177995-40-3

Basic information

• Product Name: 4-METHOXY-1,2-BENZISOXAZOL-3-AMINE
• Synonyms: 4-METHOXY-1,2-BENZISOXAZOL-3-AMINE;4-Methoxy-1,2-benzisoxiazol-3-amine;1,2-Benzisoxazol-3-amine,4-methoxy-(9CI);3-Amino-4-methoxy-1,2-benzisoxazole;4-Methoxy-benzo[d]isoxazol-3-ylaMine;3-Amino-4-methoxybenzo[d]isoxazole;4-Methoxybenzo[d]isoxazol-3-aMine
• CAS NO: 177995-40-3
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16
• Product Categories: OXAZOLE
• Mol File: 177995-40-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 140 °C
• Boiling Point: 348.9 °C at 760 mmHg
• Flash Point: 164.8 °C
• Appearance: /
• Density: 1.304 g/cm³
• Vapor Pressure: 4.88E-05mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-METHOXY-1,2-BENZISOXAZOL-3-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-1,2-BENZISOXAZOL-3-AMINE(177995-40-3)
• EPA Substance Registry System: 4-METHOXY-1,2-BENZISOXAZOL-3-AMINE(177995-40-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• Hazardous Substances Data: 177995-40-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 2885, 1996 DOI: 10.1016/0040-4039(96)00425-X

InChI:InChI=1/C8H8N2O2/c1-11-5-3-2-4-6-7(5)8(9)10-12-6/h2-4H,1H3,(H2,9,10)

Upstream product

• 94088-46-7 2-fluoro-6-methoxybenzonitrile 
• 546-88-3 acetylhydroxamic acid 

Downstream Products

• 688781-59-1 4-(2-fluoro-4-nitrophenoxy)-1,2-benzisoxazol-3-amine 
• 688781-61-5 4-(4-amino-2-fluorophenoxy)-1,2-benzisoxazol-3-amine 
• 126940-15-6 3-amino-4-hydroxy-1,2-benzisoxazole 

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.

Novel one-pot cyclization of ortho substituted benzonitriles to 3-amino-1,2-benzisoxazoles

A novel one-pot synthesis of 3-amino-1,2-benzisoxazoles (iii), from ortho substituted benzonitriles (i), is described. The synthesis likely involves a SNAr reaction of an activated ortho halo or nitro group by a hydroxamate anion, followed by an intra-mol