20939-15-5

Basic information

• Product Name: 4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: 4-AMINO-3-MERCAPTO-5-(METHYL)-[1,2,4]-TRIAZOLE;4-AMINO-3-MERCAPTO-5-METHYL-4H-1,2,4-TRIAZOLE;4-AMINO-5-METHYL-4H-1,2,4-TRIAZOL-3-YL HYDROSULFIDE;4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL;AKOS B009487;AKOS TOT-0007;IFLAB-BB F0820-0406;AURORA 13367
• CAS NO: 20939-15-5
• Molecular Formula: C₃H₆N₄S
• Molecular Weight: 130.17
• Product Categories: THIOL
• Mol File: 20939-15-5.mol

Chemical Properties

• Melting Point: 202-205°C
• Boiling Point: 196.2 °C at 760 mmHg
• Flash Point: 72.4 °C
• Appearance: /
• Density: 1.69 g/cm³
• Vapor Pressure: 0.404mmHg at 25°C
• Refractive Index: 1.803
• CAS DataBase Reference: 4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL(20939-15-5)
• EPA Substance Registry System: 4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL(20939-15-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 20939-15-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL is utilized as a building block for the synthesis of biologically active molecules. Its unique structure allows for the creation of new compounds with potential therapeutic effects.
Used in Antimicrobial and Antifungal Agents:
Due to its inherent antimicrobial and antifungal properties, 4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL is used in the development of new drugs that can combat a range of microbial infections.
Used in Agrochemicals:
4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL's antimicrobial properties also extend to its use in the development of agrochemicals, which can help protect crops from various diseases and pests.
Used in Materials Science:
4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL has potential applications in the production of corrosion inhibitors for metals, which can be used to protect metal surfaces from degradation and extend their service life.
Used in Coatings Industry:
4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL's ability to inhibit corrosion also makes it a valuable component in the development of coatings that can be applied to various surfaces to provide protection against environmental factors that cause wear and tear.

InChI:InChI=1/C3H6N4S/c1-2-5-6-3(8)7(2)4/h4H2,1H3,(H,6,8)

Upstream product

• 20198-75-8 methyl ester of N²-acetyl-dithiocarbazic acid 
• 64-19-7 acetic acid 
• 2231-57-4 Thiocarbohydrazide 
• 141-78-6 ethyl acetate 
• 5469-75-0 (2R,3S,4R,5S)-2,3,4,5-tetraacetoxyhexanedioic acid 
• 64-17-5 ethanol 
• 302-01-2 hydrazine 

Downstream Products

• 75853-95-1 3-methyl-4-benzylideneimino-5-mercapto-1,2,4-triazole 
• 54025-94-4 3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazine 
• 65901-92-0 3-Methyl-4-amino-5-methylmercapto-1,2,4-triazol 
• 43029-40-9 3-methyl-6-phenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole 
• 220090-13-1 3-methyl-4-(4-nitrobenzylidenenitrilo)-4,5-dihydro-1H-1,2,4-triazole-5-thione 
• 90871-40-2 4-Amino-3-benzylthio-5-methyl-4H-1,2,4-triazole 
• 522638-77-3 4-chloro-N-(3-methyl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzamidine 
• 522638-78-4 4-bromo-N-(3-methyl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzamidine 
• 522638-76-2 N-(3-methyl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzamidine 
• 522638-79-5 4-methyl-N-(3-methyl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzamidine 
• 1000608-48-9 [(triphenylphosphine)2 copper(I) (4-amino-5-methyl-2H-1,2,4-triazole-3(4H)-thione)] nitrate*ethanol 
• 552881-02-4 3,6-dimethyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine 
• 22184-43-6 6-(p-methoxyphenyl)-3-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine 
• 1239270-00-8 di-t-butyl 2-(4-amino-5-methyl-4H-1,2,4-triazol-3-yl-sulfanyl)-3-(triphenyl-λ(5)-phosphanylidene)-succinate 

Relevant articles and documents

1,2,4-triazole-3-thione Schiff bases compounds: Crystal structure, hirshfeld surface analysis, DFT studies and biological evaluation

Three novel Schiff base compounds (G1, G2 and G3) were synthesized and characterized by elemental analysis, FT-IR, NMR, and X-ray single crystal diffraction. The crystal structures exhibit both inter- and intra-molecular h

Crystal and Molecular Structures of Mononuclear Coordinated Copper(I) Complexes with Thio-triazole and Thio-triazine based Schiff base Ligands

Reaction of 4-amino-5-methyl-1,2,4-triazol-3(2H)-thione (AMTT) and 4-amino-6-methyl-3-thio-3,4-dihydro-1,2,4-triazin-5(2H)-one (AMTTO) with 2-hydroxybenzaldehyde led to the synthesis of corresponding Schiff base ligands [(Z)-4-((2-hydroxybenzylidene)amino

Synthesis of Novel Triazolyl Thiourea Derivatives and Their Antibacterial Activity

4-Amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized in three steps from carbon disulfide, hydrazine hydrate, and acetic acid. Its reaction with benzoyl isothiocyanates prepared from substituted benzoyl chlorides and ammonium thiocyanate afforded the corresponding N-benzoyl-N′-triazolyl-thioureas. The obtained compounds were screened for antibacterial activity against Staphylococcus aureus (ATCC 25923), Staphylococcus epidermidis (ATCC 12228), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853). Their antibacterial activity against gram-positive bacteria was higher than against gram-negative bacteria, and derivatives containing electron-withdrawing groups were more active than those with electron-donating substituents.

Synthesis and biological evaluation of some novel S-β-D-glucosides of 4-amino-5-alkyl-1,2,4-triazole-3-thiones derivatives

A novel series of 3-S-β-D-glucosides-4-arylideneamino-5-alkyl-1,2,4-triazoles were designed and synthesized by reaction of 4-amino-5-alkyl-4H-1,2,4triazole-3-thiol Schiff bases and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide. The structures of the target compounds have been characterized by 1H NMR, 13C NMR, FT-IR, and Microanalyses. All the newly synthesized compounds have been screened for their in vitro antibacterial and antifungal activities against two Gram-positive bacteria [Bacillus cereus (PTCC 1015) and Staphylococcus aureus (ATCC 25923)], two Gram-negative bacteria [Pseudomonas aeruginosa (ATCC 27853) and Escherichia coli (PTCC 1399) and two fungi [Aspergillus Niger (PTCC 5012) and Candida albicans (PTCC 5027)].

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.

An efficient method for synthesis of some heterocyclic compounds containing 3-iminoisatin and 1,2,4-triazole using Fe3O4 magnetic nanoparticles

1,2,4-triazole derivatives were prepared by reaction of thiocarbohydrazide and some esters in 60% ethanol. Condensation of 1,2,4-triazole derivatives with isatin gave Schiff bases of 3-iminoisatin derivatives. Reaction of malonic or succinic acid dihydraz

Copper metal complex and preparation method and application thereof

The invention discloses a copper metal complex and a preparation method and application thereof. The copper metal complex uses a triazole compound or a thiadiazole compound as a ligand, the active properties of copper ions can be played when the complex is coordinate bonding with the copper metal ions, the copper ions deliver the ligand to the key positions of plants or pests so as to effectively remove pathogenic bacteria and the pests, and the target hitting rate and high efficiency of pesticides are improved. The preparation method includes few steps and is simple in operation but is high in yield and productivity, a large amount of time and cost can be saved in actual production, and economic benefits are good. The copper metal complex has the inhibiting effect on growth and proliferation of early disease bacteria of tomatoes, fusarium oxysporum of cucumbers, fusarium oxysporum of bananas and gloeosporium musarum, and can serve as a pesticide intermediate to be applied to preparation and application of different agricultural fungicides.

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.

Synthesis, characterization, and biological activity of some novel Schiff bases and their Co(II) and Ni(II) complexes: A new route for Co3O4 and NiO nanoparticles for photocatalytic degradation of methylene blue dye

Six novel Co(II) and Ni(II)-triazole Schiff base complexes have been successfully synthesized by refluxing the prepared triazole Schiff bases with CoCl2·6H2O or NiCl2·6H2O. The Schiff base ligands were prepared through condensation of 3-R-4-amino-5-hydrazino-1,2,4-triazole with dibenzoylmethane [R[dbnd]H, CH3, and CH2CH3; namely, L1, L2, and L3, respectively]. The prepared Co(II) and Ni(II) complexes have been identified using elemental analysis, FT-IR, UV–Vis, magnetic moment, conductivity, and thermal analysis. On the basis of the conductance results, it was concluded that all the prepared complexes are nonelectrolytes. Interestingly, the prepared Co(II) and Ni(II) complexes were employed as precursors for producing of Co3O4 and NiO nanoparticles, respectively. The produced nanostructures have been identified by XRD, HR-TEM, FT-IR and UV–Vis spectra. The produced nanoparticles revealed good photocatalytic activity for the degradation of methylene blue dye under UV illumination in presence of hydrogen peroxide. The percent of degradation was estimated to be 55.71% in 420.0?min and 90.43% in 360.0?min for Co3O4 and NiO, respectively. Moreover, the synthesized complexes, nano-sized Co3O4, and NiO products have been examined, employing modified Bauer- Kirby method, for antifungal (Candida albicans and Aspergillus flavus) and antibacterial (Staphylococcus aureus and Escherichia coli) activities.

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.