41421-13-0

Basic information

• Product Name: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE
• Synonyms: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE;5-(4-fluorophenyl)-3H-1,3,4-oxadiazole-2-thione
• CAS NO: 41421-13-0
• Molecular Formula: C₈H₅FN₂OS
• Molecular Weight: 196.2015032
• Mol File: 41421-13-0.mol
• Article Data: 48

Chemical Properties

• Boiling Point: 242.7 °C at 760 mmHg
• Flash Point: 100.6 °C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 0.0334mmHg at 25°C
• Refractive Index: 1.666
• CAS DataBase Reference: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE(41421-13-0)
• EPA Substance Registry System: 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE(41421-13-0)

Safety Data

• Hazardous Substances Data: 41421-13-0(Hazardous Substances Data)

Usage

General Description

5-(4-Fluorophenyl)-1,3,4-oxadiazole-2(3H)-thione is a chemical compound that belongs to the class of oxadiazole derivatives. It is characterized by a 5-membered ring containing an oxadiazole and a sulfur atom. 5-(4-FLUOROPHENYL)-1,3,4-OXADIAZOLE-2(3H)-THIONE has attracted attention due to its potential biological activities, including antimicrobial, antiviral, antifungal, and anticancer properties. Its structure and properties make it a promising candidate for the development of new pharmaceuticals and biologically active molecules. Additionally, 5-(4-Fluorophenyl)-1,3,4-oxadiazole-2(3H)-thione has shown potential as a fluorescent probe for metal ions and as a material for organic light-emitting diodes (OLEDs). Overall, this compound is a versatile building block with diverse applications in the field of medicinal chemistry and material science.

InChI:InChI=1/C8H5FN2OS/c9-6-3-1-5(2-4-6)7-10-11-8(13)12-7/h1-4H,(H,11,13)

Upstream product

• 75-15-0 carbon disulfide 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 456-22-4 4-Fluorobenzoic acid 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 403-33-8 methyl 4-flurobenzoate 
• 61019-29-2 C₈H₆FN₂OS₂^(1-)*K⁽¹⁺⁾ 
• 403-43-0 4-fluorobenzoyl chloride 
• 121-98-2 methyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 3290-99-1 4-methoxybenzoic acid hydrazide 

Downstream Products

• 72385-00-3 3-(4-chloro-anilinomethyl)-5-(4-fluoro-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 72385-18-3 3-[1-(2-chloro-anilino)-ethyl]-5-(4-fluoro-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 72384-41-9 3-[1-(2-ethoxy-anilino)-ethyl]-5-(4-fluoro-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 72385-12-7 3-(diphenylamino-methyl)-5-(4-fluoro-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 124946-14-1 2-(p-nitrobenzylthio)-5-(p-fluorophenyl)-1,3,4-oxadiazole 
• 197371-95-2 2-[5-(4-Fluoro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanylmethyl]-4-methoxy-3,5-dimethyl-pyridine 
• 485334-65-4 [5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-acetic acid 
• 124946-17-4 2-(4-Chloro-benzylsulfanyl)-5-(4-fluoro-phenyl)-[1,3,4]oxadiazole 
• 902806-53-5 4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl 4-fluorobenzoate 
• 1257842-84-4 2-chloro-5-[[(5-(p-fluorophenyl)-1,3,4-oxadiazol-2-yl)thio]methyl]pyridine 
• 1298111-19-9 2-(4-fluorophenyl)-5-(phenylthio)-1,3,4-oxadiazole 
• 1173921-52-2 2-(benzylthio)-5-(4-fluorophenyl)-1,3,4-oxadiazole 
• 459860-95-8 2-(4-fluorophenyl)-5-(ethylthio)-1,3,4-oxadiazole 
• 1356585-75-5 2-(ethylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 1, 3, 4-oxadiazole derivatives as potent neuraminidase inhibitors

Neuraminidase (NA) is an important target in the development of anti-influenza virus drugs. Compounds containing 1,3, 4-oxadiazole heterocycles have good biological activity and have been proved to have wide applications in antibacterial and antiviral drugs. In this paper, a series of novel 1, 3, 4-oxadiazole neuraminidase inhibitors (6a-6l) were designed and synthesized and their inhibitory activities of NA was tested in vitro. The results displayed that compound 6d exerts the best inhibitory activity (IC50 = 0.027 μM), which was obviously lower than that of oseltamivir carboxylate (OSC) (IC50 = 0.082 μM). Molecular docking analysis showed that the 1, 3, 4-oxadiazole heterocycle plays crucial part in compound 6d, and it can interact with the key arginine triad (Arg118, Arg292 and Arg 371) at the NA S1 site. The good efficacy of 6d may also be attributed to the extension of the substituted aniline ring to the 150-cavitiy. The theoretical and experimental results may provide reference for development of new anti-influenza drugs.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents

Abstract: One of the goals of green chemistry is to use environmentally friendly solvents or remove and reduce the volume of harmful spent solvents. In this study, a novel process for the synthesis of 5-substituted 1,3,4-oxadiazole-2-thiol derivatives was proposed via ultrasound-assisted reaction of aryl hydrazides with CS2 (1:1 molar ratio) in some drops of DMF in the absence of basic or acidic catalysts. They were produced in good to excellent yields under easy workup and purification conditions. In order to prove the usefulness of the prepared compounds, their antioxidant, antibacterial, and antifungal potentials were screened by DPPH free radical scavenging, serial twofold microdilution and streak plate methods. Acceptable to significant inhibitory activities were observed with synthesized heterocycles. The results showed that 5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol (3c) is an broad-spectrum antimicrobial agent. Many of them displayed remarkable antioxidant properties comparable to standard controls (ascorbic acid and α-tocopherol). Synthesized 1,3,4-oxadiazoles are also potent candidates to treat cancer, Parkinson, inflammatory, and diabetes diseases. Graphic Abstract: Eighteen 5-substituted 1,3,4-oxadiazole-2-thiol derivatives as potent antimicrobial and antioxidant agents were prepared via a new, efficient and green procedure.[Figure not available: see fulltext.].