883-39-6

Usage

Uses

Used in Chemical Synthesis:
1-Phenyl-1H-benzotriazole is used as a reagent in the preparation of possible surrogates for Kobayashi's aryne precursors. Its ability to form stable complexes with metal ions allows it to facilitate the synthesis of these precursors, which are important intermediates in organic chemistry for the formation of various complex organic molecules.
Used in Catalysts and Ligands:
Due to its strong affinity for metal ions, 1-Phenyl-1H-benzotriazole is employed as a ligand in the development of homogeneous catalysts. These catalysts are used to accelerate chemical reactions, improving their efficiency and selectivity. The benzotriazole moiety in 1-Phenyl-1H-benzotriazole contributes to the stability and performance of the resulting catalysts.
Used in Corrosion Inhibition:
1-Phenyl-1H-benzotriazole is also utilized as a corrosion inhibitor in various industries, such as the automotive and aerospace sectors. Its ability to form stable complexes with metal ions helps protect metal surfaces from corrosion, extending the lifespan of components and reducing maintenance costs.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Phenyl-1H-benzotriazole is used as a building block for the synthesis of various drug candidates. Its unique chemical properties and reactivity make it a valuable component in the development of new medications with potential therapeutic applications.
Used in Materials Science:
1-Phenyl-1H-benzotriazole is employed in the development of advanced materials, such as organic semiconductors and conductive polymers. Its electronic properties and ability to form stable complexes with metal ions contribute to the performance and stability of these materials, which have potential applications in electronic devices, sensors, and energy storage systems.

InChI:InChI=1/C12H9N3/c1-2-6-10(7-3-1)15-12-9-5-4-8-11(12)13-14-15/h1-9H

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 591-50-4 iodobenzene 
• 429-41-4 tetrabutyl ammonium fluoride 
• 273-02-9 2H-benzo[d][1,2,3]triazole 
• 57601-36-2 2-(3-acetyl-3-methyltriaz-1-en-1-yl)benzoic acid 
• 622-37-7 Phenyl azide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 1610366-30-7 C₈H₁₁N₃O 
• 18773-93-8 1-acetyl-1H-benzotriazole 
• 66003-76-7 Diphenyliodonium triflate 
• 54264-50-5 1-(1H-benzo[d][1,2,3]triazol-1-yl)propan-1-one 
• 30516-21-3 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylethan-1-one 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 6293-66-9 diphenyliodonium p-toluenesulfonate 

Downstream Products

• 86-74-8 9H-carbazole 
• 1444922-88-6 C₃₀H₂₄AuN₃P⁽¹⁺⁾*CF₃O₃S^(1-) 
• 1201669-54-6 N-1-phenyl-benzotriazole-N-3-borane 

Relevant academic research and scientific papers

Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination

The functionalized benzotriazoles are prepared by palladium catalyzed intramolecular amination of 2-bromodiaryltriazene. By screening the reaction conditions, such as ligand, solvent, base and reaction concentration, the optimal reaction conditions were o

Synthetic method of palladium-catalyzed N -aryl benzotriazole derivative

The invention discloses palladium catalysisNA method for synthesizing - arylbenzotriazole derivatives, comprising the steps of reacting under the presence of a palladium catalyst, a ligand and a base, wherein the bromine-substituted aryltriazene is reacte

L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols

A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.

Selective Synthesis of N-H and N-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes

The synthetic utility of NaN3 as the azide component in the [3 + 2] annulation with arynes generated from 2-(trimethylsilyl)aryltriflates resulting in the transition-metal-free synthesis of N-H and N-aryl benzotriazoles has been demonstrated. Using CsF as the fluoride source in CH3CN, the N-H benzotriazoles are formed in high selectivity instead of the expected azidobenzene. Interestingly, N-aryl benzotriazoles are formed using KF and THF as solvent in an open-flask reaction. Moreover, a method for the N1-arylation of benzotriazole is also presented.

Cu-catalyzed arylation of 1-acyl-1H-1,2,3-Benzotriazoles via C–N activation

An efficient copper-catalyzed arylation reaction of 1-acyl-1H-1,2,3-benzotriazoles with diaryliodonium salts via C–N activation is explored. The reaction is conducted regioselectively to form 1-aryl-1H-1,2,3-benzotriazoles in MeCN at 80 °C in the presence of cesium carbonate. 29 examples are given with the product yield of up to 84%. The probable reaction mechanism is proposed.

Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis

The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.

Regioselective N1- or N2-modification of benzotriazoles with iodonium salts in the presence of copper compounds

Modification of benzotriazoles with iodonium salts [diphenyl- and (E)-styrylphenyliodonium tosylates] occurs at the N1-position in the presence of K2CO3 as a base and CuI as a catalyst in CH2Cl2, wher

N, O-Bidentate ligand-tunable copper(II) complexes as a catalyst for Chan-Lam coupling reactions of arylboronic acids with 1 H-imidazole derivatives

An efficient procedure for Chan-Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives using N,O-bidentate ligand-tunable copper(ii) complexes as a catalyst under base-free conditions has been developed. This protocol features mild reac

Triazole derivatives, preparation method thereof and organic electroluminescent element

The invention discloses a 1,2,3-triazole derivative, a preparation method thereof and an organic electroluminescent element. The 1,2,3-triazole derivative is a derivative using 1,2,3-triazolo-1,2a-tetrahydropyridazine as a core structure, and can be used as a luminescent material and a luminescent host material in the organic electroluminescent element.

The Disappearing Director: The Case of Directed N-Arylation via a Removable Hydroxyl Group

A facile and broadly applicable method for the regiospecific N-arylation of benzotriazoles is reported. Copper-mediated reactions of diverse 1-hydroxy-1H-benzotriazoles with aryl boronic acids lead to 1-aryl-1H-benzotriazole 3-oxides. A N1-OH→N3 prototropy in the 1-hydroxy-1H-benzotriazoles is plausibly the underlying basis, where the tautomer is captured by the boronic acid, leading to C?N (not C?O) bond formation. Because the N?O bond in amine N-oxides and 1-hydroxy-1H-benzotriazoles can be easily reduced by diboron reagents such as (pinB)2 and B2(OH)4, exposure of the 1-aryl-1H-benzotriazole 3-oxides to B2(OH)4 then leads to facile reduction of the N?O bond resulting in diverse, regiospecifically-arylated benzotriazoles. Thus, the N-hydroxyl group in 1-hydroxy-1H-benzotriazoles acts as a disposable arylation director. (Figure presented.).