389120-03-0

Basic information

• Product Name: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL
• Synonyms: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL;1,3,4-Oxadiazole-2(3H)-thione, 5-[4-(trifluoroMethyl)phenyl]-;5-[4-(trifluoromethyl)phenyl]-3H-1,3,4-oxadiazole-2-thione
• CAS NO: 389120-03-0
• Molecular Formula: C₉H₅F₃N₂OS
• Molecular Weight: 246.21
• Mol File: 389120-03-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 252.1 °C at 760 mmHg
• Flash Point: 106.3 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 0.0197mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL(389120-03-0)
• EPA Substance Registry System: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL(389120-03-0)

Safety Data

• Hazardous Substances Data: 389120-03-0(Hazardous Substances Data)

Usage

General Description

5-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazole-2-thiol is a chemical compound that belongs to the class of oxadiazoles. It is a heterocyclic compound containing a five-membered ring with oxygen, nitrogen, and sulfur atoms. The trifluoromethyl group and phenyl group in its structure make it a valuable building block for the synthesis of various pharmaceuticals and agrochemicals. 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL has been studied for its potential biological activities, including antimicrobial, antifungal, and antitumor properties. Its unique structural features make it a target for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C9H5F3N2OS/c10-9(11,12)6-3-1-5(2-4-6)7-13-14-8(16)15-7/h1-4H,(H,14,16)

Upstream product

• 75-15-0 carbon disulfide 
• 339-59-3 4-(trifluoromethyl)benzoic acid hydrazide 
• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 

Downstream Products

• 389120-02-9 2-(6,6,5-trifluorohex-5-enylthio)-5-(4-trifluoromethylphenyl)-1,3,4-oxadiazole 
• 1610730-74-9 2-[(8-phenyl-9H-purin-6-yl)thio]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole 
• 1610410-44-0 2-{[6-(4-Fluorophenyl)thieno[3,2-d]pyrimidin-4-yl]thio}-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazole 

Relevant articles and documents

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.].

1, 3, 4-oxadiazole-2 (3H)-thioketone-norfloxacin heterozygote and preparation method and application thereof

The invention discloses a 1, 3, 4-oxadiazole-2 (3H)-thioketone-norfloxacin heterozygote and a preparation method and application thereof, and the structural formula of the 1, 3, 4-oxadiazole-2 (3H)-thioketone-norfloxacin heterozygote is shown as a formula

Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases

The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single molecular architecture. Subsequently, a superior antibacterial compound A6 was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC50 values of 0.734 and 1.79 μg/mL, respectively. These values were better than those of commercial agents bismerthiazol (92.6 μg/mL) and thiodiazole copper (77.0 μg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding minimum EC50 values of 0.295 and 0.607 μg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of scanning electron microscopy, transmission electron microscopy, and fluorescence microscopy images. Given the simple molecular structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of commercial drugs.