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 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 91718-58-0 benzoic acid-(2-amino-phenyl ester); hydrochloride 
• 132-60-5 cinchophen 
• 13787-59-2 3-benzoyl-2(3H)-benzoxazolone 
• 1020-39-9 N-(2-chlorophenyI)benzamide 
• 1624-53-9 2-(benzylideneamino)phenol 

Downstream Products

• 61372-51-8 N-methyl-2-phenyl-benzoxazolium iodide 
• 3164-28-1 6-nitro-2-phenylbenzo[d]oxazole 
• 3743-70-2 N-(2-hydroxyphenyl)benzamide 
• 62164-85-6 5,6-dinitro-2-phenyl-benzooxazole 
• 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 
• 226997-46-2 4-Benzooxazol-2-yl-benzenesulfonyl chloride 
• 95-55-6 2-amino-phenol 
• 65-85-0 benzoic acid 
• 24978-46-9 3-(benzoxazol-2-yl)benzene-1,2-diol 
• 13316-89-7 benzoic acid-(2-hydroxy-3,5-dinitro-anilide) 
• 53421-88-8 2-phenyl-1,3-benzoxazol-6-ylamine 

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.

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.

Novel and efficient heterogeneous polymer supported copper catalyst for synthesis of 2-substituted Benzoxazoles from 2-Haloanilides

A novel polymer supported copper complex is prepared by the immobilization of copper iodide on chemically modified polyacrylonitrile and its application in heterogeneous catalysis is described. The catalyst was prepared by easy method via synthetic modification of Polyacrylonitrile (PAN) using ethylene diamine followed by the complexation with CuI. After characterization, this complex was explored as a green and efficient heterogeneous catalyst for the synthesis of 2-benzoxazoles from 2-haloanilides. The reaction was performed without adding additional ligand and the catalyst shows activity over a broad range of substrates with quantitative product yields. The catalyst was easily recovered by simple filtration and reused successfully for further cycle.

Investigation of Pd-PEPPSI catalysts and coupling partners towards direct C2-arylation/heteroarylation of benzoxazole

2-Aryl/heteroaryl-substituted benzoxazoles are important heterocyclic motifs extensively found in several bioactive molecules, pharmaceuticals and natural products. In view of the importance of these compounds, there is need to develop easiest and simplest synthetic routes. The motive of this current work is to conduct the direct C2-arylation reaction on benzoxazole with various cross-coupling partners like aryl/heteroaryl halide/carboxylic acid/diazonium tetrafluoroborate/sulfonyl chloride/boronic acids in the presence of different symmetrical and unsymmetrical Pd-PEPPSI (pyridine-enhanced pre-catalyst preparation by stabilization initiation) catalysts via C (sp2)–C (sp2) bond formation. Compared with other coupling partners, boronic acids coupled with benzoxazole very efficiently in the presence of sterically and electronically tunable bulky1,3-bis(N,N′-2,4,6-triisopropylbenzyl)benzimidazolium-Pd-PEPPSI complex in open air to offer the corresponding C2-aryl/heteroaryl benzoxazole compounds. Further, it is worthy to mention that there is no need of any external oxidant/ligand/additive for the complete conversion of starting molecules to products. The reactions progressed successfully with a wide range of substrate scope and attained the products in good to excellent yields in a short reaction time in ethanol/water (1:1) medium. Greatly, catalysts can be recovered and reused for few cycles with significant reactivity.

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.