23999-64-6

Basic information

• Product Name: 6-methoxy-2-methylbenzoxazole
• Synonyms: 6-methoxy-2-methylbenzoxazole;6-Methoxy-2-methyl-benzooxazole;6-Methoxy-2-Methylbenzo[d]oxazole;6-methoxy-2-methyl-1,3-benzoxazole
• CAS NO: 23999-64-6
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• EINECS: 245-978-1
• Mol File: 23999-64-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 51.5-53 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 250 °C at 760 mmHg
• Flash Point: 105 °C
• Appearance: /
• Density: 1.166 g/cm³
• Vapor Pressure: 0.0351mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: 2-8°C
• PKA: 1.06±0.30(Predicted)
• CAS DataBase Reference: 6-methoxy-2-methylbenzoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-2-methylbenzoxazole(23999-64-6)
• EPA Substance Registry System: 6-methoxy-2-methylbenzoxazole(23999-64-6)

Safety Data

• Hazardous Substances Data: 23999-64-6(Hazardous Substances Data)

Usage

General Description

6-Methoxy-2-methylbenzoxazole is a chemical compound with the molecular formula C10H9NO2 that belongs to a category of organic compounds known as benzoxazoles. These are aromatic compounds containing a benzene fused to an oxazole ring. Being an aromatic heteromonocyclic compound, it is predominantly derived from a carbon skeleton system consisting of at least one heteroatom in a ring structure. As per the chemical data, it is in powder form and has to be stored under suitable conditions due to its reactivity and sensitivity to various environmental factors. 6-methoxy-2-methylbenzoxazole finds utility in multiple chemical and pharmaceutical applications due to its unique structural properties.

InChI:InChI=1/C9H9NO2/c1-6-10-8-4-3-7(11-2)5-9(8)12-6/h3-5H,1-2H3

Upstream product

• 23997-80-0 2,4-dimethoxyacetophenone oxime 
• 51864-08-5 2-hydroxy-4-methoxyacetophenone oxime 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 1021267-09-3 2'-hydroxy-4'-methoxyacetophenone imine 
• 704-14-3 3-methoxy-6-nitro-phenol 
• 91-66-7 N,N-diethylaniline 

Downstream Products

• 114979-97-4 Dibutyl-(3-{4-[(E)-2-(6-methoxy-benzooxazol-2-yl)-vinyl]-phenoxy}-propyl)-amine 
• 780821-18-3 {4-[1-hydroxy-2-(6-methoxy-benzooxazol-2-yl)-ethyl]-phenyl}-methyl-carbamic acid tert-butyl ester 
• 58469-06-0 N-(2-hydroxy-4-methoxyphenyl)acetamide 
• 124941-85-1 2-{(E)-2-[4-(3-Chloro-propoxy)-phenyl]-vinyl}-6-methoxy-benzooxazole 

Relevant articles and documents

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.

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.

A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine

A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.