203718-17-6

Basic information

• Product Name: 2,1-Benzisoxazole, 3-(4-fluorophenyl)-
• Synonyms: 2,1-Benzisoxazole, 3-(4-fluorophenyl)-
• CAS NO: 203718-17-6
• Molecular Formula: C13H8FNO
• Molecular Weight: 213.2071232
• Mol File: 203718-17-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,1-Benzisoxazole, 3-(4-fluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,1-Benzisoxazole, 3-(4-fluorophenyl)-(203718-17-6)
• EPA Substance Registry System: 2,1-Benzisoxazole, 3-(4-fluorophenyl)-(203718-17-6)

Safety Data

• Hazardous Substances Data: 203718-17-6(Hazardous Substances Data)

Usage

Chemical Class

2,1-Benzisoxazole

Substituent

4-Fluorophenyl

Position of Substituent

3-Position

Potential Applications

Medicinal chemistry (building block for pharmaceuticals and agrochemicals), therapeutic effects

Biological Activity

Studied for potential effects

Handling

Handle with care, potential hazards, use in controlled manner

Upstream product

• 271-58-9 anthranil 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 371-40-4 4-fluoroaniline 
• 3800-06-4 2-amino-4'-fluorobenzophenone 

Relevant articles and documents

Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines

Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.

Metal-Free, Visible-Light-Enabled Direct C3-H Arylation of Anthranils

An eosin Y disodium salt-catalyzed photoredox C-H arylation of anthranils is reported. A variety of aryl diazonium tetrafluoroborates were used as aryl sources, providing the C3 cross-coupled products. The in situ generated reactive radicals were trapped by anthranils, providing an alternative method to transition-metal-catalyzed C-H arylations of anthranils. Gold-catalyzed downstream transformations demonstrate the synthetic potential of these valuable building blocks.

Reactivity of 2,1-Benzisoxazole in Palladium-Catalyzed Direct Arylation with Aryl Bromides

The Pd-catalyzed direct arylation of 2,1-benzisoxazole with aryl bromides to access 3-arylbenzoisoxazoles proceeds in moderate-to-high yields with 1 mol % Pd(OAc)2 or 2 mol % PdCl(C3H5)(dppb) (dppb=1,4-bis(diphenylphosphino)butane) as the catalysts and KOAc as an inexpensive base. A wide variety of (hetero)aryl bromides have been employed successfully. Moreover, arylations followed by benzisoxazole ring opening allowed the preparation of 2-aminobenzophenones in only two steps. What a couple: The Pd-catalyzed direct arylation of 2,1-benzisoxazole with aryl bromides and 1 mol % of phosphine-free Pd(OAc)2 catalyst in association with KOAc as an inexpensive base allows the preparation of 3-arylbenzoisoxazoles in moderate-to-high yields. Moreover, the 2,1-benzisoxazole C-3-arylations followed by benzisoxazole ring opening gives access to 2-aminobenzophenones in only two steps.