2294-47-5

Usage

Uses

1,4-Diazido Benzene is versatile intermediate with a diverse range of applications in organic and bioorganic chemistry, with their use as photoaffinity labeling reagents.

Safety Profile

Explodes violently when heated. When heated to decomposition it emits toxic fumes of NOx. See also AZIDES.

InChI:InChI=1/C6H4N6/c7-11-9-5-1-2-6(4-3-5)10-12-8/h1-4H

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 4612-26-4 1,4-Phenyldiboronic acid 
• 624-38-4 para-diiodobenzene 
• 14860-64-1 4-azidoaniline 
• 106-50-3 1,4-phenylenediamine 
• 7570-09-4 1,4-dihydrazino-benzene 
• 105-12-4 p-dinitrosobenzene 

Downstream Products

• 1296864-26-0 C₁₁H₁₄N₆Si 
• 1314889-24-1 C₂₈H₃₂N₆Si₂ 
• 1314889-23-0 C₂₂H₁₆N₆ 
• 1275593-66-2 2-(1-(4-azidophenyl)-1H-1,2,3-triazol-4-yl)-5-((triisopropylsilyl)ethynyl)pyridine 
• 1275593-56-0 1,4-bis(4-(5-((triisopropylsilyl)ethynyl)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)benzene 
• 1275593-54-8 2-(1-(4-azidophenyl)-1H-1,2,3-triazol-4-yl)-5-ethynylpyridine 
• 1275593-57-1 1,4-bis(1-(4-(4-(5-((triisopropylsilyl)ethynyl)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)benzene 
• 1275593-61-7 2-(1-(4-(4-(3,5-bis(1-(3,5-di-tert-butylphenyl)-1H-1,2,3-triazol-4-yl)phenyl)-1H-1,2,3-triazol-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)-5-((triisopropylsilyl)ethynyl)pyridine 

Relevant academic research and scientific papers

Synthesis, molecular docking, and evaluation of novel bivalent pyrazolinyl-1,2,3-triazoles as potential VEGFR TK inhibitors and anti-cancer agents

Abstract: Investigations in the discovery of tyrosinase enzyme inhibitors have the potential to design novel anti-cancer drugs. A variety of novel bivalent pyrazolinyl triazoles 5–7 were synthesized and identified. The bis-acetyl triazole 3 was accomplish

Click chemistry produces hyper-cross-linked polymers with tetrahedral cores

Methane and adamantane based hyper-cross-linked polymers have been prepared by click chemistry reacting the corresponding tetraalkynes with 1,4-diazidobenzene. The adamantane based HCP proved to be very efficient for CO2 capture at low pressure

New cyclic RGD peptides: Synthesis, characterization, and theoretical activity towards αvβ3 integrin

Two new cyclic RGD peptides were prepared using a click chemistry approach. The linear RGDfV peptide was synthesized by solid-phase peptide synthesis using a 9-fluorenylmetoxicarbonyl (Fmoc) strategy and a 2-chlorotrityl chloride resin. After coupling 5-h

Length-dependent conductance of conjugated molecular wires synthesized by stepwise "click" chemistry

We report the preparation and electrical characterization of conjugated oligophenylenetriazole (OPT) wires having systematically varied lengths up to 10 nm. OPT wires were built from gold substrates using Cu(I)-catalyzed azide alkyne cycloaddition and cha

Bis-ethynylphosphonamidates as an Modular Conjugation Platform to Generate Multi-Functional Protein- and Antibody-Drug-Conjugates

Bis-ethynylphosphonamidates allow for a simple chemoselective addition of two thiol-containing modules in a row. We describe four such bis-electrophiles that carry different functional O-substituents with tunable hydrophilicity and enable further subseque

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.

Linear C2 symmetric compound, lanthanide polynuclear complex and preparation method and application of lanthanide polynuclear complex

The invention discloses a linear C2 symmetric compound, a lanthanide polynuclear complex and a preparation method and application of the lanthanide polynuclear complex, and belongs to the field of photochemical supramolecules. The structural formula of the linear C2 symmetric compound is shown in the specification. The linear C2 symmetric compound is obtained by carrying out triazole cyclization reaction on an azide compound and an alkyne compound at the temperature of 50-70 DEG C. The lanthanide polynuclear complex has a general formula Ln2nL3n, wherein Ln is selected from lanthanide, L is anorganic ligand selected from the linear C2 symmetric compound, and n is selected from 1 or 2. The preparation method comprises the steps: carrying out a reaction on a lanthanide Ln precursor with theorganic ligand L at the temperature of 30-50 DEG C. The linear C2 symmetric compound comprises a triazole-pyridine-amide chelating group, can improve the efficiency of energy transfer from an intermediate chromophore of the ligand to a rare earth center, and improve the construction of a lanthanide complex having a high nuclear number, and thus the obtained complex having strong light-emitting properties and includes a lanthanide organic polyhedral cage having a high nuclear number.

Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts

Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: Exceptional performance of a Cu2O-CuO-Cu-C nanocomposite

A convenient, inexpensive and effective route for the preparation of a Cu2O-CuO-Cu-C nanocomposite is described here by applying Cu(ii) as a source of copper. Characterization of the nanocomposite was performed with X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), high-resolution TEM (HR-TEM), field emission scanning electron microscopy (FE-SEM), X-ray photoelectron spectroscopy (XPS), and energy-dispersive X-ray spectroscopy (EDX). Analysis of the data showed that the particles of the nanocomposite are uniformly distributed and show high catalytic activity in the cross-coupling of sodium azide with various aryl iodides and bromides. This nanocomposite has a high level of performance, and even led to the synthesis of the products at room temperature. In addition, this is the first report of the synthesis of aryl azides under both base- and ligand-free conditions. For the first time, both ligand- and base-free conditions were applied for the synthesis of aryl azides, which implies exceptional performance of the Cu2O-CuO-Cu-C nanocomposite. Simultaneous removal of the base and ligand in a green solvent is the main advantage of this reaction. Unfortunately, aryl bromides and aryl iodides with electron-withdrawing functional groups in their scaffold did not give the desired aryl azides.

Dual role of Cu2O nanocubes as templates and networking catalysts for hollow and microporous Fe-porphyrin networks

Cu2O nanocubes were used for the synthesis of hollow and microporous Fe porphyrin networks (H-MFePN). In this synthesis, Cu2O nanocubes performed not only as networking catalysts but also as shape controlling templates. MFePN were formed on the surface of the Cu2O nanocubes through azide-alkyne cycloaddition of tetrakis(4-ethynylphenyl) Fe-porphyrin with 1,4-diazidobenzene. H-MFePN showed excellent catalytic activities in carbene insertion into N-H bonds, maintaining their activities during five recycle tests.