23351-09-9

Usage

Chemical Properties

light yellow to beige crystalline powder

InChI:InChI=1/C10H9NO/c12-10-5-3-9(4-6-10)11-7-1-2-8-11/h1-8,12H

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 123-30-8 4-amino-phenol 
• 109-97-7 pyrrole 
• 106-41-2 4-bromo-phenol 
• 100-02-7 4-nitro-phenol 
• 5145-71-1 1-(p-methoxyphenyl)pyrrole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 81329-31-9 1-(4-fluorophenyl)-1H-pyrrole 
• 540-38-5 p-Iodophenol 
• 51-78-5 p-aminophenol hydrochloride 
• 92636-36-7 1-(4-iodophenyl)pyrrole 
• 5044-38-2 1-(4-chlorophenyl)-1H-pyrrole 

Downstream Products

• 548764-08-5 methyl-phenyl-carbamic acid 4-pyrrol-1-yl-phenyl ester 
• 1011481-53-0 4-(1H-pyrrol-1-yl)phenyl methanesulfonate 
• 1005736-95-7 (R)-2-(4-Pyrrol-1-yl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Discovery of target based novel pyrrolyl phenoxy derivatives as antimycobacterial agents: An in silico approach

A new series of pyrrolyl phenoxy derivatives bearing alkoxy linker were synthesized and evaluated for anti-tubercular activity (anti-TB) against Mycobacterium tuberculosis. Molecular modeling, pharmacophore constructed using GALAHAD to produce an effective alignment of data set and evaluated by Pareto ranking. The pharmacophore features were filtered by Surflex-dock study using enoyl ACP reductase from M. tuberculosis, which is one of the key enzymes involved in type II fatty acid biosynthesis pathway of M. tuberculosis. Compound 6a27 showed the H-bond with NAD+, whereas compound 6a26 showed H-bonds with Tyr158, Thr196, Met199 and NAD+ that fitted well into the binding pocket of target InhA. The alkoxy linker bridge and acceptor groups with benzene ring were advantageous for anti-TB activity, which merit further investigation.

A Novel N-Substituted Pyrrole Based Surface Modification for Biosensing

Immobilization of proteins, mostly antigens, antibodies or enzymes on a solid surface, is one of the most important steps in the development of every biosensor. Different chemical methods as well as site-directed strategies have been developed in order to obtain highest functionality and stability for the sensoric device. In the present work, a novel method for the immobilization of biomolecules on a surface plasmon resonance (SPR) device is described. New N-substituted pyrroles are synthesized and deposited on a gold surface using electrochemical polymerization. To evaluate the established four different surfaces, the binding behavior between a fusion protein consisting of the lectin concanavalin A (ConA) as well as streptavidin (Sav) binding domains and the sugar mannan, which has been chemically coupled to the poly-pyrrole (PPy) surface is investigated. A pyrrole-N-C16/pyrrole co-polymer surface as well as a pyrrol-1-yl hexanoic acid/pyrrole (PHCP) surface give best results.

A solvent-free manganese(II) -catalyzed Clauson-Kaas protocol for the synthesis of N-aryl pyrroles under microwave irradiation

The first manganese-catalyzed modified Clauson-Kaas reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20?min). The above qualities attest to the green nature of this reaction.

Cobalt-Catalyzed Defluorosilylation of Aryl Fluorides via Grignard Reagent Formation

Transition-metal-catalyzed transformations of the carbon-fluorine bond not only tackle an interesting problem of challenging bond activation but also offer new synthetic strategies where the relatively inert C-F bond is converted to versatile functional groups. Herein we report a practical cobalt-catalyzed silylation of aryl fluorides that uses a cheap electrophilic silicon source with magnesium. This method is compatible with various silicon sources and can be operated under aerobic conditions. Mechanistic studies support the in situ formation of a Grignard reagent, which is captured by the electrophilic silicon source.

Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides

Developing efficient and selective strategies to approach complex architectures containing (multi)stereogenic centers has been a long-standing synthetic challenge in both academia and industry. Catalytic cascade reactions represent a powerful means of rapidly leveraging molecular complexity from simple feedstocks. Unfortunately, carrying out cascade Heck-type reactions involving unactivated (tertiary) alkyl halides remains an unmet challenge owing to unavoidable β-hydride elimination. Herein, we show that a modular, practical, and general palladium-catalyzed, radical three-component coupling can indeed overcome the aforementioned limitations through an interrupted Heck/allylic substitution sequence mediated by visible light. Selective 1,4-difunctionalization of unactivated 1,3-dienes, such as butadiene, has been achieved by employing different commercially available nitrogen-, oxygen-, sulfur-, or carbon-based nucleophiles and unactivated alkyl bromides (>130 examples, mostly >95:5 E/Z, >20:1 rr). Sequential C(sp3)-C(sp3) and C-X (N, O, S) bonds have been constructed efficiently with a broad scope and high functional group tolerance. The flexibility and versatility of the strategy have been illustrated in a gram-scale reaction and streamlined syntheses of complex ether, sulfone, and tertiary amine products, some of which would be difficult to access via currently established methods.

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions

The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).

ZnAl2O4–Bi2O3 composite nano-powder as an efficient catalyst for the multi-component, one-pot, aqueous media preparation of novel 4H-chromene-3-carbonitriles

Abstract: A composite structure of ZnAl2O4–Bi2O3 nanopowder was prepared from the reaction of a watery solution of Zn(NO3)2, Al(NO3)3, and Bi(NO3)3 with a dilute solution of amino ethanol in water via a simple precipitation-complexation method. The as-prepared composite was used for the one-pot synthesis of 2-amino-4-aryl-7-(pyrrolidin-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-7-(piperidin-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-7-(1H-pyrrol-1-yl)-4H-chromene-3-carbonitrile, 2-amino-4-aryl-6-(2-(piperidin-1-yl)ethyl)-4H-chromene-3-carbonitrile and 2-amino-4-aryl-6-(1H-pyrrol-1-yl)-4H-chromene-3-carbonitrile derivatives. This procedure is very simple and affords excellent yields. Graphical Abstract: [Figure not available: see fulltext.]

N-terminal strategy (N1-N4) toward high performance liquid crystal materials

Liquid crystal materials have a variety of applications in many fields such as display techniques as well as photonics and optics. However, only few design principles have been disclosed on liquid crystal materials with different N-heterocycles as the terminal groups, which hinder the development of the heterocyclic liquid crystals. Here, a strategy of molecular design for N-heterocyclic liquid crystal materials is reported. On the basis of this strategy, a series of convenient N-heterocycles such as pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole were applied to synthesize the novel liquid crystals. Most of them have proved to exhibit good mesomorphic behaviors which make them excellent components in the mixture of the LCDs materials. The simple attachment of N-heterocyclic units to the liquid crystal molecules through a mild reaction condition will provide a good prospect for the design of N-heterocyclic liquid crystals.

Functionalized multi-walled carbon nanotubes as an efficient reusable heterogeneous catalyst for green synthesis of N-substituted pyrroles in water

In this protocol, the functionalization of multi-walled carbon nanotubes (MWCNTs) was carried out and the resulting sulfonated MWCNTs were characterized by FT-IR, XRD, SEM, BET, EDX, XPS and Raman spectroscopy that are each discussed separately in the text. Then, the MWCNT-SO3H composite was applied as an efficient, recyclable heterogeneous catalyst for the synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxy tetrahydrofuran with primary amines under clean and mild conditions. In this reaction, the N-substituted pyrroles were obtained as beneficial and significant products in short reaction times (30-65 min) and good to excellent yields (40-92%) with high purity. The products were obtained through a simple work up procedure and characterized by FT-IR, 1H NMR and 13C NMR. After the end of the reaction, the nanocatalyst was recovered and reused several times without efficient loss of its activity for the preparation of N-substituted pyrroles.

Nano sulfated titania as a heterogeneous solid acid catalyst for the synthesis of pyrroles by clauson-kaas condensation under solvent-free conditions

A new and environmentally benign method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-dimethoxytetrahydrofuran with amines and diamines in the presence of nano sulfated titania under solvent-free conditions is presented. This new protocol features simple operation, easy availability, stability, and eco-friendliness of catalyst, as well as high to excellent yields of products. In addition, we report for the first time an alternative method for the synthesis of pyrroles from aromatic amines containing the β-lactam fragment using nano sulfated titania as catalyst.