66302-37-2

Basic information

• Product Name: 2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole
• CAS NO: 66302-37-2
• Molecular Formula: C₂₁H₁₄ClNO
• Molecular Weight: 331.795
• Mol File: 66302-37-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 470.4°C at 760 mmHg
• Flash Point: 238.3°C
• Density: 1.214g/cm³
• Vapor Pressure: 1.44E-08mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole(66302-37-2)
• EPA Substance Registry System: 2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole(66302-37-2)

Safety Data

• Hazardous Substances Data: 66302-37-2(Hazardous Substances Data)

Usage

General Description

2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole, also known as Tris(diphenyl)oxazole or TDP, is a chemical compound with a molecular formula C22H16ClNO. It is a heterocyclic compound with a five-membered oxazole ring and has a chlorophenyl group attached at the second position. 2-(4-chlorophenyl)-4,5-diphenyl-1,3-oxazole has been studied for its potential use as a fluorescent probe for detecting metal ions and as a ligand for coordinating with metal ions in coordination chemistry. It has also been investigated for its potential use in organic light-emitting diodes (OLEDs) and as an intermediate in the synthesis of other pharmaceutical and agrochemical compounds. As a result of its diverse potential applications, research on this compound continues to be of interest in various scientific fields.

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Relevant articles and documents

Sonochemical synthesis of polyarylated oxazoles as potential cytotoxic agents

The ultrasound assisted facile, rapid and one-pot synthesis of 2-aryl substituted 4,5-diphenyloxazoles was achieved via the reaction of commercially available benzoin (or 2-hydroxy-2-phenylacetophenone) with benzylamines in the presence of IBX under mild conditions. The methodology involved initial IBX mediated conversion of benzoin to benzil and then reaction with benzylamine followed by intramolecular cyclization (C[sbnd]O bond formation) and finally aromatization in the presence of air in the same pot. The methodology afforded a variety of desired products that were assessed for their cytotoxic properties against a number of cancerous and a non-cancerous cell lines. Compounds 3h, 3n and 3o showed promising growth inhibition of these cell lines except the non-cancerous one and interactions with SIRT1 in silico as well as in vitro.

Lewis acid-mediated defluorinative [3+2] cycloaddition/aromatization cascade of 2,2-difluoroethanol systems with nitriles

The properties of C?F bonds, including high thermal and chemical stability, make derivatization of organic fluorine-containing compounds by the activation of the C?F bond and subsequent functionalization quite challenging. We herein report a Lewis acid-mediated defluorinative cycloaddition/aromatization cascade of 2,2-difluoroethanols with nitriles as a novel synthetic method for the preparation of 2,4,5-trisubstituted oxazoles. This reaction, which involves cleavage of two C?F bonds and the consecutive formation of C?O and C?N bonds in a one-pot fashion, features a broad substrate scope and moderate to high reaction yields. Mechanistic studies revealed that the reaction is initiated by the Lewis acid-mediated ring closure of the 2,2-difluoroethanol to produce the fluoroepoxide intermediate. (Figure presented.).

A convenient strategy to 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives through silver-mediated oxidative CO cross coupling/cyclization

This is a silver(I) mediated Cα(sp3)H activation of primary amines followed by oxidative CO cross coupling/cyclization for the construction of 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives. The protocol has been successfully utilized to synthesize the oxazole derivatives in good to excellent yields. In this oxidative coupling, the silver species after the reaction was successfully re-synthesized and reused with almost a similar activity.