838-40-4

Basic information

• Product Name: 2,5-Diphenyl-1H-pyrrole
• Synonyms: 2,5-Diphenyl-1H-pyrrole;1H-Pyrrole, 2,5-diphenyl-
• CAS NO: 838-40-4
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.29
• Mol File: 838-40-4.mol
• Article Data: 53

Chemical Properties

• Boiling Point: 415.1°C at 760 mmHg
• Flash Point: 174.5°C
• Appearance: /
• Density: 1.105g/cm³
• Vapor Pressure: 1.02E-06mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 2,5-Diphenyl-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diphenyl-1H-pyrrole(838-40-4)
• EPA Substance Registry System: 2,5-Diphenyl-1H-pyrrole(838-40-4)

Safety Data

• Hazardous Substances Data: 838-40-4(Hazardous Substances Data)

Usage

Description

2,5-Diphenyl-1H-pyrrole is a heterocyclic aromatic compound with the molecular formula C16H13N. It features a pyrrole ring fused with two phenyl groups at the 2 and 5 positions, providing it with unique chemical properties and reactivity. 2,5-Diphenyl-1H-pyrrole is widely recognized for its potential bioactive properties, including anti-cancer and antimicrobial activities, and serves as a valuable building block in the synthesis of various organic compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
2,5-Diphenyl-1H-pyrrole is utilized as a key intermediate in the synthesis of pharmaceuticals for its unique chemical structure and reactivity. Its potential bioactive properties, such as anti-cancer and antimicrobial activities, make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2,5-Diphenyl-1H-pyrrole is employed as a valuable building block for the creation of various organic compounds. Its distinctive structure and reactivity allow for the formation of a wide range of molecules with diverse applications in different industries.
Used in Material Science:
2,5-Diphenyl-1H-pyrrole's unique chemical properties also make it suitable for use in material science. It can be incorporated into the development of new materials with specific properties, such as conductivity, stability, or reactivity, for applications in various fields, including electronics, energy, and environmental technologies.

InChI:InChI=1/C16H13N/c1-3-7-13(8-4-1)15-11-12-16(17-15)14-9-5-2-6-10-14/h1-12,17H

Upstream product

• 67421-66-3 2,5-diphenyl-1H-pyrrole-3-carbonitrile 
• 631-61-8 ammonium acetate 
• 495-71-6 phenacylacetophenone 
• 729-43-1 acetophenonazine 
• 16717-64-9 1-azidostyrene 
• 67-56-1 methanol 
• 68058-80-0 2,5-Diphenyl-3-diazopyrrole 
• 300-57-2 allylbenzene 
• 98-82-8 Isopropylbenzene 
• 64-19-7 acetic acid 
• 100-66-3 methoxybenzene 
• 121-69-7 N,N-dimethyl-aniline 
• 67-63-0 isopropyl alcohol 
• 108-88-3 toluene 

Downstream Products

• 206350-49-4 3-nitro-2,5-diphenyl-pyrrole 
• 110698-97-0 2,5-Diphenyl-3-formylpyrrole 
• 13220-01-4 (2,5-diphenyl-1H-pyrrol-3-yl)(phenyl)methanone 
• 109094-22-6 (2,5-diphenyl-pyrrol-3-ylmethyl)-dimethyl-amine 
• 75096-77-4 2,5-diphenyl-pyrrol-3-one oxime 
• 15969-46-7 2,6-diphenyl-3H-pyrimidin-4-one 
• 85814-61-5 1-(2,5-diphenyl-1H-pyrrol-3-yl)ethanone 
• 65297-99-6 (3,5-dimethyl-isoxazol-4-yl)-(2,5-diphenyl-pyrrol-3-yl)-methanone 
• 65298-00-2 (3,5-diphenyl-isoxazol-4-yl)-(2,5-diphenyl-pyrrol-3-yl)-methanone 
• 107268-20-2 C₂₈H₃₅N₃*2ClH 
• 107268-21-3 C₂₆H₃₁N₃O₂ 
• 107268-19-9 (4-Dimethylaminomethyl-2,5-diphenyl-1H-pyrrol-3-ylmethyl)-dimethyl-amine; hydrochloride 
• 107268-22-4 (2,5-Diphenyl-1H-pyrrol-3-ylmethyl)-diethyl-amine; hydrochloride 
• 107268-12-2 3-p-Chlorophenylazo-2,5-diphenylpyrrole 

Relevant articles and documents

P-Terphenyl as unexpected by-product in the synthesis of 2,5-diphenylpyrrole from acetophenone oxime and phenylacetylene

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Vinyl Azides as Radical Acceptors in the Vitamin B12-Catalyzed Synthesis of Unsymmetrical Ketones

Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under light irradiation vitamin B12 catalyzes the reaction of vinyl azides with electrophiles to afford unsymmetrical carbonyl compounds in decent yields. Mechanistic studies revealed that alkyl radicals are key intermediates in this transformation.

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.