53694-87-4

Usage

Classification

Azidoaromatic compound

Reactivity

High reactivity

Color

White to pale yellow solid

Usage

Reagent in organic synthesis

Applications

Preparation of heterocycles, functionalized aromatic compounds, pharmaceuticals, dyes, and polymers

Safety concerns

Explosive nature and potential health hazards

Environmental impact

Potentially hazardous air pollutant

Handling

Should be managed with care to prevent release into the environment

InChI:InChI=1/C6H4IN3/c7-5-1-3-6(4-2-5)9-10-8/h1-4H

Upstream product

• 7664-41-7 ammonia 
• 624-38-4 para-diiodobenzene 
• 5122-99-6 4-iodophenylboronic acid 
• 540-37-4 p-aminoiodobenzene 

Downstream Products

• 40468-64-2 (4-iodo-phenyl)-(1,2,5-triphenyl-1H-1λ⁵-phosphol-1-ylidene)-amine 
• 84984-19-0 1-(p-iodophenyl)-3-cyanotriazene potassium salt 
• 540-37-4 p-aminoiodobenzene 
• 622-37-7 Phenyl azide 
• 946052-55-7 4-(1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)-N-methylbenzenamine 
• 1009647-34-0 2,6-bis[1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl]-4-(3,6,9-trioxadec-1-yloxy)pyridine 
• 1009647-29-3 2,6-bis[1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl]-4-(3,6,9-trioxadec-1-yloxycarbonyl)pyridine 
• 110684-43-0 1-(4-iodophenyl)-5-phenyl-1H-[1,2,3]-triazole 
• 943154-17-4 4-[(4-azidophenyl)ethynyl]-N,N-bis[4-[(4-azidophenyl)ethynyl]phenyl]-benzenamine 
• 1366497-65-5 (2R,3S,6S)-2-(hydroxymethyl)-6-(1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-3-ol 
• 1366497-42-8 ((2R,3S,6S)-3-acetoxy-6-(1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate 
• 630104-26-6 3,3-diethyl-1-(4-iodophenyl)triaz-1-ene 

Relevant academic research and scientific papers

Synthesis and mesomorphic properties of a new series of triazole bent-core liquid crystalline molecules by "click" reaction

The synthesis and mesomorphic properties of new triazole liquid-crystalline are presented and discussed. These triazole derivatives have been synthesized by reacting 4-hydrazoic iodobenzene with the 4-alkyl phenyl acetylene in dimethyl formamide (DMF). Th

Synthesis of Azidoanilines by the Buchwald-Hartwig Amination

We report a Buchwald-Hartwig amination compatible with azido functionality. Treatment of azidoaryl iodides and amines with fourth-generation Buchwald precatalyst coordinated by CPhos and sodium tert-butoxide in 1,4-dioxane at 50 °C afforded the corresponding azidoanilines while leaving the azido groups intact. The method showed a broad substrate scope and was applicable to the synthesis of diazido compounds as photoaffinity probe candidates of pharmaceutical amines and multiazido platform molecules.

Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides

The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.

Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteaso

Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths

The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.

Facile immobilization of copper(I) acetate on silica: A recyclable and reusable heterogeneous catalyst for azide–alkyne clickable cycloaddition reactions

The structurally well-defined copper(I) acetate was immobilized on silica gel via electrostatic interactions. The catalytic activity of the immobilized catalyst Cu(I)–SiO2 was examined in the click synthesis of 1,2,3-triazoles in water/ethanol

Inhibition of the FAD containing ER oxidoreductin 1 (Ero1) protein by EN-460 as a strategy for treatment of multiple myeloma

Multiple myeloma (MM) cells demonstrate high basal endoplasmic reticulum (ER) stress and are typically exquisitely sensitive to agents such as proteasome inhibitors that activate the unfolded protein response. The flavin adenosine dinucleotide (FAD) conta

Multifunctional Mono-Triazole Derivatives Inhibit Aβ42 Aggregation and Cu2+-Mediated Aβ42 Aggregation and Protect against Aβ42-Induced Cytotoxicity

Amyloid beta (Aβ) peptide aggregation is considered as one of the key hallmarks of Alzheimer's disease (AD). Moreover, Aβ peptide aggregation increases considerably in the presence of metal ions and triggers the generation of reactive oxygen species (ROS)

Thermal azide-Alkene cycloaddition reactions: straightforward multi-gram access to Δ2-1,2,3-Triazolines in deep eutectic solvents

The multi-gram synthesis of a wide range of 1,2,3-Triazolines via azide-Alkene cycloaddition reactions in a Deep Eutectic Solvent (DES) is reported. The role of DES in this transformation as well as the origin of the full product distribution was studied with an experimental/computational-DFT approach.

Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors

Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.