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

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

Downstream Products

• 72385-12-7 3-(diphenylamino-methyl)-5-(4-fluoro-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 197371-95-2 2-[5-(4-Fluoro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanylmethyl]-4-methoxy-3,5-dimethyl-pyridine 
• 124946-17-4 2-(4-Chloro-benzylsulfanyl)-5-(4-fluoro-phenyl)-[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 
• 61019-25-8 4-amino-5-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 

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.

Antibacterial and Antiviral Activities of 1,3,4-Oxadiazole Thioether 4H-Chromen-4-one Derivatives

Various 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives were conceived. The title compounds demonstrated striking inhibitory effects againstXac,Psa, andXoo. EC50data exhibited that A8 (19.7 μg/mL) had better antibacterial activity againstXoothan myricetin, BT, and TC. Simultaneously, the mechanism of action of A8 had been verified by SEM. The results of anti-tobacco mosaic virus indicated that A9 had the bestin vivoantiviral effect compared with ningnanmycin. From the data of MST, it could be seen that A9 (0.003 ± 0.001 μmol/L) exhibited a strong binding capacity, which was far superior to ningnanmycin (2.726 ± 1.301 μmol/L). This study shows that the 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives may become agricultural drugs with great potential.

Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests

To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.