22876-16-0

Usage

Uses

Used in Textile Industry:
6-METHYL-1,3-BENZOXAZOL-2(3H)-ONE is used as a fluorescent whitening agent for enhancing the whiteness and brightness of textiles. It absorbs ultraviolet light and emits blue light, improving the overall appearance of fabrics.
Used in Paper Industry:
In the paper industry, 6-METHYL-1,3-BENZOXAZOL-2(3H)-ONE serves as an optical brightening agent, increasing the brightness and whiteness of paper products. Its ability to absorb ultraviolet light and emit blue light contributes to the improved visual appeal of paper materials.
Used in Plastic Industry:
6-METHYL-1,3-BENZOXAZOL-2(3H)-ONE is utilized as a brightening agent in the plastic industry to enhance the appearance of plastic materials by increasing their whiteness and brightness through the absorption of ultraviolet light and emission of blue light.
Used in Pharmaceutical Research:
6-METHYL-1,3-BENZOXAZOL-2(3H)-ONE has been studied for its potential applications in medicine, particularly for its antioxidant properties, which may contribute to the prevention of cellular damage caused by reactive oxygen species. Additionally, its anti-cancer properties are being investigated for possible use in the development of new therapeutic agents.

InChI:InChI=1/C8H7NO2/c1-5-2-3-6-7(4-5)11-8(10)9-6/h2-4H,1H3,(H,9,10)

Upstream product

• 158671-29-5 N,2-dihydroxy-4-methylbenzamide 
• 77287-34-4 formamide 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 530-62-1 1,1'-carbonyldiimidazole 
• 57-13-6 urea 
• 29430-39-5 m-tolyl chloroformate 
• 700-38-9 2-nitro-5-methylphenol 
• 108-39-4 3-methyl-phenol 
• 33222-69-4 3-methylphenyl carbamate 
• 201230-82-2 carbon monoxide 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 131761-56-3 2,4-dihydroxy-7-methyl-2H-1,4-benzoxazin-3-one 

Downstream Products

• 1208448-80-9 3-benzyl-6-methyl-3H-benzooxazol-2-one 
• 910322-62-2 (6-methyl-2-oxobenzooxazol-3-yl)acetic acid benzyl ester 
• 1246928-35-7 C₁₆H₁₅NO₃ 

Relevant academic research and scientific papers

Gold nanoparticle-catalyzed cyclocarbonylation of 2-aminophenols

Gold nanoparticles supported on hydrotalcite acted as a highly efficient catalyst for the cyclocarbonylation of 2-aminophenols to 2-benzoxazolinones without any additives. After the cyclocarbonylation, the hydrotalcite-supported gold nanoparticles could be reused without loss of catalytic efficiency.

Design and synthesis of novel benzo[ d[oxazol-2(3H)-one derivatives bearing 7-substituted-4-enthoxyquinoline moieties as c-Met kinase inhibitors

Analysis of the results of studies of docking 1 and 7a with c-Met kinase led to the identification of benzo [d]oxazol-2(3H)-one-quinolone derivatives as potential inhibitors of this enzyme. A molecular hybrid strategy, using a 4-ethoxy-7-substituted-quinoline core and a benzo[d]oxazol-2(3H)-one scaffold, was employed to design members of this family for study as inhibitors of the kinase and proliferation of EBC-1 cells. Most of the substances were found to display good to excellent c-Met kinase inhibitory activities. The results of a structureeactivity relationship (SAR) study led to the discovery of benzo[d]oxazol-2(3H)-one-quinolone 13, which has IC50 values of 1 nM against c-Met kinase and 5 nM against proliferation of the EBC-1 cell line.

Synthesis and biological activities of some 1,3-benzoxazol-2(3H)-one derivatives as anti-quorum sensing agents

Antibiotics are commonly used to treat microbial infections. Due to misuse or large-scale use of antibiotics, many pathogens have gained resistance which makes antibiotic treatments ineffective. The discovery that many bacteria use quorum sensing (QS) to regulate their virulence factor and pathogenicity production makes the QS system an attractive target for antimicrobial therapy. A series of 1,3-benzoxazol-2(3H)-one derivatives were designed and synthesized as QS inhibitors (QSIs) and tested for their QS inhibitory activities. In vitro quorum sensing inhibitor screen (QSIS) assay indicated that the 1,3-benzoxazol-2(3H)-one (compound 1), 5-chloro-1,3-benzoxazol-2(3H)-one (compound 6), 6-methyl-1,3-benzoxazol-2(3H)-one (compound 11), and 5-methyl-1,3-benzoxazol-2(3H)-one (compound 16), inhibit QS system in quorum sensing selector (QSIS)1 strain. These 4 QSIs also significantly reduced elastase production, biofilm formation and swarming motility of Pseudomonas aeruginosa PA01 strain. These results suggest that compound 1, 6, 11 and 16 may provide a starting point for the design and development of new anti-pathogenic drugs that restrict virulence of P. aeruginosa and possibly other clinically important human pathogens. In addition, these QSI molecules could potentially be used in combination with conventional antibiotics to increase the efficiency of disease control and to extend the life span of established antimicrobials. Georg Thieme Verlag KG Stuttgart · New York.

Method for preparing carbonyl heterocyclic compound

The invention provides a method for preparing a carbonyl heterocyclic compound, wherein Lewis base and hydrosilane are used as accelerators and can efficiently enable an ortho-substituted aniline compound to react with normal-pressure CO2 to generate corresponding carbonyl heterocyclic compounds containing different functional groups under mild conditions (100 DEG C, digital). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of CO, high-pressure CO2 and noble metal catalysts is avoided, the intermediate isocyanate does not need to be purified and separated, the pure product can be obtained only through simple suction filtration and separation after the reaction is finished, and the synthetic method is efficient and universal, is suitable for preparing a series of benzimidazolone, benzoxazolone and benzothiazolone compounds and has high industrial application value.

Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions

Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

Iron-Catalyzed Arene C-H Amidation Using Functionalized Hydroxyl Amines at Room Temperature

Herein, we report Fe(III)(TPP)Cl as an effective catalyst for promoting arene C-H amidation through intramolecular cyclization of N-tosyloxyarylcarbamate substrates. The reaction proceeds via nitrene (outer sphere pathway) C(sp2)-H i

Visible-Light-Induced Intramolecular C(sp2)-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

Catalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates have been achieved under visible-light irradiation, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic aziridines. Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate. The chemoselectivity of the reaction, with alkyl olefin aziridination ? electron deficient olefin aziridination ≈ C(sp2)-H amination ? C(sp3)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.

Rhodium(II)-Catalyzed Undirected and Selective C(sp2)-H Amination en Route to Benzoxazolones

Rhodium(II) can effectively promote the activation and cyclization of arylcarbamate substrates to yield benzoxazolones via an intramolecular nitrene C-H insertion reaction. Investigation of the substrate scope shows that the reaction undergoes selective a

Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies

Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.