23997-94-6

Basic information

• Product Name: 5-BENZOXAZOLOL, 2-METHYL-
• Synonyms: 5-BENZOXAZOLOL, 2-METHYL-;2-methylbenzo[d]oxazol-5-ol;5-hydroxy-2-methylbenzo[d]oxazole;2-methyl-1,3-benzoxazol-5-ol
• CAS NO: 23997-94-6
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• Mol File: 23997-94-6.mol

Chemical Properties

• Melting Point: 164-165 °C
• Boiling Point: 278.7±13.0 °C(Predicted)
• Appearance: /
• Density: 1.305±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.70±0.10(Predicted)
• CAS DataBase Reference: 5-BENZOXAZOLOL, 2-METHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZOXAZOLOL, 2-METHYL-(23997-94-6)
• EPA Substance Registry System: 5-BENZOXAZOLOL, 2-METHYL-(23997-94-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 23997-94-6(Hazardous Substances Data)

Usage

Application

2-Methylbenzo[d]oxazol-5-ol is a useful research chemical.

Upstream product

• 23997-82-2 2,5-dimethoxyphenyl methyl ketone oxime 
• 24558-42-7 (E)-1-(2,5-dihydroxyphenyl)ethanone oxime 
• 24558-42-7 1-(2,5-dihydroxyphenyl)ethan-1-one oxime 
• 79-24-3 Nitroethane 
• 123-31-9 hydroquinone 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 937263-24-6 2-methyl-5-(2-methyl-4-nitrophenoxy)benzo[d]oxazole 
• 1222555-20-5 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2-methyl-1,3-benzoxazol-6-yl)-1,3-dihydro-2H-indol-2-one 
• 90418-93-2 2-methyl-1,3-benzothiazole-5-carbonitrile 

Relevant articles and documents

Imaging Mutant Huntingtin Aggregates: Development of a Potential PET Ligand

Mutant huntingtin (mHTT) protein carrying the elongated N-Terminal polyglutamine (polyQ) tract misfolds and forms protein aggregates characteristic of Huntington's disease (HD) pathology. A high-Affinity ligand specific for mHTT aggregates could serve as a positron emission tomography (PET) imaging biomarker for HD therapeutic development and disease progression. To identify such compounds with binding affinity for polyQ aggregates, we embarked on systematic structural activity studies; lead optimization of aggregate-binding affinity, unbound fractions in brain, permeability, and low efflux culminated in the discovery of compound 1, which exhibited target engagement in autoradiography (ARG) studies in brain slices from HD mouse models and postmortem human HD samples. PET imaging studies with 11C-labeled 1 in both HD mice and WT nonhuman primates (NHPs) demonstrated that the right-hand-side labeled ligand [11C]-1R (CHDI-180R) is a suitable PET tracer for imaging of mHTT aggregates. [11C]-1R is now being advanced to human trials as a first-in-class HD PET radiotracer.

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.

One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes

PPA-activated nitroalkanes are employed in the design of a one-pot cascade transformation involving metal-free and oxidant-free direct ortho-C-H functionalization, followed by Beckman rearrangement and intramolecular cyclocondensation to produce benzoxazoles and benzobisoxazoles directly from easily available phenols.

IRE-1α INHIBITORS

PROBLEM TO BE SOLVED: To provide compounds which directly inhibit inositol requiring enzyme 1 (IRE-1α activity) in vitro, prodrugs, and pharmaceutically acceptable salts thereof. SOLUTION: The present invention provides a compound represented by formula (A) [R3 and R4 are H or the like; Q5-Q8, together with the benzene ring to which they are attached, form a benzofused ring, where at least one of Q5-Q8 is a heteroatom selected from N, O, and S. COPYRIGHT: (C)2016,JPOandINPIT

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.

Processes and intermediates for the preparation of N4-phenyl-quinazoline-4-amine derivatives

This invention provides compounds of Formula (I), wherein B, G, A, E, R1, R2, R3, m and n are as defined herein, which are useful as type I receptor tyrosine kinase inhibitors, and methods of use thereof in the treatment of hyperproliferative disorders in mammals.