24848-20-2

Basic information

• Product Name: 4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: 4-AMINO-3-MERCAPTO-5-(TRIFLUOROMETHYL)-4H-1,2,4-TRIAZOLE;TIMTEC-BB SBB007038;OTAVA-BB BB0128761231;4-Amino-5-trifluoromethyl-4H-1,2,4-triazole-;4-amino-5-(trifluoromethyl)-2H-1,2,4-triazole-3-thione;AF-399/25039002;BAS 03049476;NSC156613
• CAS NO: 24848-20-2
• Molecular Formula: C₃H₃F₃N₄S
• Molecular Weight: 184.14
• Mol File: 24848-20-2.mol

Chemical Properties

• Boiling Point: 140.5 °C at 760 mmHg
• Flash Point: 38.8 °C
• Appearance: /
• Density: 2 g/cm³
• Vapor Pressure: 6.12mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL(24848-20-2)
• EPA Substance Registry System: 4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL(24848-20-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 24848-20-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL is used as a key intermediate in the synthesis of various pharmaceuticals for its diverse biological activities and potential therapeutic applications.
Used in Medicinal Chemistry Research:
4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL serves as a valuable research tool in medicinal chemistry, aiding in the development of new drugs and understanding the mechanisms of action for existing ones, due to its unique structural features and biological properties.
Used in Drug Discovery:
4-AMINO-5-TRIFLUOROMETHYL-4H-1,2,4-TRIAZOLE-3-THIOL is utilized in drug discovery processes to identify novel therapeutic agents, leveraging its broad spectrum of biological activities and chemical versatility for the design of new pharmaceutical compounds.

InChI:InChI=1/C3H3F3N4S/c4-3(5,6)1-8-9-2(11)10(1)7/h7H2,(H,9,11)

Upstream product

• 2231-57-4 Thiocarbohydrazide 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 43029-47-6 6-benzyl-3-trifluoromethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 86628-14-0 3-Trifluoromethyl-7H-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine 
• 1262222-97-8 6-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1319729-90-2 C₁₂H₈F₃N₇S 
• 459210-90-3 3-(ethylthio)-5-(trifluoromethyl)-4H-1,2,4-triazol-4-amine 

Relevant articles and documents

Synthesis for novel VO(II)- triazole complexes; spectral, analytical characterization and catalytic usage for biodiesel synthesis from waste oil

Novel mono-nuclear VO(II)-traizoles complexes have been synthesized and fully characterized by all possible tools(analytical, spectral and conformational). The neutral tri-dentate mode, was the suggested bonding feature based on comparative IR spectra. Th

New catalytic approach for nano-sized V(IV), Cr(III), Mn(II) and Fe(III)-triazole complexes: detailed spectral, electrochemical and analytical studies

A new series of metal ion complexes from a triazole-Schiff base was synthesized and fully characterized. The tridentate mode of coordination was the only mode of bonding in a 1:1 (M:L) molar ratio. Octahedral geometry was the only structural form proposed for all chelating compounds. This geometry was established based on UV–Vis, magnetic moments and ESR studies. The nanometer feature for all complexes was extracted from SEM images and XRD data. CV electrochemical study over Fe(III) and Mn(II) complexes (examples) displayed a ip,c/ip,a ratio over 1, which points to irreversible electrode couples. TGA and kinetic parameters reflect a best view about the thermal stability of all tested compounds. Molecular modeling was achieved through an advanced program, to optimize the structural forms and estimate significant parameters. All features concluded from all implemented studies orient us towards the best compounds serving in the intended catalytic application. Proceeding from this, Fe(III) and Mn(II) complexes were chosen for their heterogeneous catalytic application, as they can be used without treatment. Moreover, amounts from such complexes were ignited in open air (calcinations) to produce their corresponding oxides, Fe2O3 and MnO2. The synthesized oxides were fully analyzed to establish their chemical formula, as well as extract their morphological characters, which are the main players in the catalytic field. The surface characteristic and particulate sizes show promise in a catalytic role compared to other similar purchased oxides. The original complexes and their synthesized oxides were utilized separately to synthesize biodiesel from waste oils through heterogenous catalytic process. This process was conducted through a comparative study with other referenced methods. The catalytic role of prepared oxides was clearly observed whenever their original complexes did not display catalytic features as desired. Moreover, this comparative study was prolonged versus purchased oxides (Fe2O3 and MnO2) and the differentiation based on reaction yields after verification of physical features. The priorities of synthesized oxides in the catalytic process were impressive and confirm access to the desired goal.

Synthesis of novel 1,2,4-triazoles and triazolo-thiadiazines as anticancer agents

A new series of 7-arylazo-5H-3-(tri uoromethyl)-6-methyl-1,2,4-triazolo-[3,4- b ]-1,3,4-thiadiazines was pre- pared by reaction of 4-amino-3-tri uoromethyl-5-mercapto-1,2,4-triazoles with N -aryl-2-oxo-propane hydrazonoyl chlo- ride in dioxane under re ux

VEGFR2 and hepatocellular carcinoma inhibitory activities of trisubstituted triazole derivatives

The vascular endothelial growth factor receptor 2 (VEGFR2) is considered as a significant target for inhibition in the discovery of novel molecules with anti-proliferative activity. Here, we report the synthesis of novel derivatives of 1,2,4-triazole as potent VEGFR2 inhibitors with anti-HCC activity. The chemical structures of the target triazole derivatives were assured through elemental and spectral analysis. The in vitro anti-VEGFR2 activity of the new compounds was evaluated. Most compounds revealed promising inhibitory activity in comparison to Sorafenib (IC50= 0.088 μM). The triazolothiadiazine derivative 7a was the most active one (IC50= 0.057 μM). Also, the phenylhydrazono triazole derivatives 11c, 13b, and 13c showed potent activities (IC50= 0.074–0.124 μM) that were comparable to that of Sorafenib. Moreover, the anti-proliferative activity of most active compounds was assessed against two HCC cell lines and against normal hepatic cells THLE3. Compound 7a showed superior activity to Sorafenib; 2 times its activity against HepG2 and 15.5 times against Huh7. Furthermore, compound 13c was comparable to sorafenib against HepG2 and 4.1 times against Huh7. Besides, these potent compounds displayed higher safety profiles than Sorafenib against the normal THLE3 cells. In addition, docking simulation demonstrated good fitting with strong binding interactions within the VEGFR2 ATP binding site. In silico ADME calculations showed good GI absorption and high oral bioavailability of compound 7a.

Synthesis and Biological Evaluation of 1,2,4-Triazole Thioethers as Both Potential Virulence Factor Inhibitors against Plant Bacterial Diseases and Agricultural Antiviral Agents against Tobacco Mosaic Virus Infections

Targeting the virulence factors of phytopathogenic bacteria is an innovative strategy for alleviating or eliminating the pathogenicity and rapid outbreak of plant microbial diseases. Therefore, several types of 1,2,4-triazole thioethers bearing an amide l

Synthesis of Novel 1,2,4-Triazole-3-thione Derivatives as Influenza Neuraminidase Inhibitors

A series of 1,2,4-triazole-3-thione derivatives (6a–6t) were synthesized and evaluated against influenza viruses (H1N1) neuraminidase (NA) in vitro. Eighteen compounds exhibited inhibitory potency with IC50 values ranging from 14.68?±?0.49 to 39.85?±?4.23?μg/mL. Among them, compounds 6e and 6h showed significant inhibitory activity with IC50 values of 14.97?±?0.70 and 14.68?±?0.49?μg/mL, respectively. Structure activity relationships were established. Molecular docking studies were performed to understand the binding interaction between active compounds and NA.

Synthesis and biological activity of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives

A series of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives have been conveniently synthesized via Mannich reaction in good yields. Their structures were identified by IR,1H NMR,13C NMR, and elemental analysis. The preliminary bioassays showed that among 14 new compounds, the trifluoromethyl-containing compounds exhibited superior activity than the methyl-containing ones; some of the compounds displayed significant in vitro and in vivo fungicidal activity against several plant fungi and were comparable with the control Triadimefon; several compounds exhibited certain herbicidal activity against Brassica campestris; several compounds possessed favorable KARI inhibitory activity, especially 8D could be a promising KARI inhibitor for further study. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic Mannich base structures containing piperazine moiety.

1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases

Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.

Synthesis and Fungicidal Activities of Novel 1,2,4-Triazole Thione Derivatives Containing 1,2,3-Triazole and Substituted Piperazine Moieties

A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR, 1H NMR, 13C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative 9g showed broad activities and could be made further structural optimization for novel fungicides innovation research.

Synthesis and biological activities of novel 1,2,4-triazole thiones and bis(1,2,4-triazole thiones) containing phenylpyrazole and piperazine moieties

A series of novel 1,2,4-triazole thione and bis(1,2,4-triazole thione) derivatives containing phenylpyrazole and substituted piperazine moieties have been conveniently synthesized via Mannich reaction using various 1,2,4-triazole thiols, substituted piperazines, and formaldehyde at room temperature in short time. Their structures were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays for 27 new title compounds have shown that some of them possess certain herbicidal activities against Echinochloa crusgalli at 100 μg/mL concentration. Some of the compounds exhibited significant in vitro fungicidal activities, especially against Cercospora arachidicola and Rhizoctonia cerealis at the concentration of 50 μg/mL, and were comparable with that of control Triadimefon. Meanwhile, IXp held the control efficacy of 60% against Puccinia sorghi Schw. at 200 μg/mL concentration in the in vivo test. The SAR analysis has indicated that compounds with two CF3 groups both on triazole and pyrazole rings are more effective than compounds with one CF3 group or two CH3 groups according to their fungicidal activity data. On the whole, compounds VIIIg, IXi, IXo and IXp could be used as novel lead structures for the design and discovery of new fungicides.