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

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

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

• 124-38-9 carbon dioxide 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 403-43-0 4-fluorobenzoyl chloride 
• 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 

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.).

5-Phenyl-1,3,4-oxadiazol-2(3 H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit

Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-Triazole 7 as an attractive starting point for a structure-based drug design hit-To-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with drug-like chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.

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.).

Palladium-catalyzed oxidative O-H/N-H carbonylation of hydrazides: Access to substituted 1,3,4-oxadiazole-2(3 H)-ones

A novel palladium-catalyzed oxidative annulation reaction for the C-O, C-N bond formations is developed. The intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their

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.

Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl- methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition

The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N′-(chloro-aryl- methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity.