22106-37-2

Basic information

• Product Name: 1-(4-PYRROL-1-YL-PHENYL)-ETHANONE
• Synonyms: AKOS B016275;1-(4-PYRROL-1-YL-PHENYL)-ETHANONE;1-[4-(1H-PYRROL-1-YL)PHENYL]-1-ETHANONE;ART-CHEM-BB B016275;1-[4-(1H-Pyrrol-1-yl)phenyl]ethanone;1-[4-(1-pyrrolyl)phenyl]ethanone;4'-(1-Pyrroyl)acetophenone
• CAS NO: 22106-37-2
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.22
• Mol File: 22106-37-2.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 320.8 °C at 760 mmHg
• Flash Point: 147.8 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 0.000311mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 1-(4-PYRROL-1-YL-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-PYRROL-1-YL-PHENYL)-ETHANONE(22106-37-2)
• EPA Substance Registry System: 1-(4-PYRROL-1-YL-PHENYL)-ETHANONE(22106-37-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 22106-37-2(Hazardous Substances Data)

Usage

General Description

1-(4-Pyrrol-1-yl-phenyl)-ethanone, also known as PPE, is a chemical compound with the molecular formula C12H11NO. It is a yellow crystalline solid that is commonly used in the production of pharmaceuticals and as a reagent in organic synthesis. PPE has been found to exhibit various biological activities, including anti-inflammatory and neuroprotective properties. It is also used as a building block in the synthesis of other organic compounds. However, PPE can be hazardous if not handled and stored properly, and caution should be exercised when working with this chemical.

InChI:InChI=1/C12H11NO/c1-10(14)11-4-6-12(7-5-11)13-8-2-3-9-13/h2-9H,1H3

Upstream product

• 109-97-7 pyrrole 
• 99-91-2 para-chloroacetophenone 
• 1019620-60-0 1-(4-(diallylamino)phenyl)ethane-1-one 
• 60259-40-7 C₁₂H₁₃NO 
• 99-92-3 p-aminobenzophenone 
• 6117-80-2 1,4-butenediol 
• 100-19-6 (4-nitrophenyl)ethanone 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 99-90-1 para-bromoacetophenone 
• 13329-40-3 4-Iodoacetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 1050196-63-8 (E)-3-(4-Chloro-phenyl)-1-(4-pyrrol-1-yl-phenyl)-propenone 
• 1251919-93-3 1-[4-(pyrrol-1-yl)phenyl]-3-(pyrrol-2-yl)prop-2-en-1-one 

Relevant articles and documents

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.

Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst

A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.