121649-18-1

Basic information

• Product Name: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE
• Synonyms: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE;5-(4-fluorophenyl)-2,3-dihydro-1,3,4-oxadiazol-2-one
• CAS NO: 121649-18-1
• Molecular Formula: C₈H₅FN₂O₂
• Molecular Weight: 180.1359032
• Mol File: 121649-18-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE(121649-18-1)
• EPA Substance Registry System: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE(121649-18-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 121649-18-1(Hazardous Substances Data)

Usage

Description

5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE is a heterocyclic chemical compound with the molecular formula C8H5FN2O2. It features an oxadiazole ring fused with a 4-fluorophenyl group, which endows it with unique structural and chemical properties. 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE is widely recognized in the field of medicinal chemistry for its potential in the development of pharmaceutical drugs and biologically active molecules.

Uses

Used in Medicinal Chemistry:
5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE is utilized as a key component in the design and synthesis of new pharmaceutical agents due to its diverse biological activities. Its presence in drug molecules can contribute to anti-inflammatory, antimicrobial, and antitumor properties, making it a valuable asset in the development of treatments for various diseases and conditions.
Used in Research as a Biochemical Tool:
In addition to its medicinal applications, 5-(4-fluorophenyl)-1,3,4-oxadiazol-2(3H)-one has been studied for its potential use as a biochemical tool. Its unique structure allows it to interact with biological systems in ways that can be harnessed for research purposes, providing insights into biological processes and the discovery of new therapeutic targets.
Used in Organic Synthesis as a Building Block:
5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE also serves as a versatile building block in organic synthesis. Its reactivity and structural features make it suitable for the creation of more complex organic molecules, which can be applied across various chemical and pharmaceutical industries.
Overall, 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOL-2(3H)-ONE is a multifaceted chemical entity with a broad spectrum of applications in medicinal chemistry, research, and organic synthesis, underscoring its significance in the scientific and pharmaceutical communities.

Upstream product

• 456-06-4 4-fluorobenzoyl hydrazide 
• 541-41-3 chloroformic acid ethyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 595567-05-8 2-(4-fluorobenzene)-1,3,4-oxadiazole 
• 201230-82-2 carbon monoxide 
• 459-57-4 4-fluorobenzaldehyde 
• 1422157-59-2 N′-[chloro-(4-fluorophenyl)methylene]-tert-butylcarbazate 
• 149267-64-1 tert-Butyl-2-[(4-fluorophenyl)methylidene]hydrazinecarboxylate 
• 403-43-0 4-fluorobenzoyl chloride 
• 124-38-9 carbon dioxide 

Downstream Products

• 121649-39-6 N-(3,5-Dioxo-1-phenyl-[1,2,4]triazolidin-4-yl)-4-fluoro-benzamide 
• 121649-31-8 5-(4-Fluoro-phenyl)-2-oxo-[1,3,4]oxadiazole-3-carboxylic acid N-phenyl-N'-[1-phenyl-meth-(E)-ylidene]-hydrazide 

Relevant articles and documents

Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles

An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process features the short reaction time and can be safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggest that the source of CH is from the N-methyl group of DMF. (Figure presented.).

Synthesis of 5-substituted-3H-[1,3,4]-oxadiazol-2-one derivatives: A carbon dioxide route (CDR)

A carbon dioxide route (CDR) for making biologically important 5-substituted-3H-[1,3,4]-oxadiazol-2-ones (SHOs) has been accomplished through synthesis and cyclization of a variety of hydrazides as the key intermediates. All of these hydrazides were prepared readily in 89-97% yields by reacting acid chlorides with a hydrazine monohydrate in the initial step. Then, SHOs were obtained in high yields from hydrazides by reacting them with carbon dioxide under basic conditions. More notable than the high yields, is that the present CDR process for the first time has succeeded in providing a straightforward cyclization reaction leading to SHO formation with simple reagents in ethanol solution.