110319-94-3

Usage

Derivative of pyrrole

Heterocyclic aromatic organic compound The compound is derived from pyrrole, which is a five-membered ring structure containing four carbon atoms and one nitrogen atom, giving it unique chemical and pharmacological properties.

4-fluorophenyl group

Modification of the pyrrole ring The addition of a 4-fluorophenyl group to the pyrrole ring contributes to the compound's unique properties and potential applications in medicinal chemistry.

Potential applications

Medicinal chemistry and pharmaceutical drug development 1H-Pyrrole,2-(4-fluorophenyl)-(9CI) has potential uses in the field of medicinal chemistry, particularly in the development of new pharmaceutical drugs.

Further study and exploration

Specific properties and potential uses The compound's unique properties and potential applications require additional research and investigation to fully understand and harness its potential in the field of medicinal chemistry.

Upstream product

• 329-79-3 1-(4-fluorophenyl)ethanone oxime 
• 74-86-2 acetylene 
• 109-97-7 pyrrole 
• 1765-93-1 4-fluoroboronic acid 
• 1868-08-2 bis(4-fluorophenyl)iodonium bromide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 22217-86-3 2-(4-fluorophenyl)-Δ¹-pyrrolidine 
• 904672-47-5 1-(4-fluorophenyl)but-3-en-1-one oxime 
• 1616603-22-5 C₁₂H₁₂FNO₂ 
• 61668-02-8 1-(4-fluorophenyl)but-3-en-1-one 
• 86718-78-7 1-(4-fluorophenyl)-3-buten-1-ol 
• 459-57-4 4-fluorobenzaldehyde 
• 116332-52-6 4-dimethylhydrazono-4-(4-fluorophenyl)butanaldimethylacetal 
• 116332-55-9 3-(1,3-dioxolan-2-yl)-1-(4-fluorophenyl)propan-1-one 

Downstream Products

• 115464-79-4 2-{4-[5-(4-Fluoro-phenyl)-1H-pyrrol-2-ylmethyl]-piperazin-1-yl}-ethanol 
• 110319-92-1 5-(4-fluorophenyl)-2-<<4-(2-methoxyphenyl)-1-piperazinyl>methyl>pyrrole 
• 110319-90-9 2-<<4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl>methyl>-5-(4-fluorophenyl)pyrrole 
• 1604834-02-7 C₂₂H₁₉FN₂O 
• 1392440-47-9 1-[5-(4-fluorophenyl)-1H-pyrrol-2-yl]ethan-1-one 

Relevant academic research and scientific papers

3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes: Synthesis, spectroscopic, electrochemical, and structural properties

This research was undertaken to obtain new 'BODIPY' dyes that fluoresce at relatively long wavelengths. The title compounds 1a-e were prepared via a divergent route involving Suzuki couplings of arylboronic acids to N-tert- butoxycarbonyl-4-bromopyrrole 2, condensation of the products with an acid chloride, and incorporation of the boron difluoride entity. Two alkyl- substituted systems 7a and 7b were also prepared for comparison; the critical difference between structures 1 and 7 is that the former have an aryl group attached to each pyrrole nucleus whereas the latter only have alkyl substituents on that same ring. UV absorption and fluorescence emission data were compared for compounds 1 and 7. Absorption and fluorescence emission maxima for compounds 1 occur at higher wavelengths than for compounds 7, and the Stokes shifts for the aryl-substituted compounds 1 are larger than for the alkyl-substituted compounds 7. Fluorescence quantum yields measured for compounds 1 are less than for compounds 7, and possible reasons for this are outlined. Other physical data for the compounds were also collected. Oxidation and reduction potentials of the systems were obtained from cyclic voltammetry experiments, and a single-crystal X-ray structure determination was performed for the bisnaphthyl-substituted compound 1b.

Synthesis of 3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes

2-Aryl pyrroles 2 were formed via Suzuki coupling of arylboronic acids to N-BOC protected 2-bromopyrrole. These pyrroles were used to produce 3,5-diaryl BODIPY dyes 1 having red-shifted fluorescence maxima relative to comparable alkyl-substituted systems. Absorption and fluorescence spectra of the compounds 1 are discussed.

Synthesis of 2-arylpyrroles via catalytic dehydrogenation of 2-aryl-1-pyrrolines in the presence of palladium-supported on alumina

A convenient synthesis of 2-arylpyrroles from the catalytic dehydrogenation of 2-aryl-1-pyrrolines in the presence of commercial palladium-supported on alumina (Pd/Al2O3) is described. The reaction scope was tested for aryl substituents with different steric hindrances and electronic natures. The dehydrogenation reaction conditions such as temperature, reflux time and amount of catalyst, revealed to be highly dependent on the 2-aryl substituent group, moderate to high yields and selectivities being obtained in a reaction involving straightforward work-up and purification procedures. In addition, the synthesis of the corresponding 2-aryl-1-pyrroline starting materials, through the cyclisation reaction involving 4-chlorobutyronitrile and aryl Grignard reagents, is also reported.

Isomer-Specific Hydrogen Bonding as a Design Principle for Bidirectionally Quantitative and Redshifted Hemithioindigo Photoswitches

A new class of bidirectionally quantitative photoswitches based on the hemithioindigo (HTI) scaffold is reported. Incorporation of a pyrrole hydrogen-bond donor leads to a bathochromic shift allowing for quantitative bidirectional isomerization. Additionally, extending conjugation from the electron-rich pyrrole results in quantitative visible-light photoswitches, as well as photoswitches that isomerize with red and near-infrared light. The presence of the hydrogen bond leading to the observed redshift is supported by computational and spectroscopic evidence.

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.

Direct arylation of arene and N -heteroarenes with diaryliodonium salts without the use of transition metal catalyst

A novel and simple transition metal-free direct arylation of arene and N-heteroarenes with diaryliodonium salts has been developed. This cross-coupling reaction is promoted only by base and gives the desired products in moderate to good yields.

Iron-mediated direct suzuki-miyaura reaction: A new method for the ortho -arylation of pyrrole and pyridine

(Figure presented) The first example of an iron-mediated direct Suzuki-Miyaura reaction between N-heterocyclic compounds and arylboronic acids is described, and both electron-rich and electron-deficient heteroarenes can be successfully used for the coupling reaction.

PYRROLES FROM KETOXIMES AND ACETYLENE. 44. METHYL ARYL KETOXIMES WITH REACTIVE SUBSTITUENTS

The Trofinov reaction was extended to methyl aryl ketoximes with substituents in the benzene ring that are unstable with respect to the action of a strongly basic medium.The corresponding pyrroles and their 1-vinyl derivatives were obtained. 4-Nitroacetophenone oxime, from which only 2-phenyl- and 1-phenyl-2-phenylpyrrole were obtained, and 4-bromoacetophenone oxime, the reaction of which leads to the formation of 1-vinyl-2-(4-vinyloxyphenyl)pyrrole in addition to the principal 2-(4-bromophenyl)pyrrole, constituted exceptions.

NEW METHODS FOR THE SYNTHESIS OF 2-ARYLPYRROLES

Two short and efficient synthetic approaches for -mostly unknown- 2-arylpyrroles are presented.The key intermediates 3 are conveniently obtained from commercially available acetophenones 5 (method I) or benzoic acid derivatives 10, 11 (method II).