1037-39-4

Usage

Chemical class

benzoxazole

Molecular structure

composed of a benzene ring with a nitro group (-NO2) attached to the fourth carbon atom and a nitro group attached to the fifth carbon atom of the benzoxazole ring

Potential applications

organic synthesis, pharmaceutical research, development of fluorescent dyes, and optical brighteners

Safety concerns

potential toxicity and hazardous nature, requires careful handling

Upstream product

• 1308881-25-5 4-nitro-2-(4-nitrobenzamido) phenyl-4-nitrobenzoate 
• 99-57-0 2-hydroxy-5-nitroaniline 
• 62-23-7 4-nitro-benzoic acid 
• 61702-43-0 2-amino-4-nitrophenol sodium salt 
• 10403-47-1 2-bromo 5-nitroaniline 
• 122-04-3 4-nitro-benzoyl chloride 
• 369-36-8 6-fluoro-3-nitroaniline 
• 1129-37-9 4-nitrobenzaldoxime 
• 105753-08-0 N-(2-Hydroxy-5-nitro-phenyl)-4-nitro-benzamide 
• 3331-11-1 4-nitro-2-(4-nitro-benzylidenamino)-phenol 

Downstream Products

• 13676-47-6 5-amino-2-(4'-aminophenyl)-benzoxazole 
• 294656-34-1 4-nitro-N-(4-(5-(4-nitrobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 423128-03-4 4-fluoro-N-(4-(5-(4-fluorobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 423128-10-3 4-chloro-N-(4-(5-(4-chlorobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-09-5 4-bromo-N-(4-(5-(4-bromobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-10-8 4-iodo-N-(4-(5-(4-iodobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 423128-05-6 4-methoxy-N-(4-(5-(4-methoxybenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-12-0 3,4-dichloro-N-(4-(5-(3,4-dichlorobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-13-1 3,4-dimethoxy-N-(4-(5-(3,4-dimethoxybenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-14-2 4-chloro-2-nitro-N-(4-(5-(4-chloro-2-nitrobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-15-3 N-(4-(5-(benzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 313554-23-3 4-amino-N-(4-(5-(4-aminobenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 423128-12-5 4-methyl-N-(4-(5-(4-methylbenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 
• 1308881-17-5 4-tert-butyl-N-(4-(5-(4-tert-butylbenzamido)benzo[d]oxazol-2-yl)phenyl)benzamide 

Relevant academic research and scientific papers

Preparation method of 2-aminobenzoxazole compound

The present invention relates to a method for preparing a 2-aminobenzoxazole compound. Comprising the following steps: (1) condensation reaction: taking o-aminophenol and nitrobenzoyl chloride compounds as raw materials, synthesizing amide intermediates in an alkaline solution system. The highly selective double-base combination system does not react with the raw material and can neutralize the acid gas generated by the reaction; (2) Cyclization reaction: acid is added to the condensation reaction solution as a catalyst, and 2-nitrobenzoxazole compounds are generated after dehydration. The solid super acid catalyst used is efficient and easy to separate and recycle; (3) hydrogenation hydrogenation reaction: 2-nitrobenzoxazole compounds are catalyzed to obtain 2-aminobenzoxazole compounds. The bi-alkali system and solid super acids used in the present invention are highly selective, product quality and yield are high. The operation is safe and simple, the raw material cost is low, in line with the green and environmentally friendly production concept, which is conducive to industrial production.

Preparation method 2 -benzooxazole compound (by machine translation)

The invention belongs to the technical field of organic compound synthesis, and particularly relates to a preparation method of 2 -benzene benzotriazole compound. The 2 - aminophenol compound is added into 1 organic solvent, then first aminophenol compounds are added, and the condensation intermediate obtained in the formula (2 -) is added to an organic solvent, and under the action of the catalyst, the reflux reaction is heated, cooled and filtered or concentrated to obtain 2 2 -benzooxazole 1 compound 2nd. 2 -benzene benzotriazole compounds are high in quality, good in stability, high in raw material utilization rate and easy to operate, and is a method suitable for large-scale industrial production. (by machine translation)

Preparation method of 2-(aminophenyl)-5-aminobenzoxazole

The invention discloses a preparation method of 2-(aminophenyl)-5-aminobenzoxazole. The preparation method concretely comprises the following steps: (1) condensing sodium 2-amino-4-nitrophenolate andnitrobenzoyl chloride to obtain an ester intermediate; (2) cyclizing the ester intermediate under the catalysis of a strong acid to obtain 2-(nitrophenyl)-5-nitrobenzoxazole; and (3) hydrogenating the2-(nitrophenyl)-5-nitrobenzoxazole under the catalysis of Pd/C to obtain the 2-(aminophenyl)-5-aminobenzoxazole. The sodium 2-amino-4-nitrophenolate and nitrobenzoyl chloride are condensed to only generate a hydroxyl-substituted acylation intermediate (that is the ester intermediate), and the amino part does not react with the nitrobenzoyl chloride, so no amide impurities are generated, the reaction selectivity is high, the yield of condensation and cyclization is up to about 90%, and the purity of the above nitro compound is about 99%.

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.

Preparation method of 2-phenylbenzoxazole compound

The invention relates to a preparation method of a 2-phenylbenzoxazole compound, comprising the following steps: (1) condensation reaction: a 2-amino phenol compound and a benzoyl chloride compound, which are used as raw materials, react in an organic solvent to obtain a condensation reaction solution; and (2) cyclization reaction: as a cyclization catalyst, acid is added into the condensation reaction solution to carry out a cyclization reaction at a certain temperature so as to obtain a cyclization reaction solution; after the reaction, an organic solvent is added for heating refluxing; andcooling filtration or liquid-separation condensation is finally carried out to obtain a 2-phenylbenzoxazole compound. The technology is simple; product post-treatment is simple; environmental pollution is less; the prepared 2-phenylbenzoxazole compound has high product quality and good stability; in addition to general use purpose, the prepared product also can be used for preparation of a high-end luminescent material; and the preparation method is a method suitable for industrial preparation.

METHOD FOR MANUFACTURING BENZOXAZOLE COMPOUNDS

A method for manufacturing benzoxazole compounds is provided and has steps of: processing a reaction between o-aminophenol or a derivative thereof and an acyl chloride compound, so as to obtain a first product; and adding the first product into a solution of polyphosphoric acid to carry out a cyclization, so as to form a benzoxazole compound.

A novel and efficient route for the synthesis of 5-nitrobenzo[d]oxazole derivatives

In this paper, we report a novel and efficient route for the synthesis of 5-nitrobenzoxazole derivatives starting from 2-fluoro-5-nitroaniline and various benzoyl chloride derivatives under solvent-free conditions at 130 °C in the presence potassium carbonate. Benzoyl chlorides easily underwent nucleophilic acyl substitution followed by intramolecular cyclization via concomitant removal of fluorine to obtain the title compounds in high yields.

Synthesis and Preliminary Biologic Evaluation of 5-Substituted-2-(4-substituted phenyl)-1,3-Benzoxazoles as A Novel Class of Influenza Virus A Inhibitors

The diversity-oriented chemistry synthesis together with the random screening approach has permitted the discovery and optimization of novel antiviral lead compounds. In this paper, a series of novel 5-substituted-2-(4-substituted phenyl)-1,3-benzoxazoles was synthesized and evaluated for their in vitro anti-influenza A virus and anti-influenza B virus activity. The activity was monitored by the MTS assay in the Madin-Darby canine kidney cells. Compound 7h showed excellent inhibitory activity and selective index against A/H3N2 (EC50=37.03μm, SI>5), which were all higher than that of the reference drug oseltamivir (EC50>59.00μm, SI>1). However, no compound displays inhibitory activity against influenza B virus.

Parallel synthesis of benzoxazoles via microwave-assisted dielectric heating

A facile route to benzoxazoles has been developed using microwave-assisted dielectric heating. The ease of synthesis and workup allowed the parallel synthesis of a 48-membered library of benzoxazoles quickly and efficiently.

Process for making 2-aryl benz (ox, thi, imid) azoles and 2-aminoaryl aminobenz (ox, thi, imid) azoles

2-(aryl)-benz(ox, thi, imid)azoles are prepared by reacting an aromatic aldehyde with hydroxylamine to form an aromatic aldehyde oxime, halogenating the oxime to form an aromatic hydroxamoyl halide, and then reacting this halide with certain aromatic amine compounds. The products may be nitrated and then reduced to form the corresponding diamines, which are useful in making PIBX polymers.