93677-89-5

Basic information

• Product Name: 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL
• Synonyms: 4-amino-5-(2,4-dichlorophenyl)-2H-1,2,4-triazole-3-thione
• CAS NO: 93677-89-5
• Molecular Formula: C₈H₆Cl₂N₄S
• Molecular Weight: 261.13
• Mol File: 93677-89-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 368.7°Cat760mmHg
• Flash Point: 176.8°C
• Appearance: /
• Density: 1.75g/cm³
• Vapor Pressure: 1.25E-05mmHg at 25°C
• Refractive Index: 1.787
• CAS DataBase Reference: 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(93677-89-5)
• EPA Substance Registry System: 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL(93677-89-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 93677-89-5(Hazardous Substances Data)

Usage

General Description

4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL is a chemical compound with the molecular formula C9H6Cl2N4S. It is a derivative of the triazole group and contains both amine and thiol functional groups. 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL is commonly used in the pharmaceutical industry for the synthesis of various medications, particularly those targeting microbial infections. It has been studied for its potential antibacterial and antifungal properties. Additionally, 4-AMINO-5-(2,4-DICHLORO-PHENYL)-4H-[1,2,4]TRIAZOLE-3-THIOL is also used in the field of materials science for its ability to function as a building block for the production of various organic compounds and materials.

InChI:InChI=1/C8H6Cl2N4S/c9-4-1-2-5(6(10)3-4)7-12-13-8(15)14(7)11/h1-3H,11H2,(H,13,15)

Upstream product

• 35112-28-8 methyl 2,4-dichlorobenzoate 
• 50-84-0 2,4 dichlorobenzoic acid 
• 2231-57-4 Thiocarbohydrazide 
• 75-15-0 carbon disulfide 
• 5814-06-2 2,4-dichlorobenzohydrazide 
• 56882-52-1 ethyl 2,4-dichlorobenzoate 
• 23288-92-8 2-mercapto-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole 

Downstream Products

• 135220-20-1 2-Butoxy-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-oxide 
• 135220-25-6 2-Butoxy-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 135220-17-6 6-(2,4-Dichloro-phenyl)-2-ethoxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-oxide 
• 128032-42-8 3-(2,4-Dichloro-phenyl)-6-p-tolyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 111827-76-0 3-(2,4-Dichlorophenyl)-6-phenyl-7H-s-triazolo<3,4-b>thiadiazine 
• 128032-45-1 4-[3-(2,4-Dichloro-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl]-phenol 
• 221009-62-7 5-(2,4-dichlorophenyl)-3-mercapto-4-<1'H-2'(3'H)-oxoindol-3'-ylimino>-1,2,4-triazole 
• 862245-69-0 3-(2,4-dichlorophenyl)-6-((4-methoxyphenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 111827-77-1 3-(2,4-Dichlorophenyl)-6-amino-s-triazolo<3,4-b>-1,3,4-thiadiazole 
• 132927-68-5 C₁₆H₁₀Cl₄N₈S₂ 
• 135220-21-2 6-(2,4-Dichloro-phenyl)-2-pentyloxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-oxide 
• 133527-90-9 3-(2,4-dichlorophenyl)-6,7-difuryl-5H-s-triazolo<3,4-b><1,3,4>thiadizine 
• 128032-41-7 3,6-Bis-(2,4-dichloro-phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 135220-26-7 6-(2,4-Dichloro-phenyl)-2-pentyloxy-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 

Relevant articles and documents

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.

Polyethylene glycol mediated, one-pot, three-component synthetic protocol for novel 3-[3-substituted-5-mercapto-1,2,4-triazol-4-yl]-spiro-(indan-1′,2-thiazolidin)-4-ones as new class of potential antimicrobial and antitubercular agents

A series of 3-[3-substituted-5-mercapto-1,2,4-triazol-4-yl]-spiro-(indan-1′,2-thiazolidin)-4-ones 2 were designed for the purpose of searching for novel antimicrobial agents and have been synthesized conveniently in a single step with a three-component protocol in polyethylene (400) as green reaction media. Thus, the condensation reaction between indane-1-one; 4-amino-5-mercapto-1,2,4-triazoles and mercaptoacetic acid in polyethylene glycol (400) gave quantitatively and analytically pure titled compounds 2. The structure of synthesized compound 2 is based on spectral (IR, 1H-NMR, and 13C-NMR) as well elemental analyses. These compounds have been screened for their antibacterial, antifungal, and antitubercular activities. Some of them have showed significant inhibition on fungal and bacterial growth and antitubercular activity against Mycobacterium tuberculosis. The compounds 2a, 2d, and 2e display antifungal activity against Candida albicans [minimum inhibitory concentration (MIC) 3.13, 6.25 μg/mL] and antibacterial activity against Streptococcus pneumoniae (MIC 3.13 μg/mL) of the order of standard drugs tested under similar conditions, and compound 2a showed better antitubercular activity than other compounds against M. tuberculosis (H37Rv strain, MIC 12.5 μg/mL).

Synthesis and antifungal activity of some 3-aryl-8-nitro-1,2,4-triazolobenzothiadiazepines

A number of 3-aryl-8-nitro-1,2,4-triazolobenzothiadiazepines (3) have been synthesized by cyclisation of 4-(2-chloro-5-nitrobenzylideneamino)-5-aryl-3-mercapto-1,2,4-triazoles (2) in pyridine.Their antifungal activity has been screened against Aspergillus niger and Helminthosporium oryzae and compared with that of commercial fungicide Carbendazim tested under similar conditions.