13229-02-2

Basic information

• Product Name: 4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE
• Synonyms: TIMTEC-BB SBB000674;ASISCHEM D13313;BUTTPARK 25\07-91;AKOS TOT-0021;AKOS BBS-00000663;4-AMINO-5-(2-CHLOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL;4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE;2,4-Triazole-3-thiol, 4-amino-5-(o-chlorophenyl)-
• CAS NO: 13229-02-2
• Molecular Formula: C₈H₇ClN₄S
• Molecular Weight: 226.69
• Mol File: 13229-02-2.mol

Chemical Properties

• Boiling Point: 344.9°Cat760mmHg
• Flash Point: 162.4°C
• Appearance: /
• Density: 1.62g/cm³
• Vapor Pressure: 6.38E-05mmHg at 25°C
• Refractive Index: 1.775
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE(13229-02-2)
• EPA Substance Registry System: 4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE(13229-02-2)

Safety Data

• Hazardous Substances Data: 13229-02-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of biologically active molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE is utilized as a building block in the creation of agrochemicals, potentially enhancing crop protection and yield.
Used in Medicinal Chemistry Research:
4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE is employed as a research compound in medicinal chemistry to explore its potential in the development of new drugs and therapies.
Used in Material Science:
In the field of material science, 4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE is used for its potential to contribute to the advancement of new materials with specific properties.
Used in Antimicrobial and Antifungal Applications:
4-AMINO-3-MERCAPTO-5-(2-CHLOROPHENYL)-[1,2,4-]TRIAZOLE is studied for its potential use as an antimicrobial and antifungal agent, given its demonstrated biological activities that could be harnessed in various applications to combat microbial infections.

InChI:InChI=1/C8H7ClN4S/c9-6-4-2-1-3-5(6)7-11-12-8(14)13(7)10/h1-4H,10H2,(H,12,14)

Upstream product

• 75-15-0 carbon disulfide 
• 5814-05-1 2-chlorobenzoylhydrazide 
• 610-96-8 methyl chlorobenzoate 
• 118-91-2 ortho-chlorobenzoic acid 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 68468-96-2 C₈H₆ClN₂OS₂^(1-)*K⁽¹⁺⁾ 
• 2231-57-4 Thiocarbohydrazide 
• 1251851-81-6 C₈H₆ClN₂O₂S^(1-)*K⁽¹⁺⁾ 
• 23766-27-0 2-mercapto-5-(2-chlorophenyl)-1,3,4-oxadiazole 

Downstream Products

• 68469-21-6 3-(2-chloro-phenyl)-5H-[1,2,4]triazolo[3',4':2,3][1,3,4]thiadiazino[5,6-b]quinoxaline 
• 13182-73-5 6-Amino-3-(2-chlorophenyl)-s-triazolo<3,4-b><1,3,4>thiadiazole 
• 108222-55-5 3-[3-(2-Chloro-phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-chromen-2-one 
• 79074-73-0 3-(2-Chloro-phenyl)-6,7-diphenyl-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 79074-17-2 3-(2-Chloro-phenyl)-6,6-dimethyl-6,7-dihydro-4H,5H-9-thia-1,2,3a,4-tetraaza-cyclopenta[b]naphthalen-8-one 
• 1021490-08-3 6-(1-chloro-3,4-dihydronaphth-2-yl)-3-(2-chlorophenyl)-5,6-dihydro-s-triazolo[3,4-b][1,3,4]thiadiazole 
• 1085384-70-8 C₂₅H₂₂Cl₂N₈S₂ 
• 1119751-33-5 1,8-bis[(3-o-chlorophenyl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]octane 
• 1251851-85-0 4-((aminomethylene)-2'-(4''-chlorophenyl)-5'-methoxyindol-3'yl)-3-(2-chlorophenyl)-5-mercapto-1,2,4 triazole 
• 1251851-89-4 4-((aminomethylene)-2'-(4''-bromophenyl)-5'-methoxy indol-3'yl)-3-(2-chlorophenyl)-5-mercapto-1,2,4 triazole 
• 1227681-95-9 C₂₈H₁₄Cl₂N₈S₂ 
• 1251005-95-4 6-(1-adamantyl)-3-(2-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 151297-78-8 3-(2-chlorophenyl)-6-(pyridin-3-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1236055-23-4 3-(2-chlorophenyl)-6-(isoquinolin-1-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 

Relevant articles and documents

Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification

In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. A series of novel triazolyl pyrazole derivatives (10a-y) in which thiol bearing triazole moiety as the zinc binding functional group was introduced to a pyrazole based pharmacophore was synthesized and evaluated as potent and selective inhibitors of h-TNAP over h-NPP1. The biological screening against h-TNAP, h-IAP, h-NPP1 and h-NPP3 showed that many of the synthesized compounds are selective inhibitors of TNAP. Particularly, the compounds 10a-h, 10j, 10m-q, 10u, 10w and 10x displayed high potency and complete selectivity towards h-TNAP over h-NPP1. Compound 10q emerged as a highly potent inhibitor (IC50 = 0.16 μM or 160 nM) against h-TNAP with 127-fold increased inhibition compared to levamisole. On the other hand, compound 10e was found to be most selective inhibitor against the tested APs and NPPs (IC50 = 1.59 ± 0.36 μM). Binding sites architecture analysis, molecular-docking and molecular dynamics simulations (MDS), revealed the basis for h-TNAP and h-IAP ligand selectivity as well as selectivity towards h-TNAP over h-NPP1. These newly discovered inhibitors are believed to represent valuable lead structures to further streamline the generation of candidate compounds to target VC.

Synthesis, structural characterization and biological studies of neodymium(III) and samarium(III) complexes with mercaptotriazole Schiff bases

A series of neodymium(III) and samarium(III) complexes of type [Ln(L)Cl(H2O)3] have been synthesized with Schiff bases (LH2) derived from 3-(phenyl/substituted phenyl)-4-amino-5-mercapto-1,2,4-triazoles and isatin. The str

Efficient Synthesis of Fluorinated [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazoles

Abstract: An efficient synthesis of fluorinated [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives has been achievedby cyclocondensation of 5-substituted 4-amino-1,2,4-triazole-3-thiols withfluoro-substituted aromatic acids using phosphoryl chloride as a cyclizingagent. The synthesized compounds were characterized by spectroscopic techniques,including IR, 1H NMR, and mass spectra.

Design, synthesis and antimicrobial activities of thiouracil derivatives containing triazolo-thiadiazole as SecA inhibitors

A series of novel thiouracil derivatives containing a triazolo-thiadiazole moiety (7a-7l) have been synthesized by structural modifications on a lead SecA inhibitor, 2. All the compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus, and Bacillus subtilis. Compounds 7d and 7g were also tested for their inhibitory activities against SecA ATPase due to their promising antimicrobial activities. The inhibitory activity of compound 7d was found to be higher than that of 2. Molecular docking work suggests that compound 7d might bind at a pocket close to the ATPase ATP-binding domain.

Synthesis and biological evaluation of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives as acetylcholinesterase inhibitors

An efficient protocol for the synthesis of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives starting from the commercially available d-glucosamine hydrochloride is described by reaction of glycosyl isothiocyanate with various aminotriazoles in DMF. Glycosyl isothiocyanate is an important intermediate and synthetic methods are discussed. The acetylcholinesterase inhibitory activity of these compounds was tested by Ellman’s method. It was found that most compounds exhibited over 90% inhibition and they were subsequently evaluated for their IC50values.

Synthesis and biological activities of 3,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives

Twelve novel triazolothiadiazole derivatives were synthesized from 4-amino-5-substituted-4H-1,2,4-triazole-3-thiols with various aromatic carboxylic acids by cyclization in the presence of phosphorous oxychloride. All the newly synthesized compounds were characterized by FTIR, 1H NMR, mass spectroscopy and elemental analysis. The antimicrobial activities of the title compounds were examined by disc diffusion method against Escherichia coli, Staphylococcus aureus, Pyricularia oryzae and Rhizoctnia solani. The bioassay indicated all synthesized triazolothiadiazole derivatives possessed moderate to good antibacterial and antifungal activities against the tested organisms. Especially, compounds 2e and 2k exhibited excellent antibacterial and antifungal activities among these triazolothiadiazole derivatives.

Synthesis, anti-HIV activity and Molecular modeling study of 3-aryl-6-adamantylmethyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole derivatives

A series of novel 3-aryl-6-adamantylmethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 6a-l were synthesized by a simple method with the aim of developing novel HIV non-nucleoside reverse transcriptase inhibitors. All the synthesized compounds were structurally confirmed by spectral analyses. The structure of 6a was unambiguously verified by X-ray structure determination. The synthesized compounds were evaluated for their anti-HIV activity and four analogs displayed moderate inhibitory activity with EC50 values ranging from 10.10 to 12.40 μg mL-1. Molecular docking of 6g with HIV-1 reverse transcriptase was studied to rationalize some structureactivity relationships (SARs).

Facile synthesis of new 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones

The reaction of 2-bromo-1,4-naphthoquinone with 4-amino-5-aryl-4H-1,2,4-triazole-3-thiols in ethanol at 50 °C gave the corresponding 2-[(4-amino-5-aryl-4H-1,2,4-triazol-3-yl)thio]naphthalene-1,4-diones. Their treatment with EtOH/HCl under reflux conditions produced 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones through intramolecular cyclization.

Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors

A series of 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole derivatives were synthesized by nucleophilic substitution reaction of 5-hydroxy-2-chloromethyl -4H-pyran-4-one with 5-substituted-3-mercapto-4-amino-1,2,4-triazole,

Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety

Three series of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety (5a-k, 6a-i, and 7a-i) have been synthesized, characterized and evaluated for their antibacterial activity. Some of these displayed potent antibacterial activity against several Gram-positive and Gram-negative bacterial strains (including multidrug-resistant clinical isolates) with minimum inhibitory concentration (MIC) values in the range of 4-64 μg/mL and minimum bactericidal concentration (MBC) values in the range of 8-256 μg/mL. Compared with previously reported rhodanine derivatives, these compounds exhibited a broad spectrum of antibacterial activity by means of introducing 4-amino-5-aryl-1,2,4-triazole-3-thione moiety. Notably, compound 5f exhibited good antibacterial activity against Staphylococcus aureus RN 4220, S. aureus 209, S. aureus 503, Gram-negative bacteria (Escherichia coli 1924), and Candida albicans 7535 with MBC values of 8 or 16 μg/ml. All of the compounds synthesized in the current Letter were characterized by 1H NMR, 13C NMR, infrared and mass spectroscopy.