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Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 
• 88617-67-8 N-[4,5-dibromo-2-(p-tolylsulfonylamino)phenyl]-4-methylbenzenesulfonamide 
• 95-54-5 1,2-diamino-benzene 
• 49764-63-8 4,5-dibromo-1,2-diaminobenzene 

Relevant academic research and scientific papers

Synthesis and properties of an unsymmetrical triazole-functionalized (phthalocyaninato)zinc complex

The synthesis of 5,6-dicyano-1H-1,2,3-benzotriazole (2) was significantly simplified and its overall yield was increased. This opens up the possibility for an extended use of 2 as a precursor for triazole-functionalized phthalocyanines. One of them, the unsymmetrical {9,10,16,17,23,24-hexakis(3,5- di-tert-butylphenoxy)[1,2,3]triazolo[4,5-b]phthalocyaninato}-zinc (5) was prepared in a statistical condensation of 2 and 4,5-bis(3,5-di-tert- butylphenoxy)phthalonitrile (3) with subsequent separation by column chromatography. The triazole-functionalized (phthalocyanine)zinc complex 5 shows interesting spectral properties in solutions depending on the chemical medium because of the reactions which are typical for the triazole fragment. These are acid ionization of NH, coordination to metal ions, N-alkylation and N-acylation, among others. Compound 5 was characterized in detail using UV/Vis, 1H and 13C NMR spectroscopy, mass spectrometry (MALDI-TOF), and elemental analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Blue-light-promoted radical C-H azolation of cyclic nitrones enabled by Selectfluor

An original approach to achieve the C(sp2)-H azolation of cyclic aldonitrones mediated by Selectfluor has first been employed. By exploiting a metal-free, visible-light-promoted cross-dehydrogenative C-N coupling reaction between model aldonitrones, 2H-imidazole 1-oxides, and NH-containing azoles, a series of novel azaheterocyclic derivatives have been obtained in yields up to 94%. The elaborated protocol has proved to be appropriate for gram-scale processes and displayed potential for utilization in the synthesis of novel structural analogues of lanabecestat. Besides, mechanistic studies have revealed that this coupling reaction is likely to proceedviaa nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET).

Does the partial molar volume of a solute reflect the free energy of hydrophobic solvation?

Halogenated heterocyclic ligands are widely used as the potent and frequently selective inhibitors of protein kinases. However, the exact contribution of the hydrophobic solvation of a free ligand is rarely accounted for the balance of interactions contributing to the free energy of ligand binding. Herein, we propose a new experimental method based on volumetric data to estimate the hydrophobicity of a ligand. We have tested this approach for a series of ten variously halogenated benzotriazoles, the binding affinity of which to the target protein kinase CK2 was assessed with the use of thermal shift assay. According to the hierarchical clustering procedure, the excess volume, defined as the difference between the experimentally determined partial molar volume and the calculated in silico molecular volume, was found to be distant from any commonly used hydrophobicity descriptors of the ligand. The excess volume, however, properly predicts solute binding affinity. On the way, we have proved that the binding of halogenated benzotriazoles to the protein kinase CK2 is driven mostly by hydrophobic interactions.

CHEMICAL-MECHANICAL POLISHING COMPOSITION COMPRISING BENZOTRIAZOLE DERIVATIVES AS CORROSION INHIBITORS

A chemical-mechanical polishing (CMP) composition is provided comprising (A) one or more compounds selected from the group of benzotriazole derivatives which act as corrosion inhibitors and (B) inorganic particles, organic particles, or a composite or mixture thereof. The invention also relates to the use of certain compounds selected from the group of benzotriazole derivatives as corrosion inhibitors, especially for increasing the selectivity of a chemical mechanical polishing (CMP) composition for the removal of tantalum or tantalum nitride from a substrate for the manufacture of a semiconductor device in the presence of copper on said substrate.

Facile synthesis of benzotriazole derivatives using nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica and two room-temperature nitrite ionic liquids

Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica, 1-butyl-3-methylimidazolium nitrite, and 1-(3-trimethoxysilylpropyl)-3- methylimidazolium nitrite were used as effective reagents for the preparation of benzotriazole derivatives from 1,2-diaminobenzenes at room temperature under mild solvent-free conditions. These ionic liquids play as nitrosonium sources in this procedure.1,2-Diaminobenzene derivatives have been treated with ionic liquids to give the related diaminobenzenes in very good to excellent yields in short reaction times. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the full experimental and spectral details.

Synthesis and physico-chemical properties in aqueous medium of all possible isomeric bromo analogues of benzo-1H-triazole, potential inhibitors of protein kinases

In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2α, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK a values for dissociation of the triazole proton. Experimental data (pKa, solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2α. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.

Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii

Chloro-, bromo- and methyl- analogues of 1H-benzimidazole and 1H-benzotriazole and their N-alkyl derivatives have been synthesized and tested in vitro against the protozoa Acanthamoeba castellanii. The results indicate that 5,6-dimethyl-1H-benzotriazole (11) and 5,6-dibromo-1H-benzotriazole (14) have higher efficacy than the antiprotozoal agent chlorohexidine.