminomethyl)phenyl]pyrrole (2) is reported by use of Suzuki coupling of N-Boc-pyrrol-2-yl boronic acid (3) and o-substituted aryl halogenides, followed by hydrogenation. The Pd-catalyzed cross-coupling reaction is optimized to be applicable to a wide range of substitued aryl halogenides, with electron-donating and electron-withdrawing substituents, 5a-g. Moreover, Pd-catalyzed coupling of o-bromoaniline and 3 could be applied for the one-step preparation of pyrrolo[1,2-c]quinazolin-5(6H)-one (8). Copyright

Dipyrrinphenol-Mn(iii) complex: Synthesis, electrochemistry, spectroscopic characterisation and reactivity

Herein, we report the manganese complex with a novel trianionic ligand, the pentafluorophenyldipyrrinphenol ligand DPPH3. The X-ray crystal structure reveals that the MnIII complex exists in a dimeric form in the solid state. Electrochemical studies indicate two quasi-reversible one electron oxidation processes. EPR data on the one electron oxidised species in solution support the formation of a monuclear Mn complex with an S = 3/2 spin system. Preliminary studies towards epoxidation reactions were tested in the presence of iodosylbenzene (PhIO) and are in favour of an oxygen-atom-transfer (OAT) reaction catalyzed by the MnIII complex.

Triethanolamine-mediated palladium-catalyzed regioselective C-2 direct arylation of free NH-pyrroles

An atom-economical phosphane-free palladium-catalyzed direct C-2 arylation of unactivated free NH-pyrroles is devised. This method provides a straithforward route to a wide variety of substituted 2-aryl-1H-pyrroles from readily accessible starting materials. Iodoarenes bearing electron-withdrawing and electron-donating substituents are tolerated under the presented reaction conditions. The scope of the reaction is also expanded to N-aryl and -alkylpyrroles albeit in lower yields.

Alkoxy-substituted derivatives of π-conjugated acyclic anion receptors: Effects of substituted positions

The synthesis, solid-state assemblies, and anion binding affinities of π-conjugated acyclic anion receptors with alkoxyphenyl substituents are discussed. The position of the alkoxy moiety is essential to determining not only the electronic state but also the anion binding affinity. Copyright