20662-90-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-4-phenyloxazole is used as a building block for the synthesis of pharmaceuticals due to its potential pharmacological activities. It serves as a key component in the development of new drugs, contributing to the advancement of medicine.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Methyl-4-phenyloxazole is utilized as a building block in the synthesis of agrochemicals. Its incorporation into these products aids in the development of effective solutions for agricultural challenges.
Used as an Antimicrobial Agent:
2-Methyl-4-phenyloxazole is employed as an antimicrobial agent, leveraging its potential to combat various microorganisms. This application is crucial for both medical and environmental purposes, contributing to the control of infections and the preservation of health.
Used as a Ligand for Metal Ions:
2-Methyl-4-phenyloxazole also serves as a ligand for metal ions, playing a significant role in various chemical reactions and processes. Its ability to bind with metal ions allows for the creation of new compounds and materials with specific properties and applications.

InChI:InChI=1/C10H9NO/c1-8-11-10(7-12-8)9-5-3-2-4-6-9/h2-7H,1H3

Upstream product

• 60-35-5 acetamide 
• 70-11-1 α-bromoacetophenone 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 71022-74-7 (E)-1,2-diiodostyrene 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 177750-10-6 N-(1-(4-methoxy)phenylethyl)acetamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 536-74-3 phenylacetylene 
• 75-05-8 acetonitrile 
• 420-16-6 acetonitrile boron trifluoride complex 
• 1338062-05-7 4-methyl-N-[(2-propoxyphenyl)-λ³-iodanylidene]benzenesulfonamide 
• 1067-33-0 dibutyltin diacetate 
• 591-50-4 iodobenzene 
• 2248-46-6 ethyl 2,2-difluoro-2-phenylacetate 

Downstream Products

• 13739-48-5 2-methyl-4-phenyl-imidazole 
• 20662-93-5 5-bromo-2-methyl-4-phenyloxazole 
• 79965-75-6 2-methyl-4-(4-nitro-phenyl)-oxazole 
• 107-31-3 Methyl formate 
• 1575-95-7 N-acetylbenzamide 
• 117049-27-1 C₁₀H₉NO₃ 
• 100-47-0 benzonitrile 
• 2258-42-6 formyl acetic anhydride 
• 76162-88-4 2'-Methyl-6'-phenyl-[2,3']bipyridinyl-5'-ol 
• 76162-90-8 2-Methyl-6-phenyl-[3,4']bipyridinyl-5-ol 
• 85917-36-8 1-Phenyl-2-(4-phenyl-oxazol-2-yl)-ethanol 
• 133229-62-6 2-(5-hexenyl)-4-phenyloxazole 
• 65-85-0 benzoic acid 
• 293306-84-0 2-bromomethyl-5-bromo-4-phenyl oxazole 

Relevant academic research and scientific papers

Metal-Free [2+2+1] annulation of alkynes, nitriles and nitrogen atoms from iminoiodanes for synthesis of highly substituted imidazoles

Boron trifluoride nitrile complexes promote oxidative [2+2+1] annulations of alkynes, nitriles and N-atoms from iminoiodanes to give the corresponding 2,4-disubstituted and 2,4,5-trisubstituted N-tosylimidazoles in moderate to good yields with high regios

A novel synthetic method of 2,4-disubstituted oxazoles using carboxylic acid-derived Bu2Sn[OC(O)R]2

A novel synthetic method for the preparation of 2,4-disubstituted oxazoles was developed, entailing the reaction of dibutyltin diacylates Bu2Sn[OC(O)R]2 with 1-substituted acetylenes and TMSN3 to afford a range of 2,4-disu

PdII-Catalyzed Regio- and Enantioselective Oxidative C?H/C?H Cross-Coupling Reaction between Ferrocenes and Azoles

Asymmetric C?H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C?H/C?H cross-coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C?H bond cleavage of azoles is likely proceeding through a SEAr process and may not be a turnover limiting step.

Hypervalent iodane mediated reactions of: N -acetyl enamines for the synthesis of oxazoles and imidazoles

A hypervalent iodane reagent used for the intramolecular cyclization of N-acetyl enamines and intermolecular cyclocondensation of enamines and nitriles was investigated. The reaction was performed under mild conditions and gave oxazoles and imidazoles, respectively, in moderate to excellent yields. This transformation exhibits good reactivity, selectivity and functional group tolerance. The selectivity of the intra- or intermolecular reaction is dependent on the structure of N-acetyl enamines.

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.).

Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions

Aiming at the enhancement of electrophilicity of imino-λ3-iodanes, we have developed (tosylimino)pentafluorophenyl-λ3-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ3-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).

Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ3-iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl- λ3-iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ3-iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.

Synthesis of 2,4- and 2,4,5-substituted oxazoles via a silver triflate mediated cyclization

2,4- and 2,4,5-substituted oxazoles were prepared from a broad range of bromo-ketones and amides in high yield and purity.

Copper-catalyzed direct synthesis of iodoenamides from ketoximes

Iodide in copper's pathway: A new, efficient, and practical copper-catalyzed synthesis of Z-iodoenamides from readily available ketoximes has been developed (see scheme). The reaction was believed to proceed through a single-electron-transfer pathway. The corresponding Z-iodoenamides have been applied to the synthesis of substituted oxazoles, dienes, β-phenoxyl enamides, eneynes, β-acylenamides, and pyrroles (DCE=1,2-dichloroethane). Copyright