19932-84-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-1,3-Benzoxazol-2(3H)-One is used as a key intermediate in the synthesis of substituted triazoles, which are known as potent ABA (Abscisic Acid) receptor pan-antagonists. These ABA receptor antagonists play a crucial role in the development of novel pharmaceuticals targeting various diseases and conditions, including those related to hormonal regulation and stress response in plants and animals.
Used in Chemical Synthesis:
Due to its unique chemical structure and reactivity, 6-Chloro-1,3-Benzoxazol-2(3H)-One is also used as a building block in the synthesis of various other organic compounds. Its versatility allows it to be employed in the development of new materials, dyes, and other specialty chemicals across different industries.

InChI:InChI=1/C7H4ClNO2/c8-4-1-2-5-6(3-4)11-7(10)9-5/h1-3H,(H,9,10)

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 66441-23-4 2-[4-(6-Chloro-benzooxazol-2-yloxy)-phenoxy]-propionic acid ethyl ester 
• 66441-23-4 fenoxaprop-p-ethyl 
• 108-43-0 3-monochlorophenol 
• 49782-76-5 3-chlorophenyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 28443-50-7 2-amino-5-chlorophenol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 19213-72-0 ethyl 1-imidazolecarboxylate 
• 95-55-6 2-amino-phenol 
• 89-73-6 salicylhydroxamic acid 
• 131761-59-6 7-chloro-2,4-dihydroxy-2H-1,4-benzoxazin-3-one 

Downstream Products

• 87200-36-0 3--6-chloro-2-oxobenzoxazole 
• 108176-86-9 6-chloro-3-<4-(N-piperidinomethyl)phenylaminomethyl>benzoxazolin-2-one 
• 554-68-7 triethylamine hydrochloride 
• 120007-57-0 6-Chloro-3-[2-(4-nitro-phenyl)-2-oxo-ethyl]-3H-benzooxazol-2-one 
• 120007-46-7 6-chloro-3-phenacylbenzoxazolinone 
• 22876-20-6 6-chlorobenzo[d]oxazole-2(3H)-thione 
• 203862-51-5 (+/-)-6-chloro-3-[4-(4-chlorobenzyl)morpholin-2-ylmethyl]-3H-benzoxazol-2-one 
• 1105710-32-4 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one 
• 1609694-10-1 6-chloro-3-((methyl(2-morpholinopropyl)amino)methyl)benzo[d]oxazol-2(3H)-one 
• 924135-16-0 C₁₈H₁₆ClFN₂O₂ 
• 1609694-16-7 6-chloro-3-((cyclopropyl(3-methoxybenzyl)amino)methyl)benzo[d]oxazol-2(3H)-one 
• 1609694-21-4 6-chloro-3-((2-phenylpiperidin-1-yl)methyl)benzo[d]oxazol-2(3H)-one 
• 22876-20-6 6-chloro-2-mercaptobenzoxazole 
• 3621-82-7 2,6-dichloro-1,3-benzoxazole 

Relevant academic research and scientific papers

Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone

Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahydroisoindoline-1,3-dione scaffold to provide 25 compounds (1a-1u and 2a-2d). The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X-ray single-crystal diffraction. Some of these compounds (1g, 1h, 1j, 1k) exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli at a rate of 375 g AI·ha-1. Among them, compounds 1h and 1j displayed the best post-emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha-1, respectively, which are superior to that of the commercial acifluorfen (44.3 g AI·ha-1). Field trials demonstrated that compound 1h exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound 1h could potentially be used as a post-emergence herbicide for maize fields. Two series of tetrahydroisoindoline-1,3-diones containing an alkoxycarbonyl substituted 2-benzoxazolinone moiety were designed and synthesized. Compound 1h displayed excellent herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 g AI·ha-1, and compound 1h could potentially be used as a new post-emergence herbicide for maize fields.

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.

Synthesis method of 2,6-dichlorobenzooxazole

The invention relates to the field of organic synthesis, and particularly relates to a synthesis method of 2,6-dichlorobenzooxazole. The synthesis method comprises the following steps: adding benzoxazolone and phosphorus oxychloride in a reaction container, carrying out dissolving by stirring, then adding a chlorination reagent, carrying out a chlorination reaction to obtain the 6-dichlorobenzooxazole, adding a certain amount of a catalyst, carrying out heating for reflux, carrying out a reaction for 6-12 hours, removing the solvent after the reaction is ended, and carrying out reduced pressure distillation to obtain the product 2,6-dichlorobenzooxazole. According to the preparation method of the 2,6-dichlorobenzooxazole, the route is short, the yield is high, operation is simple and convenient, three wastes (waste gas, waste water and industrial residue) generated in a reaction process are few, and the method is suitable for large-scale industrial production. In addition, the phosphorus oxychloride is used for replacing virulent phosgene, diphosgene, solid phosgene or phosphorus pentachloride, the safety coefficient during production is improved, and environment friendliness is achieved.

Method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as chlorinating agent

The invention provides a method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as a chlorinating agent. The method comprises the followingsteps: step 1, respectively preparing 2-benzoxazolone and 2-mercapto benzoxazole by taking the o-aminophenol as a raw material; step 2, preparing the 2-chlorobenzoxazole by taking the 2-mercapto benzoxazole as a raw material and the solid triphosgene as the chlorinating agent; step 3, preparing 6-chlorobenzoxazolone by taking TCCA and the 2-benzoxazolone as raw materials; step 4, preparing 2-mercapto-6-chlorobenzoxazole; step 5, preparing the 2,6-dichlorobenzoxazole by taking the 2-mercapto-6-chlorobenzoxazole as a raw material and the solid triphosgene as the chlorinating agent. The method provided by the invention is a brand-new preparation method, which has the advantages of less corrosion to equipment, high yield, less reaction time, mild reaction conditions, less by-products and reduced environmental pollution.

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.

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.

General and efficient synthesis of benzoxazol-2(3H)-ones: Evolution of their anti-cancer and anti-mycobacterial activities

A novel class of benzo[d]oxazol-2(3H)-one derivatives has been synthesized and their in vitro cytotoxicity against human pancreatic adenocarcinoma and human non-small cell lung carcinoma cancer cell lines was evaluated. Many of these compounds were found to display excellent to moderate activity. Among them, 6b, 6l, 6n and 6x were identified as lead molecules. In particular, 6l and 6n were found to be potent against the pancreatic adenocarcinoma cell line whereas the 6x was found to be effective against the human non-small cell lung carcinoma cell line. Conversely, the compounds 6l-x were found to be ineffective against Mycobacterium tuberculosis. Of the various molecules, 6h showed promising anti-mycobacterial activity, with an IC50 value equal to that of ciprofloxacin.

Development of benzo[d]oxazol-2(3H)-ones derivatives as novel inhibitors of Mycobacterium tuberculosis InhA

A series of twenty seven substituted 2-(2-oxobenzo[d]oxazol-3(2H)-yl)acetamide derivatives were designed based on our earlier reported Mycobacterium tuberculosis (MTB) enoyl-acyl carrier protein reductase (InhA) lead. Compounds were evaluated for MTB InhA inhibition study, in vitro activity against drug-sensitive and -resistant MTB strains, and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, 2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)-N-(5-nitrothiazol-2-yl)acetamide (30) was found to be the most promising compound with IC50 of 5.12 ± 0.44 μM against MTB InhA, inhibited drug sensitive MTB with MIC 17.11 μM and was non-cytotoxic at 100 μM. The interaction with protein and enhancement of protein stability in complex with compound 30 was further confirmed biophysically by differential scanning fluorimetry.