615-18-9

Usage

Uses

Used in Organic Synthesis:
2-Chlorobenzoxazole is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and the presence of the chlorine atom make it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chlorobenzoxazole is used as a key intermediate in the synthesis of specific drug molecules. Its unique structure and reactivity allow for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of 2-(2-Naphthylamino)Benzoxazole:
2-Chlorobenzoxazole is specifically used in the synthesis of 2-(2-naphthylamino)benzoxazole through a reaction with 2-amino-1-naphthalenesulfonic acid. This reaction showcases the utility of 2-chlorobenzoxazole in forming complex heterocyclic structures that may have applications in various fields, including medicinal chemistry and materials science.

Purification Methods

Purify it by fractional distillation, preferably in a vacuum. [Siedel J Prakt Chem 42 456 1890, Katz J Am Chem Soc 75 712 1953, Meyer & Sigel J Org Chem 42 2769 1977, Beilstein 27 H 43, 27 II 17.]

InChI:InChI=1/C7H4ClNO/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H

Upstream product

• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 2382-96-9 2-sulfanyl-1,3-benzoxazole 
• 273-53-0 benzoxazole 
• 10026-13-8 phosphorus pentachloride 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 7732-18-5 water 
• 40888-01-5 3-ethylbenzo[d]oxazole-2(3H)-thione 
• 13673-63-7 3-methylbenzoxazole-2-thione 
• 95-55-6 2-amino-phenol 
• 3621-82-7 2,6-dichloro-1,3-benzoxazole 
• 4570-41-6 1,3-benzoxazol-2-amine 

Downstream Products

• 16485-05-5 ceftriaxone 
• 7009-53-2 N-benzoxazol-2-yl-N-benzyl-N',N'-dimethyl-propanediyldiamine 
• 123773-64-8 phenyl 2-benzoxazolyl thioether 
• 86971-24-6 2-(benzylthio)benzo[d]oxazole 
• 92148-95-3 N-(4-methoxyphenyl)-1,3-benzoxazol-2-amine 
• 26946-72-5 N-(4-nitrophenyl)-1,3-benzoxazol-2-amine 
• 6631-42-1 N-phenyl-1,3-benzoxazol-2-amine 
• 39208-33-8 N-(3-nitrophenyl)benzo[d]oxazol-2-amine 
• 50400-41-4 2-phenoxy-1,3-benzoxazole 
• 59-49-4 2-Benzoxazolinone 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 15062-88-1 2-hydrazino-1,3-benzoxazole 
• 39223-94-4 2-chloro-6-nitro-benzoxazole 
• 57260-44-3 1-benzooxazol-2-yl-4-[3-(4-methoxy-phenyl)-acryloyl]-piperazine 

Relevant academic research and scientific papers

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.

Novel benzoxazole derivatives featuring rhodanine and analogs as antihypergycemic agents: synthesis, molecular docking, and biological studies

A novel series of benzoxazolyl linked benzylidene based rhodanine and their cyclic analogs were synthesized, characterized and evaluated for their α-amyloglucosidase inhibitory activity. Out of eight target compounds, two compounds (4b and 5b) displayed potent inhibitory activity against α-amyloglucosidase with IC50 values in the range of 0.24 ± 0.01–0.94 ± 0.01 μM as compared to standard drug acarbose. Among all the tested compounds, compound 5b containing rhodanine at 3-position of phenyl was found to be the most active inhibitor of α-amyloglucosidase. Docking studies showed the existence of potential H-bonding interactions between synthesized compounds and α-glucosidase which might be responsible for good biological activity.

Method for preparing halogenated (hetero) aromatic hydrocarbons

The invention relates to a method for preparing halogenated (hetero) aromatic hydrocarbons. The halogenated (hetero) aromatic hydrocarbons are prepared from cheap and easily available perfluorobutyl iodide, carbon tetrabromide and carbon tetrachloride as iodinated, brominated and chlorinated reagents respectively under the action of alkali catalysis (promotion). The method comprises the following steps: firstly, (hetero) aromatic hydrocarbons, a halogenated reagent and an inorganic base are placed in an organic solvent, stirred at room temperature and monitored with TLC until a substrate disappears, and the reaction is stopped; then, a reaction mixed solution is poured into water and extracted, an organic phase is dried, and the organic solvent is removed under reduced pressure; finally, silica-gel column chromatography is performed on a crude product, and a product is obtained. Purification can also be performed by recrystallization. The method has the advantages that the synthetic route is wide in substrate range, raw materials and reagents are cheap and easily available, operation is simple, conditions are mild, yield is high, energy consumption is reduced, the reaction route is safe, gram-grade preparation can be performed and the like.

OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF

The invention relates to octahydropyrrolo [3, 4-c] pyrrole derivatives and uses thereof. Compounds and pharmaceutical compositions comprising the compounds provided herein are used for antagonizing orexin receptors. The invention also relates to processes for preparing the compounds and pharmaceutical compositions, and uses thereof in treating or preventing a disease related to orexin receptors.

Efficient transposition of the sandmeyer reaction from batch to continuous process

The transposition of Sandmeyer chlorination from a batch to a safe continuous-flow process was investigated. Our initial approach was to develop a cascade method using flow chemistry which involved the generation of a diazonium salt and its quenching with copper chloride. To achieve this safe continuous process diazotation, a chemometric approach (Simplex method) was used and extrapolated to establish a fully continuous-flow method. The reaction scope was also examined via the synthesis of several (het)aryl chlorides. Validation and scale-up of the process were also performed. A higher productivity was obtained with increased safety.

Synthesis, biological evaluation and molecular docking study of N-arylbenzo[d]oxazol-2-amines as potential α-glucosidase inhibitors

A novel series of N-arylbenzo[d]oxazol-2-amines (4a–4m) were synthesized and evaluated for their α-glucosidase inhibitory activity. Compounds 4f–4i, 4k and 4m displayed potent inhibitory activity against α-glucosidase with IC50values in the range of 32.49?±?0.17–120.24?±?0.51?μM as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of α-glucosidase with an IC50value of 32.49?±?0.17?μM. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of α-glucosidase with a Kivalue of 31.33?μM. Binding interaction of compound 4g with α-glucosidase was explored by molecular docking simulation.

A convenient one-pot synthesis of N-substituted 2-aminoazole derivatives

A practical protocol for the one-pot synthesis of N-substituted 2-aminoazole derivatives is described, employing simple azole substrates, nitrogen nucleophiles, lithium tert-butoxide as the base, and iodine to mediate carbon-nitrogen bond formation. This method proceeds at room temperature under an air atmosphere using a normal benchtop set-up, or can be performed conveniently using microwave irradiation. Georg Thieme Verlag Stuttgart - New York.

Synthesis and insecticidal activity of novel dihalopropene derivatives containing benzoxazole moiety: A structure-activity relationship study

Ten dichloropropene derivatives containing benzoxazole moiety were synthesized and bioassayed in order to determine their in vivo insecticidal activity. The structures of obtained compounds were identified by 1H NMR, MS and elemental analyses. The bioassay results indicated that compound 2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-5-(trifluoromethyl) benzo[d]oxazole (5i, R1 is trifluoromethyl, R2 is H and n is 3) had the optimal structure with best insecticidal activity against Spodoptera exigua (100%) at 1 mg/L concentration, highlighting the importance of trifluoromethyl group. The structure-activity relationship of the synthesized compounds was discussed as well.

Synthesis of new chiral ferrocenyl P,N-ligands with a benzoxazole ring and their application in Ag-catalyzed asymmetric [3+2] cycloaddition

New chiral ferrocenyl P,N-ligands with a benzoxazole ring as the N-donor group have been synthesized from 2-aminophenol through a three-step transformation and successfully employed in the Ag-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes. High diastereoselectivities, excellent enantioselectivities, and good yields have been achieved for a variety of substrates, demonstrating the potential of these new P,N-ligands in asymmetric catalysis.

Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.