1455-92-1

Usage

Uses

Used in Pharmaceutical Industry:
5-(Methylthio)-1-phenyl-1H-1,2,3,4-tetraazole is used as an intermediate in the synthesis of pharmaceuticals for its potential anti-cancer properties, where it inhibits the growth of cancer cells, offering a promising avenue for cancer treatment research.
Used in Agrochemical Industry:
5-(Methylthio)-1-phenyl-1H-1,2,3,4-tetraazole also serves as a building block in the creation of agrochemicals, contributing to the development of products designed to protect crops and enhance agricultural yields.
Used in Dye and Pigment Production:
5-(Methylthio)-1-phenyl-1H-1,2,3,4-tetraazole is utilized in the production of dyes and pigments, capitalizing on its chemical structure to create a range of colorants for various applications.
Used in Neurological Disorder Treatment:
It has been studied for potential applications in the treatment of neurological disorders, suggesting that 5-(Methylthio)-1-phenyl-1H-1,2,3,4-tetraazole may have therapeutic effects on conditions affecting the brain and nervous system.
Used as an Antimicrobial Agent:
5-(Methylthio)-1-phenyl-1H-1,2,3,4-tetraazole is explored for its antimicrobial potential, indicating its use in combating microbial infections and contributing to the field of infectious disease management.

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

Upstream product

• 186581-53-3 diazomethane 
• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 86-93-1 1-phenyl-1H-tetrazole-5-thiol 
• 60-29-7 diethyl ether 
• 74-88-4 methyl iodide 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 77-78-1 dimethyl sulfate 
• 2533-69-9 methyl 2,2,2-trichloroacetimidate 
• 103-72-0 phenyl isothiocyanate 
• 616-38-6 carbonic acid dimethyl ester 
• 20389-38-2 1-Phenyl-5-mercaptotetrazol-Silber 

Downstream Products

• 3206-44-8 5-methanesulfonyl-1-phenyl-1H-tetrazole 
• 94201-87-3 5-Methylsulfanyl-1-(4-nitrophenyl)tetrazole 
• 97990-02-8 Toluene-4-sulfonate2-methyl-5-methylsulfanyl-4-phenyl-4H-tetrazol-2-ium; 
• 97990-06-2 Toluene-4-sulfonate1-methyl-5-methylsulfanyl-4-phenyl-4H-tetrazol-1-ium; 
• 74-93-1 methylthiol 
• 62-53-3 aniline 
• 5533-43-7 5-hydrazinyl-1-phenyl-1H-tetrazole 
• 1618101-38-4 5-[(3,5-dinitrobenzyl)oxy]-1-phenyl-1H-tetrazole 

Relevant academic research and scientific papers

Stereoselective synthesis of Z alkenyl halides via Julia olefination

Julia olefination between α-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereoselectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.

Synthesis of some derivatives of pyrimido[5,4-e]tetrazolo[5,1-c][1,2,4]triazine; a novel heterocyclic system

Several new derivatives of pyrimido[5,4-e]tetrazolo[5,1-c][1,2,4]triazine have been synthesised through the reaction of 5-hydrazinyl-1H-tetrazole with 5-bromo-2,4-dichloro-6-methylpyrimidine in CHCl3 solution at ambient conditions. Further trea

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Ring Expansion Fluorination of Unactivated Cyclopropanes Mediated by a New Monofluoroiodane(III) Reagent

Herein, we report a new strategy for carbon?carbon bond scission and intramolecular ring expansion fluorination of unactivated cyclopropanes, which was accomplished with a new hypervalent fluoroiodane(III) reagent 1. This novel method delivers medicinally relevant 4-fully substituted fluoropiperidines in moderate to high yields with excellent regio- and diastereoselectivity. Reagent 1, which has an N-acetylbenziodazole framework, was readily synthesized via three steps in 76 % overall yield and was characterized by NMR spectroscopy and X-ray crystallography. Owing to the presence of a secondary I???O bonding interaction between the λ3-iodane atom and the carbonyl oxygen of the acetyl group of the N-acetylbenziodazole framework, 1 has excellent stability and can be stored at ambient temperature for 6 months without any detectable decomposition. Density functional theory calculations and experimental studies showed that the reaction proceeds via a carbocation intermediate that readily combines with a fluoride ion to generate the product.

Alkylation of thiols with trichloroacetimidates under neutral conditions

Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

1-Substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their isosteric analogs: A new class of selective antitubercular agents active against drug-susceptible and multidrug-resistant mycobacteria

In this work, a new class of highly potent antituberculosis agents, 1-substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their oxa and selanyl analogs, is described. The minimal inhibitory concentration (MIC) values reached 1 μM (0.36-0.44 μg/mL) against Mycobacterium tuberculosis CNCTC My 331/88 and 0.25-1 μM against six multidrug-resistant clinically isolated strains of M. tuberculosis. The antimycobacterial effects of these compounds were highly specific because they were ineffective against all eight bacterial strains and eight fungal strains studied. Furthermore, these compounds exhibited low in vitro toxicity in four mammalian cell lines (IC50 > 30 μM). We also examined the structure-activity relationships of the compounds, particularly the effects on antimycobacterial activity of the number and position of the nitro groups, the linker between tetrazole and benzyl moieties, and the tetrazole itself. Relatively high variability of substituent R 1 on the tetrazole in the absence of negative effects on antimycobacterial activity allows further structural optimization with respect to toxicity and the ADME properties of the 1-substituted-5-[(3,5-dinitrobenzyl) sulfanyl]-1H-tetrazoles lead compounds.

Regioselective formal hydroamination of styrenes with 1-phenyl-1 H -tetrazole-5-thiol

1-Phenyl-1H-tetrazole-5-thiol 1 (PT-thiol) is employed in a unique Markovnikov-selective formal hydroamination of styrenyl compounds in the presence of catalytic amounts of Ga(OTf)3. This gives rise to the formation of tetrazolothione moieties

Rapid, stable, chemoselective labeling of thiols with Julia- Kocienski-like reagents: A serum-stable alternative to maleimide-based protein conjugation

Exquisite chemoselectivity for cysteine has been found for methylsulfonylphenyloxadiazole compounds under various buffer conditions. Furthermore, the resulting protein conjugates have superior stability to cysteine-maleimide conjugates in human plasma (HS

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.

SH-methylation of SH-containing heterocycles with dimethyl carbonate via phase-transfer catalytic reaction

A reaction of SH-containing heterocycles with dimethyl carbonate (DMC) in the presence of K2CO3 and tetrabutylammonium bromide (Bu4NBr) gave heteroaryl methyl thioethers in 44-93% yields. The reaction was carried out under mild conditions. This method provided a useful synthetic method for preparation of various heteroaryl methyl thioethers without the use of toxic methylic halides or dimethyl sulfate.