833-50-1

Usage

Uses

Used in Fluorescent Molecular Sensors:
2-Phenylbenzoxazole is used as a hydrophobic fluorophore in fluorescent molecular sensors, such as AS1-3. Its unique photophysical properties, including high fluorescence quantum yield and photostability, make it suitable for detecting and monitoring various analytes in biological and environmental systems.
Used in Chemical Synthesis:
2-Phenylbenzoxazole and its derivatives have been studied for their synthesis and potential applications in various fields. The synthesis of new series of 5-benzamidoand 5-phenylacetamido-substituted-2-phenylbenzoxazole derivatives has been investigated, which may lead to the development of new compounds with specific properties and uses.
Used in Microbiological Applications:
The microbiological activity of 2-Phenylbenzoxazole and its derivatives has been studied, indicating their potential use in antimicrobial applications. These compounds may exhibit inhibitory effects against certain microorganisms, making them useful in the development of new antimicrobial agents.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 12, p. 1135, 1964Chemistry Letters, 20, p. 1275, 1991Tetrahedron, 53, p. 457, 1997 DOI: 10.1016/S0040-4020(96)01009-5

InChI:InChI=1/C13H9NO/c1-2-6-10(7-3-1)13-14-11-8-4-5-9-12(11)15-13/h1-9H

Upstream product

• 85-44-9 phthalic anhydride 
• 95-55-6 2-amino-phenol 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 98-88-4 benzoyl chloride 
• 64-18-6 formic acid 
• 59986-60-6 (E)-o-hydroxybenzophenone oxime 
• 117-99-7 2-Hydroxybenzophenone 
• 132-60-5 cinchophen 
• 13787-59-2 3-benzoyl-2(3H)-benzoxazolone 
• 1020-39-9 N-(2-chlorophenyI)benzamide 
• 100-52-7 benzaldehyde 
• 51-19-4 2-aminophenol hydrochloride 
• 71-43-2 benzene 
• 100-47-0 benzonitrile 

Downstream Products

• 82593-17-7 (2-phenyl-5-benzoxazolyl)phenylmethanone 
• 23564-70-7 N-(o-Hydroxyphenol)benzamidine 
• 82461-25-4 2-phenylbenzoxazole dimer 
• 82461-24-3 9a,9b-Diphenyl-9a,9b-dihydro-9,10-dioxa-4b,4c-diaza-cyclobuta[1,2-a;4,3-a']diindene 
• 113990-49-1 N-(2-hydroxy-3-phenoxypropyl)-N-(2-benzoyloxy-3-phenoxypropyl)-o-hydroxyaniline 
• 226997-46-2 4-Benzooxazol-2-yl-benzenesulfonyl chloride 
• 95-55-6 2-amino-phenol 
• 65-85-0 benzoic acid 
• 3743-70-2 N-(2-hydroxyphenyl)benzamide 
• 1042719-77-6 2-([1,1′-biphenyl]-2-yl)benzo[d]oxazole 
• 1042719-78-7 2-(2,6-diphenylphenyl)-1,3-benzoxazole 
• 1042719-95-8 2-(4'-methyl-[1,1'-biphenyl]-2-yl)benzo[d]oxazole 
• 1042719-79-8 2-[2,6-di(4-methylphenyl)phenyl]-1,3-benzoxazole 
• 343978-73-4 (2-phenylbenzo[d]oxazole)₂Ir(μ-Cl)₂Ir(2-phenylbenzo[d]oxazole)₂ 

Relevant academic research and scientific papers

Mechanistic study of chemoselectivity in ni-catalyzed coupling reactions between azoles and aryl carboxylates

Itami et al. recently reported the C-O electrophile-controlled chemoselectivity of Ni-catalyzed coupling reactions between azoles and esters: the decarbonylative C-H coupling product was generated with the aryl ester substrates, while C-H/C-O coupling pro

A multistep flow process for the synthesis of highly functionalized benzoxazoles

An efficient and scalable transformation of 3-halo-N-acyl anilines to the corresponding benzoxazoles within a continuous flow reactor is reported. This transformation proceeds via base-mediated deprotonation, ortho-lithiation, and intramolecular cyclization to provide unstable lithiated benzoxazole moieties. The subsequent in-line electrophilic quench results in the formation of substituted benzoxazoles in high yield and quality. Continuous flow technology allowed for accurate temperature control and immediate in-line quench while minimizing the hold-up time for the unstable lithiated intermediates thereby minimizing associated byproduct formation.

Synthesis of 4-Alkenyl Benzoxazoles via Pd-catalyzed ortho C?H Functionalization of 2-Amidophenols

A one-pot direct transformation to remotely C?H alkene functionalized 2-aryl benzoxazoles from the reaction of amidophenol and electronically deficient olefin was reported. Control experiments confirm that the Pd-catalyzed regioselective C?H activation/alkenylation occurs at the first step by leading to ortho-alkenylated amidophenol; which subsequently underwent tandem intramolecular annulation to afford C4-alkenylated 2-arylbenzoxazole derivatives. (Figure presented.).

A key role for iodobenzene in the direct C-H bond functionalisation of benzoxazoles using PhI(OAc)2 mediated by a Pd(OAc) 2/1,10-phenanthroline catalyst system: In situ formation of well-defined Pd nanoparticles

PhI(OAc)2 has previously been reported as a reagent for the direct arylation of C-H bonds in benzoxazole in a PdII/IV-mediated process. However, evidence reported here suggests this reagent degrades to iodobenzene under the literature reported reaction conditions. Further, we present evidence for the rapid formation of Pd0 nanoparticles in this reaction, leading us to question what is the active catalytic Pd phase in coupling chemistry?.

Iron(III) Chloride Mediated para-Selective C-H Functionalization: Access to C5-Chloro and C5,C7-Dichloro/Dianisyl Substituted 2-Arylbenzoxazoles

Iron(III) chloride mediated para-selective C?H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole b

DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles

A novel DMF-assisted radical cyclization of o-isocyanodiaryl ethers via 1,5-aryl migration has been developed for the synthesis of a series of 2-arylbenzoxazoles by the FeCl3/TBHP/Et3N catalytic system in DMF. However, N,N-dimethylbenzo[d]thiazole-2-carboxamide and N,N-dimethylbenzo[d]selenazole-2-carboxamide were obtained from the corresponding substrate 2-isocyanophenyl p-methoxyphenyl thioether and 2-isocyanodiphenyl selenoether under the same conditions. A possible mechanism may involve aryl 1,5-migration and DMF-assisted radical cyclization of o-isocyanodiaryl ethers.

UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W-ZnO@NH2nanoparticles

Heterogeneous photocatalysts proffer a promising method to actualize eco-friendly and green organic transformations. Herein, a new photochemical-based methodology is disclosed in the preparation of a wide range of benzimidazoles through condensation of o-phenylenediamine with benzyl alcohols in the air under the illumination of an HP mercury lamp in the absence of any oxidizing species catalyzed by a new photocatalyst W-ZnO@NH2-CBB. In this photocatalyst, coomassie brilliant blue (CBB) is heterogenized onto W-ZnO@NH2 to improve the surface characteristics at the molecular level and enhance the photocatalytic activity of both W-ZnO@NH2 and CBB fragments. This unprecedented heterogeneous nanocatalyst is also identified by means of XRD, FT-IR, EDS, TGA-DTG, and SEM. The impact of some influencing parameters on the synthesis route and effects on the catalytic efficacy of W-ZnO@NH2-CBB are also assessed. The appropriate products are attained for both the electron-withdrawing and electron-donating substituents in the utilized aromatic alcohols. Furthermore, preparation of benzimidazoles is demonstrated to occur mainly via a radical mechanism, which shows that reactive species such as ·O2-, OH and h+ would be involved in the photocatalytic process. Stability and reusability studies also warrant good reproducibility of the nanophotocatalyst for at least five runs. Eventually, a hot filtration test proved that the nanohybrid photocatalyst is stable in the reaction medium. Using an inexpensive catalyst, UV-vis light energy and air, as a low cost and plentiful oxidant, puts this methodology in the green chemistry domain and energy-saving organic synthesis strategies. Finally, the anticancer activity of W-ZnO nanoparticles is investigated on MCF7 breast cancer cells by MTT assay. This experiment reveals that the mentioned nanoparticles have significant cytotoxicity towards the selected cell line.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation over metal-free BCN: effect of crystallinity and N-B pair exposure

Porous borocarbonitride (P-BCN), with the characteristics of enhanced crystallinity and improved N-B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Variouso-thio/hydroxy/aminoanilines and alcohols or toluenes could be converted to the corresponding 2-substituted benzothiazoles, benzoxazoles and benzimidazoles with good to excellent photocatalytic performance. The improved photocatalytic performance in comparison to bulk BCN should be due to the crystallinity-enhancement-induced improvement in charge separation and transmission. The increased N-B pair exposure promoted superoxide radical generation due to the electron-enriched N atoms, as well as improved oxidation ability due to the valence band constructed by the B 2p orbital. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicalsviametal-free heterogeneous photocatalysis.

Heterocyclic reaction inducted by Br?nsted–Lewis dual acidic Hf-MOF under microwave irradiation

Use of green chemistry and alternative strategies has been explored to prepare diverse organic derivatives. The combination between heterogeneous catalyst, environmentally benign reaction and high-yielding methods is gaining momentum. Herein, a defective 6-connected Hf-MOF, named Hf-BTC, was efficiently synthesized and characterized for the heterogeneous catalysis under microwave irradiation. The MOF features including structural defect, porosity, acidity, and stability was analyzed by powder X-ray diffraction, N2 sorption isotherms, acid-base titration, and thermal gravimetric analysis. In the catalytic studies, the Br?nsted-Lewis dual acidic Hf-BTC was efficiently applied for the synthesis of the heterocyclic compounds via the microwave-assisted cycloaddition and condensation reactions. The reactions proceeded smoothly in the presence of the Hf-MOF with a broad scope of substrates provided the expected products in high to excellent yields (up to 99 %) for few minutes and the catalyst could be easily recycle over many consecutive reactions without loss of its reactivity and structure.