149440-45-9

Basic information

• Product Name: 2,1,3-BENZOXADIAZOLE, 5-FLUORO-
• Synonyms: 2,1,3-BENZOXADIAZOLE, 5-FLUORO-
• CAS NO: 149440-45-9
• Molecular Formula: C6H3FN2O
• Molecular Weight: 138.1
• Mol File: 149440-45-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,1,3-BENZOXADIAZOLE, 5-FLUORO-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,1,3-BENZOXADIAZOLE, 5-FLUORO-(149440-45-9)
• EPA Substance Registry System: 2,1,3-BENZOXADIAZOLE, 5-FLUORO-(149440-45-9)

Safety Data

• Hazardous Substances Data: 149440-45-9(Hazardous Substances Data)

Usage

Chemical structure

A heterocyclic organic compound consisting of a benzene ring fused to an oxadiazole ring and substituted with a fluorine atom at the 5-position.

Optical properties

Unique optical properties, including high quantum yield, high photostability, and large Stokes shift, making it suitable as a fluorescent probe in biological and chemical research.

Potential applications

5-fluoro-2,1,3-benzoxadiazole has shown potential as a building block for the development of novel materials and pharmaceuticals.

Versatility

The compound's versatile nature and desirable properties make it valuable in various fields of science and industry.

Upstream product

• 2369-11-1 5-fluoro-2-nitroaniline 
• 364-78-3 2-nitro-4-fluoroaniline 
• 36389-16-9 5-Fluorobenzofuroxan 
• 41153-84-8 5-fluoro-2,1,3-benzoxadiazole N³-oxide 

Downstream Products

• 6124-22-7 5-Dimethylamino-benzofurazan 

Relevant articles and documents

Photophysical study of 5-substituted benzofurazan compounds as fluorogenic probes

Nine 5-substituted benzofurazans including the non-substituted benzofurazan were synthesized, and measurements of the fluorescence, photolysis, transient absorption, and time-resolved thermal lensing signal were performed in order to understand the relaxation processes of these compounds. The results indicated that the main relaxation process was a photoreaction from an excited singlet state and the rate of the primary bond cleavage in the excited state tended to increase in the compound in which the S2←S0 absorption band is located close to the S1←S0 absorption band. These results suggest that the reactive state might be the S2 state, and that the interaction between the S1 and S2 states promotes the photoreaction. The separation of the S1 state from the S2 state decreases the rate of photoreaction, resulting in an increase in the Φf values. The Φf values of the 5-substituted benzofurazans in cyclohexane and acetonitrile were compared with their ΔE(S1, S2) (energy gap between the S1 and S2 states) values calculated by using a combination of AM1(EXCITED) and AM1-CAS/ CI(CI = 6) for geometric optimization and calculation of the energy levels, respectively. The ΔE(S1, S2) values correlated well with the Φf values in each solvent, thus enabling us to predict the fluorescence properties of the 5-substituted benzofurazans based on their chemical structures.

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

Studies on aromatase inhibitors IV. Synthesis and biological evaluation of N,N-disubstituted-5-aminopyramidine derivatives

In order to study the potency of the 5-aminopyrimidine skeleton as an aromatase inhibitor, we synthesized various N,N-disubstituted-15- aminopyrimidine derivatives and evaluated their aromatase-inhibitory activity (in vitro) and their inhibitory activity