7420-86-2

Usage

Uses

Used in Analytical Chemistry:
5-methyl-2-phenylbenzoxazole is used as a fluorescence probe for detecting and analyzing various chemical and biological substances. Its fluorescent properties allow for sensitive and selective detection, making it a valuable tool in analytical chemistry.
Used in Biochemistry:
In the field of biochemistry, 5-methyl-2-phenylbenzoxazole is employed as a fluorescent marker for studying the structure, function, and interactions of biomolecules such as proteins and nucleic acids. Its ability to label and visualize biomolecules aids in understanding their roles in biological processes.
Used in Materials Science:
5-methyl-2-phenylbenzoxazole is utilized in the development of advanced materials with unique optical, electronic, and sensing properties. Its incorporation into materials can enhance their performance and enable new applications in areas such as optoelectronics, sensors, and imaging.
Used in Organic Synthesis:
5-methyl-2-phenylbenzoxazole is used as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique structural and chemical properties make it a versatile building block for creating new molecules with potential applications in medicine, agriculture, and other fields.
Used in Pharmaceutical Research:
5-methyl-2-phenylbenzoxazole has been studied for its potential biological activities and pharmacological effects. Its exploration in drug discovery and development could lead to the creation of new therapeutic agents with novel mechanisms of action.

InChI:InChI=1/C14H11NO/c1-10-7-8-13-12(9-10)15-14(16-13)11-5-3-2-4-6-11/h2-9H,1H3

Upstream product

• 110-86-1 pyridine 
• 64712-30-7 2-hydroxy-5-methylbenzophenone (E) oxime 
• 98-09-9 benzenesulfonyl chloride 
• 64-17-5 ethanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 75-36-5 acetyl chloride 
• 93-63-0 2-benzoylamino-4-methyl-phenol 
• 19430-24-1 4-methyl-2-[(phenylmethylene)amino]phenol 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 452-84-6 3-amino-4-fluorotoluene 
• 878193-80-7 (E)-2-(benzylideneamino)-4-methylphenol 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 95-84-1 3-amino-4-hydroxytoluene 
• 65-85-0 benzoic acid 
• 35875-76-4 5-methyl-2-(2-hydroxyphenyl)benzoxazole 
• 54785-43-2 5-bromomethyl-2-phenyl-benzooxazole 

Relevant academic research and scientific papers

Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime

A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.

Dowex 50W: A green mild reusable catalyst for the synthesis of 2-aryl benzoxazole derivatives in aqueous medium

In this work simple efficient, one pot and environmentally friendly method was developed for the synthesis of 2-Aryl-1H-benzoxazole derivatives at 80oC using ortho-aminophenol and various aldehydes. It has been found that Dowex 50W is an effective catalyst to prepare moderate to high yield of a variety of benzoxazole derivatives through a clean and simple process. Aqueous medium, green methodology, rapid reaction, reusability of heterogeneous catalyst are the great advantages of this protocol.

Stable Pd(0) Complexes with Ferrocene Bisphosphanes Bearing Phosphatrioxaadamantyl Substituents Efficiently Catalyze Selective C-H Arylation of Benzoxazoles by Aryl Chlorides

Versatile applications and unique performance of 1,1’-bis(diphenylphosphanyl)ferrocene (dppf) in coordination chemistry and catalysis prompted the search for its analogs. This contribution describes the synthesis of the first donor-unsymmetric dppf congeners bearing bulky and rigid 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantyl (CgP) donor groups, viz. Ph2PfcPCg (1) and Ph2PfcCH2PCg (2; fc=ferrocene-1,1’-diyl). Bis-phosphanes 1 and 2 were converted into air-stable Pd(0) complexes, [Pd(ma)(L^L)] (L^L=1 and 2; ma=maleic anhydride). Together with [Pd(ma)(dppf)], these complexes were applied as catalysts in Pd-catalyzed C?H arylation of benzoxazoles with aryl chlorides in n-butanol as an environmentally benign solvent. Among all catalysts tested in this study, complex [Pd(ma)(2)] performed the best, providing a high-yield and selective synthesis of 2-arylbenzoxazoles from a range of the generally less reactive chloroarenes at low catalyst loading (typically 1 mol.%). Under similar conditions, the structurally related heterocycles (e. g., 1-methylbenzimidazole and benzothiazole) did not react.

TEMPO-mediated aerobic oxidative synthesis of 2-aryl benzoxazoles via ring-opening of benzoxazoles with benzylamines

A simple and efficient TEMPO-mediated system for aerobic oxidative synthesis of 2-aryl benzoxazoles from readily available benzoxazoles and primary benzylic and hetero benzylic amines is presented in one pot. The reaction proceeds through the ring-opening of benzoxazoles and is followed by oxidative condensation with benzylamines. These metal-free, straightforward reactions worked well with a wide range of substrates, yielding moderate to good yields under mild conditions using air as an external green oxidant.

One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.

Synthetic method 2 -aryl benzoxazole derivative (by machine translation)

The invention discloses a synthesis method of 2 -aryl benzoxazole derivative, which comprises the following steps: reacting o-nitrophenol derivative with an aryl formaldehyde derivative in the presence of a pyridine accelerant and an elemental sulfur reducing agent to obtain 2 -arylbenzoxazole derivative. (by machine translation)

One-pot multicomponent reaction of catechols, ammonium acetate, and aldehydes for the synthesis of benzoxazole derivatives using the fe(iii)-salen complex

The Fe(III)-salen complex has been applied successfully as a catalyst for the novel, simple, efficient, and one-pot multicomponent synthesis of benzoxazole derivatives from catechols, ammonium acetate as the nitrogen source, and aldehydes (nontoxic and cheap alternatives of amines) for the first time. Using this procedure, a wide range of benzoxazoles was successfully synthesized in the presence of a catalyst in EtOH under mild conditions, and all products were obtained in excellent yields. To the best of our knowledge, this method is the first example of the multicomponent synthesis of benzoxazole derivatives using these starting materials. The notable features such as the use of air that is considered as a benign oxidant and EtOH as a green solvent, ease of product separation, readily available and inexpensive aldehydes, and mild conditions make our procedure more efficient and practical for organic synthesis. Moreover, the current protocol is successfully applied to synthesize desirable products on a large scale.

Visible Light-Induced Copper-Catalyzed C—H Arylation of Benzoxazoles?

A general method for visible light-induced copper-catalyzed arylation of sp2 C—H bonds of azoles has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide as base. A variety of azoles including benzooxazole and benzothiazole can be arylated. Furthermore, electron-poor heterocycles such as thiophene possessing one electron-withdrawing group can also be arylated.

Straightforward synthesis of benzoxazoles and benzothiazoles via photocatalytic radical cyclization of 2-substituted anilines with aldehydes

Eosin Y-catalyzed one-pot coupling and cyclization of o-substituted anilines with aldehydes to form benzoxazoles and benzothiazoles under mild condition has been developed. The reaction scope was broadly tolerant of various 2-substituted anilines and aldehydes. The desired products were obtained in high yields with the use of eosin Y as a photocatalyst under a substantial refinement of reaction conditions in comparison with previous literature. Based on the experimental results observed, a plausible mechanism involving a radical process has been proposed.

Sulfur-Promoted Synthesis of Benzoxazoles from 2-Aminophenols and Aldehydes

Elemental sulfur (S8) was found to be an excellent stoichiometric oxidant to promote oxidative condensation of 2-aminophenols with a wide range of aldehydes, including aliphatic aldehyde such as cyclohexanecarboxaldehyde. The reactions were catalyzed by sodium sulfide in the presence of DMSO as an additive. The benzoxazole products were obtained in satisfactory yields. The reaction conditions could be applied to larger syntheses (10–50 mmol).