891-43-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitro-2-phenyl-1,3-benzoxazole is used as an intermediate for manufacturing various drugs and pharmaceutical products due to its potential pharmacological activities.
Used in Medicinal Chemistry Research:
5-Nitro-2-phenyl-1,3-benzoxazole is used as a valuable candidate for medicinal chemistry research and drug development due to its unique chemical structure.
Used in Organic Synthesis:
5-Nitro-2-phenyl-1,3-benzoxazole is used in organic synthesis for the preparation of various chemical compounds.
Used in Bioimaging Applications:
5-Nitro-2-phenyl-1,3-benzoxazole is used as a fluorescent probe in bioimaging applications, allowing for the visualization and study of biological processes.

Upstream product

• 3230-49-7 2-hydroxy-5-nitro-N-benzylideneaniline 
• 32471-06-0 (2,4-dinitro-phenoxy)-phenyl-acetic acid 
• 100-47-0 benzonitrile 
• 98-88-4 benzoyl chloride 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 591-50-4 iodobenzene 
• 70886-33-8 5-nitro-benzooxazole 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 737765-82-1 N-(2-bromo-5-nitrophenyl)benzamide 
• 65-85-0 benzoic acid 
• 98-09-9 benzenesulfonyl chloride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 71-43-2 benzene 
• 1254970-95-0 N-nitro-О-(4-nitrophenyl)hydroxylamine 

Downstream Products

• 169170-97-2 (5-nitro-2-phenyl-benzoxazol-4-yl)acetonitrile 
• 41373-37-9 5-amino-2-phenyl-1,3-benzoxazole 
• 1024529-54-1 2-(2,4-dichlorophenoxy)-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide 
• 33832-28-9 N-(2-phenyl-1,3-benzoxazol-5-yl)benzamide 
• 118383-49-6 2-Imino-5-(2-phenyl-benzooxazol-5-ylmethyl)-thiazolidin-4-one 
• 118383-48-5 methyl 3-(2-phenylbenzoxazol-5-yl)-2-chloropropionate 

Relevant academic research and scientific papers

Quantum mechanical and spectroscopic (FT-IR, FT-Raman, 1H NMR and UV) investigations of 5-nitro-2-phenylbenzoxazole

The optimized molecular structure, vibrational wavenumbers, corresponding vibrational assignments of 5-nitro-2-phenylbenzoxazole have been investigated experimentally and theoretically. The energy and oscillator strength calculated by Time Dependent Density Functional Theory results almost compliments with experimental findings. Gauge-including atomic orbital 1H-NMR chemical shifts calculations were carried out and compared with experimental data. The HOMO and LUMO analysis is used to determine the charge transfer with in the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. molecular electrostatic potential was performed by the DFT method and the infrared intensities and Raman activities are also been reported. Fist hyperpolarizability is calculated in order to find its role in nonlinear optics. Antimicrobial properties indicated that the title compound possessed a broad spectrum activity against the tested Gram-positive, Gram-negative bacteria.

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.

Pd/Cu-Catalyzed C-H/C-H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates

A highly efficient method for the selective formal C-H/C-H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity, one-pot procedures, and the late-stage functionalization of complex molecules without the use of oxidants, offering a promising strategy for the transition-metal-catalyzed C-H arylation of azoles.

Acid-promoted cleavage of the C–C double bond of N-(2-Hydroxylphenyl)enaminones for the synthesis of benzoxazoles

An acid-mediated selective cleavage of C–C double bond of N-(2-hydroxylphenyl)enaminones with formation a new C–O bond for the synthesis of 2-substituted benzoxazoles has been developed. This protocol proceeds under transition metal- and oxidant-free conditions with broad functional group tolerance. The oxidative cleavage of C–C double bond of N-(2-hydroxylphenyl)enaminone is also realized using NCS or NFSI as oxidants with release of 2,2-dihalogen-acetophenone fragments.

A 2 - substituted benzoxazole derivative of the preparation method

The invention discloses a 2 - substituted benzoxazole derivative of the preparation method, its reaction as follows: . The present invention can be 2 - substituted pyrrole derivatives, acetophenone derivatives can be obtained and at the same time 2, 2 - dihalo acetophenone derivatives; and through the C (sp2 ) - C (sp2 ) At the same time selectively fracture of the aromatization. The method of the invention the resulting raw materials are easy, high yield, mild reaction conditions, the reaction time is short, wide substrate range, reaction specificity is strong, easy post treatment and green environmental protection.

Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives

The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions

The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.

Phosphonium acidic ionic liquid: An efficient and recyclable homogeneous catalyst for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles

A highly efficient and green strategy for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-Aminophenol, o-phenylenediamines, and o-Aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles

N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes

A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.