66571-26-4

Basic information

• Product Name: 6-Methyl-1,2-benzisoxazol-3(2H)-one
• Synonyms: 6-Methyl-1,2-benzisoxazol-3(2H)-one;6-Methylbenzo[d]isoxazol-3(2H)-one;6-Methyl-1,2-benzoxazol-3-one;6-Methylbenzo[d]isoxazol-3(2H);6-Methyl-1,2-benzisoxazol-3-ol
• CAS NO: 66571-26-4
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.14668
• Mol File: 66571-26-4.mol

Chemical Properties

• Melting Point: 148-150 °C
• Boiling Point: 310.9 °C at 760 mmHg
• Flash Point: 141.8 °C
• Appearance: /
• Density: 1.259 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.66±0.20(Predicted)
• CAS DataBase Reference: 6-Methyl-1,2-benzisoxazol-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methyl-1,2-benzisoxazol-3(2H)-one(66571-26-4)
• EPA Substance Registry System: 6-Methyl-1,2-benzisoxazol-3(2H)-one(66571-26-4)

Safety Data

• Hazardous Substances Data: 66571-26-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
6-Methyl-1,2-benzisoxazol-3(2H)-one is utilized as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new drugs and pesticides.
Used in Medicinal Chemistry Research:
MBO has been studied for its potential as an anticonvulsant and anti-inflammatory agent. Its ability to modulate certain biological pathways and processes makes it a promising candidate for the treatment of neurological and inflammatory conditions.
Used in Antioxidant and Antibacterial Applications:
6-Methyl-1,2-benzisoxazol-3(2H)-one has demonstrated antioxidant and antibacterial properties, making it a subject of interest for research in the development of new antioxidants and antibacterial agents. These applications can be beneficial in various industries, including food preservation, cosmetics, and healthcare.
Used in Environmental Research:
MBO has been identified as a potential environmental contaminant, and its impact on aquatic organisms has been studied. Understanding the ecological effects of MBO can help in assessing its environmental risks and developing strategies for its safe handling and disposal.

Upstream product

• 158671-29-5 N,2-dihydroxy-4-methylbenzamide 
• 50-85-1 2-hydroxy-p-toluic acid 
• 4670-56-8 methyl 2-hydroxy-4-methylbenzoate 

Downstream Products

• 16302-64-0 3-Chlor-6-methyl-1,2-benzisoxazol 
• 947408-94-8 6-methyl-2-triphenylmethyl-1,2-benzisoxazol-3(2H)-one 

Relevant articles and documents

Chromatography-free, Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids to 3-hydroxybenzisoxazoles

The Mitsunobu reaction has become one of the most powerful tools to alkylate acidic pronucleophiles. A significant caveat of Mitsunobu chemistry, however, is that the reaction mixture is often plagued with purification problems owing to the phosphine oxide and hydrazine dicarboxylate by-products. In addition to the development of more readily separable Mitsunobu reagents, the product's physicochemical properties may be exploited to facilitate purification. In this regard, we present a swift and efficient preparation of 3-hydroxybenzisoxazoles by the Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids, which can be isolated by an acid–base work-up. As expected, a range of functional groups was compatible with the chemistry.

Benzimidazolones: A new class of selective peroxisome proliferator- activated receptor γ (PPARγ) modulators

A series of benzimidazolone carboxylic acids and oxazolidinediones were designed and synthesized in search of selective PPARγ modulators (SPPARγMs) as potential therapeutic agents for the treatment of type II diabetes mellitus (T2DM) with improved safety profiles relative to rosiglitazone and pioglitazone, the currently marketed PPARγ full agonist drugs. Structure-activity relationships of these potent and highly selective SPPARγMs were studied with a focus on their unique profiles as partial agonists or modulators. A variety of methods, such as X-ray crystallographic analysis, PPARγ transactivation coactivator profiling, gene expression profiling, and mutagenesis studies, were employed to reveal the differential interactions of these new analogues with PPARγ receptor in comparison to full agonists. In rodent models of T2DM, benzimidazolone analogues such as (5R)-5-(3-{[3-(5-methoxybenzisoxazol-3-yl)benzimidazol-1-yl]methyl}phenyl) -5-methylox-azolidinedione (51) demonstrated efficacy equivalent to that of rosiglitazone. Side effects, such as fluid retention and heart weight gain associated with PPARγ full agonists, were diminished with 51 in comparison to rosiglitazone based on studies in two independent animal models. (Figure presented)

PROCESS FOR PRODUCTION OF 3-[5-[4-(CYCLOPENTYLOXY)-2-HYDROXYBENZOYL]-2-[(3-HYDROXY-1,2-BEZISOXAZOL-6-YL)METHOXY]PHENYL]PROPIONATE ESTER AND INTERMEDIATE FOR THE PROCESS

A preparation method using as an intermediate 6-(halomethyl)-1,2-benzisoxazol-3(2H)-one derivative represented by general formula wherein R5 is a methyl group that is substituted with one or more optionally substituted phenyl groups, or an opti

Synthesis and biological evaluation of D-amino acid oxidase inhibitors

D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them,

BENZISOXAZOLES

The present invention concerns the compounds of formula (I), the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein m represents an integer from 1 to 3; X represents amino, hydroxy, -oxo or -Z-R1; Y is absent when X represents -Z-R1 and -(C=O)-R66 when X represents oxo; Z represents carbonyl, -oxy-carbonyl- or -NR 55-carbonyl-; R1 represents C1-4alkyl, Ar1, Ar1-C1-4a1ky1-, -NR3R4 or -Het1; R2 represents hydrogen, halo, nitro, hydroxycarbonyl-, C1-4alkyloxy or C1-4alkyl; R33 and R4 are each independently selected from hydrogen, Ar33 or C1-4alkyl; R5 represents hydrogen, C1-4alkylcarbonyl- or Ar4-carbonyl-; R6 represents a substituent selected from the group consisting of C1.4alkyl, Ar55, Ar6-C1-4alkyl- or NR7R8; R7 and R8 are each independently selected from hydrogen, Het4 or C1-4alkyl; Het1 represents a heterocycle selected from oxazolyl, isoxazolyl, imidazolyl or pyrazolyl wherein said heterocycle is optionally substituted with one, two or three substituents selected from the group consisting of amino, C1-4alkyl, hydroxy-C1-4alkyl, phenyl, phenyl-C1-4alkyl- and phenyl substituted with one or more halo substituents; Het4 represents a heterocycle selected from oxazolyl or isoxazolyl, wherein said heterocycle is optionally substituted with one or more substituents selected from the group consisting of amino, C1-4alkyl, hydroxy-C1-4alkyl-, phenyl, phenyl-Cl-4alkyl and phenyl substituted with one or more halo substituents; and Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 each independently represents phenyl optionally substituted one or where possible two or more substituents selected from halo, nitro, C1-4alkyl, hydroxy or C1-4alkyloxy-.

Benzo[d]isoxazol-3-ol DAAO inhibitors

Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia, or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutic amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein Z1 is N or CR3; Z2 is N or CR4; Z3is O or S; A is hydrogen, alkyl or M+; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc or a mixture thereof; R1, R2, R3 and R4 are independently selected from hydrogen, alkyl, hydroxy alkoxy, aryl, acyl, halo, cyano, haloalkyl, NHCOOR5 and SO2NH2; R5 is aryl, arylalkyl, heteroaryl or heteroarylalkyl; at least one of R1, R2, R3 and R4 is other than hydrogen; and at least one of Z1 and Z2 is other than N.

NOVEL BENSOPHENONE DERIVATIVES OR SALTS THEREOF

A benzophenone derivative represented by the following formula: whereinR1 represents, for example, an optionally substituted heterocyclic group, or a substituted phenyl group; Z represents, for example, an alkylene group; R2 represents, for example, a carboxyl group optionally protected with alkyl;R3 represents, for example, an optionally protected hydroxyl group; R4 represents, for example, an optionally substituted cycloalkyloxy group; and R5 represents, for example, a hydrogen atom, ???or a salt thereof has anti-arthritic activity, inhibits bone destruction caused by arthritis, and provides high safety and excellent pharmacokinetics and thus is useful as therapeutic agent for arthritis. These compounds have inhibitory effect on AP-1 activity and are useful as preventive or therapeutic agent for diseases in which excessive expression of AP-1 is involved.