271-95-4

Basic information

• Product Name: 1,2-BENZISOXAZOLE
• Synonyms: 1,2-benzoisoxazole;1-Oxa-2-aza-1H-indene;1-Oxa-2-azaindene;4,5-Benzisoazole;4,5-Benzisoxazole;1,2-BENZISOXAZOLE;ISOINDOXAZINE;INDOXAZENE
• CAS NO: 271-95-4
• Molecular Formula: C₇H₅NO
• Molecular Weight: 119.12
• EINECS: 205-983-1
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Isoxazoles
• Mol File: 271-95-4.mol
• Article Data: 39

Chemical Properties

• Melting Point: 139 °C
• Boiling Point: 90-92 °C15 mm Hg(lit.)
• Flash Point: 86°C
• Appearance: /
• Density: 1.174 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.309mmHg at 25°C
• Refractive Index: n20/D 1.561(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -2.03±0.30(Predicted)
• Water Solubility: Soluble in water. 4.1 mg/mL in water at 25°C
• Sensitive: Light Sensitive
• BRN: 2154
• CAS DataBase Reference: 1,2-BENZISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZISOXAZOLE(271-95-4)
• EPA Substance Registry System: 1,2-BENZISOXAZOLE(271-95-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 271-95-4(Hazardous Substances Data)

Usage

Uses

1,2-Benzisoxazole derivative zonisamide is a novel antiepileptic drug and is effective for the treatment of partial seizures. 1,2-Benzisoxazole is a potential substrates of rabbit liver aldehyde oxidase. It is used to produce 5-nitro-benzo[d]isoxazole. It is involved in manufacturing medicines ( antiepileptics and antipsychotics).

Definition

ChEBI: A benzoxazole in which the benzene ring is fused to a 1,2-oxazole ring across positions 4 and 5.

General Description

1,2-Benzisoxazole derivative zonisamide is a novel antiepileptic drug and is effective for the treatment of partial seizures. 1,2-Benzisoxazole is a potential substrates of rabbit liver aldehyde oxidase.

InChI:InChI=1/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H

Upstream product

• 90-02-8 salicylaldehyde 
• 94-67-7 salicylaldehyde-oxime 
• 15258-47-6 2-methoxy-N-allylaniline 
• 145508-94-7 tert-butyl 4-(iodomethyl)piperidine-1-carboxylate 
• 21013-96-7 (E)-2-hydroxylbenzaldehyde oxime 
• 1483-72-3 diphenyliodonium chloride 
• 13519-78-3 2-ethoxy-N-allylaniline 
• 76347-03-0 3-methyl-4-(O-phenyloximino)isoxazol-5(4H)-one 
• 144447-19-8 2-hydroxybenzaldehyde oxime hydrogen sulfate potassium salt 
• 80289-35-6 lauroylsalicylaldoxime 
• 80277-94-7 hexanoylsalicylaldoxime 
• 90368-32-4 2,2-dimethyl-1,3-dioxane-4,5,6-trione O-phenyloxime 
• 59417-52-6 2-(acetoxyiminomethyl)phenol 

Relevant articles and documents

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[3 + 2]-Cycloaddition of Azaoxyallyl Cations with 1,2-Benzisoxazoles: A Rapid Entry to Oxazolines

A novel and efficient [3 + 2] cycloaddition reaction of azaoxyallyl cations and 1,2-benzisoxazoles to give oxazoline derivatives has been developed. The transformation provides a rapid entry to functionalized oxazoline scaffolds under mild and transition-metal-free conditions, which will greatly expand the reaction types of heterocycle chemistry and pave the way for syntheses of bioactive compounds.

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.