28687-81-2

Basic information

• Product Name: 5(4H)-Oxazolone, 2,4-diphenyl-
• Synonyms: 5(4H)-Oxazolone, 2,4-diphenyl-;2,4-Diphenyl-2-oxazolin-5-one;Azlactone;2,4-diphenyl-1,3-oxazol-5(4h)-one;2,4-diphenyl-4H-1,3-oxazol-5-one
• CAS NO: 28687-81-2
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• Mol File: 28687-81-2.mol

Chemical Properties

• Melting Point: 100 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 368.5°Cat760mmHg
• Flash Point: 169.2°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 1.26E-05mmHg at 25°C
• Refractive Index: 1.621
• PKA: 1.78±0.40(Predicted)
• CAS DataBase Reference: 5(4H)-Oxazolone, 2,4-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(4H)-Oxazolone, 2,4-diphenyl-(28687-81-2)
• EPA Substance Registry System: 5(4H)-Oxazolone, 2,4-diphenyl-(28687-81-2)

Safety Data

• Hazardous Substances Data: 28687-81-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
5(4H)-Oxazolone, 2,4-diphenylis used as a key intermediate in the synthesis of various pharmaceutical and agrochemical products. Its unique structure and reactivity allow for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Organic Synthesis:
As a building block in organic synthesis, 5(4H)-Oxazolone, 2,4-diphenylis employed for the preparation of complex molecules with potential biological activities. Its versatility in forming different chemical bonds and its compatibility with various synthetic routes make it a valuable component in the creation of novel compounds.
Used in Optoelectronic Devices:
5(4H)-Oxazolone, 2,4-diphenylhas been studied for its potential as a material for optoelectronic devices. Its electronic properties and compatibility with other materials make it a promising candidate for applications in light-emitting diodes, solar cells, and other optoelectronic technologies.
Used in Organic Semiconductors:
In the field of organic semiconductors, 5(4H)-Oxazolone, 2,4-diphenylis considered for its potential use in the development of organic thin-film transistors, organic light-emitting diodes, and other electronic devices. Its electronic properties and processability contribute to the advancement of flexible and cost-effective electronic components.

InChI:InChI=1/C15H11NO2/c17-15-13(11-7-3-1-4-8-11)16-14(18-15)12-9-5-2-6-10-12/h1-10,13H

Upstream product

• 98-88-4 benzoyl chloride 
• 29670-63-1 N-benzoyl-2-phenylglycine 

Downstream Products

• 111796-60-2 2,4-diphenyl-5-(pyridin-3-yl)oxazole 
• 91527-88-7 2,4-Diphenyl-4-[3-(tetrahydro-pyran-2-yloxy)-propyl]-4H-oxazol-5-one 
• 98767-85-2 N-(1-Methyl-2-oxo-3-phenyl-4-thiophen-2-yl-azetidin-3-yl)-benzamide 
• 719263-73-7 2,4-diphenyl-4H-oxazol-5-one 
• 719263-73-7 2,4-diphenyl-4H-oxazol-5-one 
• 91527-78-5 N-(2-Oxo-3-phenyl-tetrahydro-furan-3-yl)-benzamide 
• 91527-79-6 N-(2-Oxo-3-phenyl-tetrahydro-pyran-3-yl)-benzamide 
• 91527-81-0 N-(1-Dimethylcarbamoyl-3-hydroxy-1-phenyl-propyl)-benzamide 
• 91527-82-1 N-(1-Dimethylcarbamoyl-4-hydroxy-1-phenyl-butyl)-benzamide 
• 91527-80-9 N-(2-Oxo-3-phenyl-oxacyclopentadec-3-yl)-benzamide 
• 91527-84-3 N-[1-Dimethylcarbamoyl-1-phenyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-benzamide 
• 91527-83-2 N-(1-Dimethylcarbamoyl-13-hydroxy-1-phenyl-tridecyl)-benzamide 
• 91527-85-4 N-[1-Dimethylcarbamoyl-1-phenyl-4-(tetrahydro-pyran-2-yloxy)-butyl]-benzamide 

Relevant articles and documents

Enantioselective iridium catalyzed α-alkylation of azlactones by a tandem asymmetric allylic alkylation/aza-Cope rearrangement

The development of an iridium catalyzed enantioselective α-alkylation of azlactones has been described. The reaction provides rapid access to a wide range of enantio-enriched quaternary carbon center allylated 2,4-diaryloxazol-5(2H)-ones in excellent yiel

Catalyst-free synthesis of N -(1,7-dioxotetrahydropyrazolo[1,2-a]pyrazol-2- yl)benzamide derivatives by 1,3-dipolar cycloaddition and rearrangement

N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)-benzamide derivatives, a novel class of compounds, were synthesized by 1,3-dipolar cycloaddition of azomethine imines with azlactones and subsequent rearrangement. The reaction can be completed rapidly under mild conditions without a catalyst. Georg Thieme Verlag Stuttgart New York.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Alkynyliodonium salt mediated alkynylation of azlactones: Fast access to Cα-tetrasubstituted α-amino acid derivatives

An efficient electrophilic alkynylation of azlactones (oxazol-5(4H)-ones) is developed using alkynyl(phenyl)iodonium salts as the electrophilic alkyne source. After remarkably short reaction times, the desired alkyne functionalized azlactones are obtained in 60-97% yield and can be transformed easily into a variety of quaternary α-amino acid derivatives.

Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition

Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole- 4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Inhibition of the human proteasome by imidazoline scaffolds

The proteasome has emerged as the primary target for the treatment of multiple myeloma. Unfortunately, nearly all patients develop resistance to competitive-type proteasome inhibitors such as bortezomib. Herein, we describe the optimization of noncompetit

One-pot synthesis of 2,4,5-trisubstituted oxazoles from N-acyl amino acids by a combination of cyclodehydration with N,N′-diisopropylcarbodiimide and Wittig olefination

By a combination of cyclodehydration of N-acyl amino acids with N,N′-diisopropylcarbodiimide (DIC) and non-classical Wittig olefination of the resultant 5(4H)-oxazolones with Ph3PCHCN and Ph 3PCHCOOEt, 5-oxazoleacetonitriles and 5-oxazoleacetates were synthesized in one-pot in 41-85% and 57-70% yields, respectively.

Dynamic kinetic resolution of azlactones catalyzed by chiral Bronsted acids

Chiral Bronsted acids have been shown for the first time to catalyze the dynamic kinetic resolution of azlactones. 3,3'-Bis-(9-anthryl)-BINOL phosphoric acid 3c is particularly effective in the case of 4-aryl-substituted substrates, producing 85-92% ee's.

Application of a novel [3+2] cycloaddition reaction to prepare substituted imidazoles and their use in the design of potent DFG-out allosteric B-Raf inhibitors

B-Raf protein kinase, which is a key signaling molecule in the RAS-RAF-MEK-ERK signaling pathway, plays an important role in many cancers. The B-Raf V600E mutation represents the most frequent oncogenic kinase mutation known and is responsible for increas

Structural-activity relationship study of highly-functionalized imidazolines as potent inhibitors of nuclear transcription factor-κB mediated IL-6 production

We herein describe the synthesis and anti-inflammatory properties of a small library of imidazoline-based NF-κB inhibitors. The structure-activity relationship of various substituents on an imidazoline core structure was evaluated for the ability to inhibit NF-κB mediated IL-6 production. Optimization of the scaffolds was pursued by correlating luciferase-based NF-κB reporter assays with inhibition of IL-6 production in IL-1β stimulated human blood. Several derivatives were found to inhibit NF-κB mediated IL-6 production in the nanomolar range in IL-1β stimulated human blood.