108842-69-9

Basic information

• Product Name: 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid
• Synonyms: 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid
• CAS NO: 108842-69-9
• Molecular Formula: C₁₆H₁₃N₃O₂
• Molecular Weight: 279.29332
• Mol File: 108842-69-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid(108842-69-9)
• EPA Substance Registry System: 1-benzyl-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid(108842-69-9)

Safety Data

• Hazardous Substances Data: 108842-69-9(Hazardous Substances Data)

Usage

Chemical class

Triazole carboxylic acids

Biological activities

Antitumor, antifungal, and antiviral

Application

Building block in the synthesis of pharmaceuticals and agrochemicals

Pharmacological properties

Potent

Structural properties

Unique, attractive for development of new chemical entities

Therapeutic applications

Potential for development of new drugs

Upstream product

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 622-79-7 benzyl azide 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 637-44-5 phenylpropyolic acid 

Downstream Products

• 51118-27-5 1-benzyl-5-phenyl-1H-1,2,3-triazole 
• 108878-81-5 1,3-diethyl-4-phenyl-1,2,3-triazolium iodide 
• 111091-83-9 1-ethyl-3-benzyl-4-phenyl-[1,2,3]triazolium; iodide 

Relevant articles and documents

Palladium-catalyzed aerobic oxidative C-H olefination with removable 1,2,3-triazole directing group

Ortho-olefination of arenes was achieved with removable 1,2,3-triazole auxiliary through Pd-catalyzed C-H activation. Excellent yields were received even when molecular O2 (1 atm) was used as the terminal oxidant. Other heterocyclic directing groups, such as pyridine and quinoline, gave poor reactivity under this aerobic oxidative condition, which highlighted the unique reactivity of triazole in promoting directed C-H activation.

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.

Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group

A palladium(II)-catalyzed regioselective syn-hydroarylation reaction of homopropargyl amines has been developed, wherein selectivity is controlled by a cleavable bidentate directing group. Under the optimized reaction conditions, both dialkyl and alkylaryl alkyne substrates were found to undergo hydroarylation with high selectivity. The products of this reaction contain a 4,4-disubstituted homoallylic amine motif that is commonly seen in drug molecules and other bioactive compounds.

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.