36216-80-5

Basic information

• Product Name: 3-Amino-1,2-benzisoxazole
• Synonyms: OTAVA-BB BB7119710108;AKOS BBS-00002920;1,2-BENZISOXAZOL-3-AMINE;IFLAB-BB F1935-0009;BENZO[D]ISOXAZOL-3-YLAMINE;3-Amino-1,2-benzisoxazole;3-Amino-1,2-benzisoxazole 97%;1,2-Benzisoxazol-3-amine ,97%
• CAS NO: 36216-80-5
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.14
• Product Categories: Amines;Fused Ring Systems
• Mol File: 36216-80-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 311.6°C at 760 mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.317g/cm³
• Vapor Pressure: 0.000559mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.04±0.30(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3-Amino-1,2-benzisoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-1,2-benzisoxazole(36216-80-5)
• EPA Substance Registry System: 3-Amino-1,2-benzisoxazole(36216-80-5)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-36-25
• Safety Statements: 26-36/37/39-37/39-45
• HazardClass: IRRITANT
• Hazardous Substances Data: 36216-80-5(Hazardous Substances Data)

Usage

Chemical Properties

White to light brown solid

Uses

1,2-Benzisoxazol-3-amine is a useful reagent for the preparation of benzisoxazole sulfonamides useful in treatment of diseases

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 1293, 1989 DOI: 10.1002/jhet.5570260515

InChI:InChI=1/C7H6N2O/c8-7-5-3-1-2-4-6(5)10-9-7/h1-4H,(H2,8,9)

Upstream product

• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 52561-89-4 N-benzo[d]isoxazol-3-yl-benzamide 
• 73498-26-7 4-benzo[d]isoxazol-3-ylazo-N,N-dimethyl-aniline 
• 82361-00-0 2,6-dichloro-N-(3-benzisoxazolyl)benzamide 
• 81465-86-3 1-(2,6-dichlorobenzoyl)-3-(3-benzisoxazolyl)urea 
• 1093209-19-8 4-[3-(4-chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid benzo[d]isoxazol-3-ylamide trifluoroacetate 
• 627869-94-7 3-amino-benzo[d]isoxazole-5-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide 

Relevant articles and documents

Application of a recyclable fluorous oxime in the convenient synthesis of 3-amino-1,2-benzisoxazoles and 4-amino-1H-2,3-benzoxazines

A microwave-assisted, fluorous synthetic route to 3-amino-1,2- benzisoxazoles and 4-amino-1H-2,3-benzoxazines has been developed. The strategy comprises linking the respective 2-fluorobenzonitrile or 2-(bromomethyl) benzonitrile to a fluorous oxime tag to give an aryloxime intermediate which then undergoes cyclization with concomitant cleavage of the substrate-tag in acidic conditions to provide the desired product in good to moderate yields. In addition, the aryloxime intermediate could be subjected to further reactions to expand the compound library. The product could be easily separated using fluorous solid-phase extraction (F-SPE) and the fluorous ketone recovered could be converted back to the fluorous oxime and reused in the next run of the synthesis.