54698-60-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid is used as an antifungal agent for its potential to combat various fungal infections. Its triazole-based structure endows it with the ability to inhibit fungal cell growth by targeting essential ergosterol biosynthesis pathways, thereby disrupting the integrity of fungal cell membranes and hindering their proliferation.
Used in Agricultural Industry:
In agriculture, 1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid is used as a crop protectant to prevent fungal diseases that can damage or destroy crops. Its application helps in maintaining crop health and yield, ensuring food security and reducing economic losses due to fungal infestations.
Used in Cosmetics and Personal Care Industry:
1-Benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid is utilized as a preservative in cosmetics and personal care products to prevent the growth of fungi that can cause product spoilage or lead to skin infections. Its incorporation helps in extending the shelf life of these products and ensuring their safety for consumer use.
Used in Textile Industry:
In the textile industry, 1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid is employed as an antimicrobial agent to protect fabrics from fungal contamination. This helps in maintaining the quality and durability of textiles, as well as preventing any potential health hazards associated with fungal growth on clothing or other fabric items.
Overall, 1-benzyl-5-methyl-1H-[1,2,3]triazole-4-carboxylic acid is a versatile compound with a wide range of applications across different industries, primarily due to its antifungal properties and potential to contribute to the prevention and treatment of fungal-related issues.

InChI:InChI=1/C11H11N3O2/c1-8-10(11(15)16)12-13-14(8)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,15,16)

Upstream product

• 590-93-2 2-Butynoic acid 
• 622-79-7 benzyl azide 
• 100-39-0 benzyl bromide 
• 664351-09-1 1-benzyl-5-methyl-1H-1,2,3-triazol-4-carbonyl chloride 
• 133992-58-2 1-benzyl-5-methyl-1H-1,2,3-triazol-4-carboxylic acid ethyl ester 

Downstream Products

• 664351-09-1 1-benzyl-5-methyl-1H-1,2,3-triazol-4-carbonyl chloride 
• 664351-10-4 1-benzyl-5-methyl-4-(N-methyl)carboxamido-1H-1,2,3-triazole 
• 664351-12-6 N,N-diethyl-1-benzyl-4-carboxyamido-5-methyl-1H-1,2,3-triazole 
• 664351-14-8 1-benzyl-4-chloro-6-phenyl-1H-1,2,3-triazol[4,5-c]pyridine 
• 664351-13-7 1-benzyl-6-phenyl-1,5-dihydro-[1,2,3]triazolo[4,5-c]pyridin-4-one 

Relevant academic research and scientific papers

Tri-Substituted Triazole-Enabled C-H Activation of Benzyl and Aryl Amines by Iron Catalysis

The design of trisubstituted triazoles set the stage for proximity-induced iron-catalyzed C-H activation of benzyl and aryl amines with ample scope. Thereby, C-H alkylations and C-H arylations proved viable with high levels of chemo and positional selectivities by means of racemization-free iron catalysis with the reusable triazole being removed in a traceless fashion.

Synthesis of 1,2,3-Triazole Derivatives by Cyclocondensation of Alkyl Azides with Active Methylene Ketones in the System K2CO3/DMSO

Abstract: The reaction of β-keto esters or acetylacetone with alkyl azides in the system K2CO3/DMSO proved to be a convenient method of synthesis of tri- and disubstituted 1-alkyl-1H-1,2,3-triazoles.

Design, synthesis, and fungicidal activities of novel 5-methyl-1H-1,2,3- Trizole-4-carboxyl amide analogues

Succinate dehydrogenase inhibitors (SDHIs) are fungicides with an amide bond widely used to control plant diseases caused by phytopathogenic fungi. Because of broad spectrum activity of new SDHIs, they have attracted wide attention from the research community. A series of structurally novel SDHIs with a bioactive 1,2,3-triazole moiety were designed and synthesized. Bioactivity screening showed that some of designed N-phenethyl-1,2,3-trizole-4-carboxyl amide analogues exhibited good fungicidal activities toward Sclerotinia sclerotiorum and Botrytis cinerea, while some of Nbenzyl- 1,2,3-trizole-4-carboxyl amide analogues exhibited good fungicidal activities toward Phytophthora capsici and Cercospora arachidicola. EC50 value of compound 5d against Cercospora arachidicola (6.6 μg/mL) was lower than that of chlorothalonil (12.3 μg/mL).

Homocoupling of bromotriazole derivatives on metal complex catalysts

Homocoupling of 4-bromo-1,2,3-triazoles upon treatment with stoichiometric amount of bis(pinacolato)diboron on a palladium catalyst gives 4,4-bi-1,2,3-triazoles in up to 95% yields.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMD A receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues

Succinate dehydrogenase inhibitors (SDHIs) are efficient fungicides that are widely used to control plant diseases caused by phytopathogenic fungi, although their effectiveness is undermined by the development of resistance across a range of different fungi. One of the most common structural features of SDHIs is their amide bond. The introduction of greater structural diversity to SDHIs is a promising strategy to delay the onset of resistance. A series of novel SDHIs containing a bioactive 1,2,3-triazole moiety have been designed and synthesized and their fungicidal and insecticidal activities evaluated. The results of these analyses show that most of the newly synthesized 1,2,3-trizole-4-carboxyl amide (ester) analogues exhibit good fungicidal activities, especially towards Sclerotinia sclerotiorum, and a structure-activity relationship study confirmed that the replacement of the amide group with an ester group had little effect on fungicidal activity, which could be provideous in terms of issues and metabolism. 1,6-Dimethyl phenyl was confirmed as the most efficient substituent of the current study when it was placed on both the amide and ester compounds. Interestingly, some of the newly synthesized compounds displayed good insecticidal activities against Culex pipiens pallens. The results of the current study show that these 1,2,3-triazole-4-carboxyl amide and ester analogues represent a new type of SDHI that could be used for the development of novel pesticides.

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

N6-cycloalkyl-2-phenyl-3-deaza-8-azaadenines: a new class of A1 adenosine receptor ligands. A comparison with the corresponding adenines and 8-azaadenines.

Several 9-benzyl-N6-cycloalkyl-2-phenyladenines, 9-benzyl-N6-cycloalkyl-2-phenyl-8-azaadenines and 4-cycloalkylamino-1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridines were prepared and assayed as A1 adenosine receptor ligands. The 1H-1,2,3-triazolo[4,5-