13980-77-3

Usage

Thiol derivative

tetrazole The compound is derived from tetrazole, which is a five-membered aromatic ring containing four nitrogen atoms and one sulfur atom.

Coordination chemistry

ligand 1-P-Tolyl-1H-tetrazole-5-thiol is commonly used as a ligand, a molecule that can donate a pair of electrons to a metal ion to form a coordination complex.

Building block

organic synthesis The compound serves as a building block in the synthesis of other organic compounds, allowing for the creation of more complex molecules.

Unique structure

reactivity The compound's structure contributes to its reactivity, making it useful in a variety of applications.

Industrial applications

pharmaceutical and materials industries 1-P-Tolyl-1H-tetrazole-5-thiol is utilized in both the pharmaceutical and materials industries due to its unique properties.

Biological activities

potential drug development The compound exhibits potential biological activities and has been studied for its possible use in drug development.

Antimicrobial agent

potential applications 1-P-Tolyl-1H-tetrazole-5-thiol has been researched for its potential use as an antimicrobial agent, which could be beneficial in the development of new treatments for infections and diseases.

InChI:InChI=1/C8H8N4S/c1-6-2-4-7(5-3-6)12-8(13)9-10-11-12/h2-5H,1H3,(H,9,11,13)

Upstream product

• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 13078-28-9 5-(p-tolylamino)-1,2,3,4-thiatriazole 
• 106-49-0 p-toluidine 
• 13278-67-6 4-(4-methylphenyl)-3-thiosemicarbazide 
• 43009-17-2 4-methylphenyl dithiocarbamic acid triethylammonium 

Downstream Products

• 78356-17-9 [1-(4-Tolyl)tetrazol-5-ylthio]acetic acid 
• 84079-45-8 acetatohydroxo-1-(p-tolyl)tetrazoline-5-thionatoethylenethioureachromium(III) 
• 14094-61-2 <<1-(4-methylphenyl)-1H-tetrazol-5-yl>thio>-ethyl acetate 
• 154045-96-2 C₂₁H₁₇N₇O₂S 
• 36951-53-8 5-bromo-1-(4-tolyl)-1H-tetrazole 
• 1231978-28-1 5-(1-(4-methylphenyl)-1H-tetrazol-5-ylsulfanylmethyl)-N-β-D-xylopyranosyl-1,3,4-thiadiazol-2-amine 
• 1231978-27-0 5-(1-(4-methylphenyl)-1H-tetrazol-5-ylsulfanylmethyl)-N-β-D-xylopyranosyl-1,3,4-oxadiazol-2-amine 
• 1231978-10-1 5-(1-(4-methylphenyl)-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,4-thiadiazol-2-amine 
• 1231978-09-8 5-(1-(4-methylphenyl)-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,4-oxadiazol-2-amine 
• 1231978-45-2 N'-[N-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)thiocarbamoyl]-2-(1-(4-methylphenyl)-1H-tetrazol-5-ylsulfanyl)acetohydrazide 

Relevant academic research and scientific papers

The novel copper(I) π,σ-complexes with 1-(aryl)-5-(allylthio)-1H-tetrazoles: Synthesis, structure characterization, DFT-calculation and third-order nonlinear optics

The present work is directed toward preparation, structure and optical property characterization of tetrazole-containing Cu(I) compounds. By means of the alternating-current electrochemical technique copper(I) π,σ-compounds with 1-(4-methylphenyl)- (Matht), 1-(3-chloro-4-methylphenyl)- (Chmatht) and 1-[2-(trifluoromethyl)phenyl]- (Tfmatht) 5-(allylthio)-1H-tetrazoles were obtained in a single crystal form and structurally characterized by X-ray diffraction and Raman spectroscopy. Matht and Chmatht ligands, being attached to the Cu(I) through S-allylic C = C-bond and two tetrazole N-atoms, form stable centrosymmetric dimers [Cu2(Matht)2(H2O)2](BF4)2 and [Cu2(Chmatht)2(СlO4)2]. The presence of an electron acceptor trifluoromethyl group promotes formation of the monomeric [Cu(Tfmatht)2]BF4 and [Cu(Tfmatht)(NH2SO3)(MeOH)] compounds. The compounds were investigated by means of Raman spectroscopy, third-order nonlinear optics and DFT calculations.

Is Bismuth Really the "green" Metal? Exploring the Antimicrobial Activity and Cytotoxicity of Organobismuth Thiolate Complexes

Antimicrobial resistance is becoming an ever-increasing threat for human health. Metal complexes and, in particular, those that incorporate bismuth offer an attractive alternative to the typically used organic compounds to which bacteria are often able to develop resistance determinants. Herein we report the synthesis, characterization, and biological evaluation of a series of homo- and heteroleptic bismuth(III) thiolates incorporating either one (BiPh2L), two (BiPhL2), or three (BiL3) sulfur-containing azole ligands where LH = tetrazolethiols or triazolethiols (thiones). Despite bismuth typically being considered a nontoxic heavy metal, we demonstrate that the environment surrounding the metal center has a clear influence on the safety of bismuth-containing complexes. In particular, heteroleptic thiolate complexes (BiPh2L and BiPhL2) display strong antibacterial activity yet are also nonselectively cytotoxic to mammalian cells. Interestingly, the homoleptic thiolate complexes (BiL3) were shown to be completely inactive toward both bacterial and mammalian cells. Further biological analysis of the complexes revealed the first insights into the biological mode of action of these particular bismuth thiolates. Scanning electron microscopy images of methicillin-resistant Staphylococcus aureus (MRSA) cells have revealed that the cell membrane is the likely target site of action for bismuth thiolates against bacterial cells. This points toward a nonspecific mode of action that is likely to contribute to the poor selectivity's demonstrated by the bismuth thiolate complexes in vitro. Uptake studies suggest that reduced cellular uptake could explain the marked difference in activity between the homo- and heteroleptic complexes.

Efficient dye-sensitized solar cells with potential-tunable organic sulfide mediators and graphene-modified carbon counter electrodes

A new class of organic sulfide mediators with programmable redox properties is designed via density functional theory calculations and synthesized for efficient dye-sensitized solar cells (DSCs). Photophysical and electrochemical properties of these mediators derived from systematical functionalization of the framework with electron donating and withdrawing groups (MeO, Me, H, Cl, CF3, and NO2) are investigated. With this new class of organic mediators, the redox potential can be fine-tuned over a 170 mV range, overlapping the conventional I-/I3-couple. Due to the suitable interplay of physical properties and electrochemical characteristics of the mediator involving electron-donating MeO group, the DSCs based on this mediator behave excellently in various kinetic processes such as dye regeneration, electron recombination, and mass transport. Thus, the MeO derivative of the mediator is identified as having the best performance of this series of redox shuttles. As inferred from electrochemical impedance spectroscopy and cyclic voltammetry measurements, the addition of graphene into the normal carbon counter electrode material dramatically improves the apparent catalytic activity of the counter electrode towards the MeO derivative of mediator, resulting in N719 based DSCs showing a promising conversion efficiency of 6.53% under 100 mW·cm-2 simulated sunlight illumination. Copyright

A facile one-pot synthesis of 1-substituted tetrazole-5-thiones and 1-substituted 5-alkyl(aryl)sulfanyltetrazoles from organic isothiocyanates

Treatments of organic isothiocyanates (R-NCS) with NaN3 in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [S=CN4(R)] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1- substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, NaN3, and pyridine in water at room temperature exclusively formed 1- substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

Synthesis of unsymmetrical sulfides derived from tetrazole-5-thiols

A series of unsymmetrical sulfides derived from I-substituted tetrazole-5-thiols was prepared by fusion of the corresponding 1-R-tetrazole-5-thiol sodium salt with 1-R′-5-halotetrazole. The structure was confirmed by 1H NMR and 13C NMR spectra. The target compounds were prepared in 50-80% yields.