19219-99-9

Usage

Chemical Properties

BEIGE CRYSTALLINE CHUNKS

InChI:InChI=1/C8H6ClNO/c1-5-10-7-4-6(9)2-3-8(7)11-5/h2-4H,1H3

Upstream product

• 60-35-5 acetamide 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 53088-03-2 4-chloro-2-ethylideneamino-phenol 
• 87974-51-4 5'-chloro-2'-hydroxyacetophenoneoxime 
• 55682-66-1 deca-1,3-diyne 
• 78-39-7 Triethyl orthoacetate 
• 89-64-5 p-chloro-o-nitrophenol 
• 28443-50-7 2-amino-5-chlorophenol 
• 144-55-8 sodium hydrogencarbonate 
• 1445-45-0 Trimethyl orthoacetate 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 17749-24-5 3-oxo-dithiobutyric acid methyl ester 
• 123-54-6 acetylacetone 
• 1019187-32-6 5'-chloro-2'-hydroxyacetophenone imine 

Downstream Products

• 13452-16-9 5-chloro-2-methyl-6-nitrobenzoxazole 
• 88787-40-0 4-amino-2-chloro-5-hydroxy-benzenesulfonic acid 
• 61931-68-8 2-methyl-5-phenylbenzo[d]oxazole 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 1351403-33-2 5-(sec-butoxy)-2-methylbenzoxazole 
• 136663-38-2 (2-methyl-1,3-benzoxazol-5-yl)methanol 
• 5676-57-3 5-Methoxy-2-methyl-benzoxazole 
• 903556-80-9 2-methylbenzo[d]oxazole-5-carbonitrile 
• 1459695-33-0 C₂₅H₂₂ClF₂N₃O₄ 
• 1459695-32-9 C₂₅H₂₂ClF₂N₃O₃ 
• 1459695-31-8 C₂₀H₂₀ClF₂N₃O₃ 
• 72745-76-7 5-amino-2-methylbenzoxazole 
• 1445972-36-0 C₁₆H₁₃N₃O₂ 

Relevant academic research and scientific papers

Use of zeolite catalysts for efficient synthesis of benzoxazoles via Beckmann rearrangement

Substituted benzoxazoles have been synthesized in very good yields starting from o-acylphenol oximes via Beckmann rearrangement using zeolite catalysis.

Metal free montmorillonite KSF clay catalyzed practical synthesis of benzoxazoles and benzothiazoles under aerobic conditions

An efficient method for the synthesis of benzoxazoles and benzothiazoles via montmorillonite KSF clay catalyzed condensation reaction between 2-aminophenols or 2-aminothiophenols and β-diketones is reported. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on aryls. The reaction is metal free and proceeds without the exclusion of air or moisture, and further the catalyst can be recycled up to 3–5 catalytic cycles.

Multicatalytic Beckmann rearrangement of 2-hydroxylarylketone oxime: Switchable synthesis of benzo[d]oxazoles and N-(2-hydroxylaryl)amides

A switchable synthesis route is developed for benzo[d]oxazole derivatives and (2-hydroxylaryl)benzamide from 2-hydroxylbenzeneketoxime using organomolecules (BOP-Cl, and CNC) and Lewis acid cocatalyzed Beckmann rearrangement (BR) reaction. Further, this reaction is switched using different organocatalysts.

Sodium dichloroiodate promoted C-C bond cleavage: An efficient synthesis of 1,3-Benzazoles via condensation of o -amino/mercaptan/hydroxyanilines with β -diketones

An efficient aqueous sodium dichloroiodate (NaICl 2) mediated protocol is developed for the synthesis of benzofused azoles by the cyclization of 2-amino anilines/thiophenols/phenols with β-diketone compounds. The reactions gave moderate to good yield of the corresponding 2-substituted benzimidazoles/benzothiazoles/benzoxazoles under mild conditions. This tandem process involved a C-C bond cleavage and C-N bond formation. Graphical Abstract?: SYNOPSIS A facile and single protocol for the synthesis of three versatile 1,3-benzazoles viz 2-substituted 1H-benzimidazoles, benzoxazoles and benzothiazoles from readily available starting materials, 1,3-diketones and corresponding o-amino anilines/thiophenols/phenols, by aqueous sodium dichloroiodate (NaICl 2) mediated C—C bond cleavage has been developed. The reaction provides a rapid access to these 1, 3-benzazoles in good yields, thus speeding up the drug discovery process.[Figure not available: see fulltext.].

p-Toluenesulfonic acid-catalyzed metal-free formal [4?+?1] heteroannulation via N[sbnd]H/O[sbnd]H/S[sbnd]H functionalization: One-pot access to 2-aryl/hetaryl/alkyl benzazole derivatives

A concise and direct one-pot [4?+?1] synthetic strategy for the construction of 2-substituted benzazoles such as benzoxazoles and benzothiazoles has been disclosed in high yields (80–98%) by cascade coupling reaction of 2-amino(thio)phenols with β-oxodithioesters. The current approach enables N[sbnd]H/O[sbnd]H/S[sbnd]H functionalization in one-pot under solventless condition leading to diverse benzazoles without use of any external metal. A wide range of 2-amino(thio)phenols and β-oxodithioesters are compatible toward this transformation with excellent functional group tolerance. Furthermore, we preempt the wider implications of this novel strategy by demonstrating its compatibility toward versatile diversification of DNA Topoisomerase-II inhibitors.

A benzoxazole derivative synthesis method

A synthetic method of benzoxazole derivative belongs to the technical field of organic chemistry synthesis. Raw material of a variety of o-hydroxyphenyl ketimines, an oxidant of iodobenzene diacetate and an additive of alkali are subjected to a simple process comprising one-step oxidation rearrangement, concentration and purification in a solvent at room temperature to obtain a product. This method has the characteristics of certain universality, mild reaction conditions, low production equipment requirement, simple technology, easily obtained raw materials, short reaction time and higher efficiency. Benzoxazole derivative products with high yield and good quality can be prepared by adopting the method of the invention; the method can be widely used in industrial production of benzoxazole derivatives; the products prepared by the method of the invention can be widely used as fluorescent whitening agents, dyeing agents, preservatives, rubber vulcanization accelerators and organic electroluminescent materials, as well as antistatic agent for the plastic films; therefore, the invention has good market application prospects.

Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement

A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Synthesis of benzoxazoles from 2-aminophenols and β-diketones using a combined catalyst of br?nsted acid and copper iodide

Cyclization reactions of 2-aminophenols with β-diketones catalyzed by a combination of Br?nsted acid and CuI are presented. Various 2-substituted benzoxazoles were obtained through these reactions. Different substituents such as methyl, chloro, bromo, nitro, and methoxy on 2-aminophenol are tolerated under the optimized reaction conditions.

Application of nano SnO2 as a green and recyclable catalyst for the synthesis of 2-aryl or alkylbenzoxazole derivatives under ambient temperature

Application of nano SnO2 as an efficient and benign catalyst has been explored for the synthesis of 2-aryl or alkylbenzoxazole derivatives via condensation reaction of aldehyde with 2-aminophenol. The reactions proceed under heterogeneous and mild conditions in ethanol at room temperature to provide 2-aryl or alkylbenzoxazoles in high yields.