34374-67-9

Usage

Uses

Used in Industrial Corrosion Inhibition:
5,6-Dichlorobenzotriazole is used as a corrosion inhibitor for protecting metal surfaces in cooling water systems and engine coolants. It forms a protective film on metal surfaces, preventing corrosion and extending the lifespan of the equipment.
Used in Pharmaceutical and Dye Synthesis:
5,6-Dichlorobenzotriazole is used as an intermediate in the synthesis of pharmaceuticals and dyes, contributing to the development of various products in these industries.
Safety Precautions:
Although 5,6-Dichlorobenzotriazole is considered to have low to moderate toxicity, it is essential to take proper safety precautions when handling it. It can irritate the skin and eyes and may cause respiratory issues if inhaled.

InChI:InChI=1/C6H3Cl2N3/c7-3-1-5-6(2-4(3)8)10-11-9-5/h1-2H,(H,9,10,11)

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 120-82-1 1,2,4-Trichlorobenzene 
• 89-69-0 2,4,5-Trichloronitrobenzene 
• 26280-84-2 5,6-dichloro-1-hydroxy-1H-benzotriazole 
• 6306-39-4 1,2-dichloro-4,5-dinitrobenzene 

Downstream Products

• 72435-62-2 (5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)(phenyl)methanone 
• 1335203-59-2 (E)-2-(5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)-3-p-tolylacrylonitrile 
• 1335203-58-1 (E)-2-(5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)-3-(4-methoxyphenyl)acrylonitrile 
• 128531-10-2 5,6-Dichloro-2-<2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-2H-benzotriazole 
• 128531-14-6 5,6-Dichloro-1-<2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-1H-benzotriazole 

Relevant academic research and scientific papers

A novel bis(pinacolato)diboron-mediated N-O bond deoxygenative route to C6 benzotriazolyl purine nucleoside derivatives

Reaction of amide bonds in t-butyldimethylsilyl-protected inosine, 2′-deoxyinosine, guanosine, 2′-deoxyguanosine, and 2-phenylinosine with commercially available peptide-coupling agents (benzotriazol-1H-yloxy)tris(dimethylaminophosphonium) hexafluorophosphate (BOP), (6-chloro-benzotriazol-1H-yloxy)trispyrrolidinophosphonium hexafluorophosphate (PyClocK), and (7-azabenzotriazol-1H-yloxy)trispyrrolidinophosphonium hexafluorophospate (PyAOP) gave the corresponding O6-(benzotriazol-1-yl) nucleoside analogues containing a C-O-N bond. Upon exposure to bis(pinacolato)diboron and base, the O6-(benzotriazol-1-yl) and O6-(6-chlorobenzotriazol-1-yl) purine nucleoside derivatives obtained from BOP and PyClocK, respectively, underwent N-O bond reduction and C-N bond formation, leading to the corresponding C6 benzotriazolyl purine nucleoside analogues. In contrast, the 7-azabenzotriazolyloxy purine nucleoside derivatives did not undergo efficient deoxygenation, but gave unsymmetrical nucleoside dimers instead. This is consistent with a prior report on the slow reduction of 1-hydroxy-1H-4-aza and 1-hydroxy-1H-7-azabenzotriazoles. Because of the limited number of commercial benzotriazole-based peptide coupling agents, and to show the applicability of the method when such coupling agents are unavailable, 1-hydroxy-1H-5,6-dichlorobenzotriazole was synthesized. Using this compound, silyl-protected inosine and 2′-deoxyinosine were converted to the O6-(5,6-dichlorobenzotriazol-1-yl) derivatives via in situ amide activation with PyBroP. The O6-(5,6-dichlorobenzotriazol-1-yl) purine nucleosides so obtained also underwent smooth reduction to afford the corresponding C6 5,6-dichlorobenzotriazolyl purine nucleoside derivatives. A total of 13 examples were studied with successful reactions occurring in 11 cases (the azabenzotriazole derivatives, mentioned above, being the only unreactive entities). To understand whether these reactions are intra or intermolecular processes, a crossover experiment was conducted. The results of this experiment as well as those from reactions conducted in the absence of bis(pinacolato)diboron and in the presence of water indicate that detachment of the benzotriazoloxy group from the nucleoside likely occurs, followed by reduction, and reattachment of the ensuing benzotriazole, leading to products.

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).

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

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.

Synthesis of benzotriazoles derivatives and their dual potential as α-amylase and α-glucosidase inhibitors in vitro: Structure-activity relationship, molecular docking, and kinetic studies

Benzotriazoles (4–6) were synthesized which were further reacted with different substituted benzoic acids and phenacyl bromides to synthesize benzotriazole derivatives (7–40). The synthetic compounds (7–40) were characterized via different spectroscopic techniques including EI-MS, HREI-MS, 1H-, and 13C NMR. These molecules were examined for their anti-hyperglycemic potential hence were evaluated for α-glucosidase and α-amylase inhibitory activities. All benzotriazoles displayed moderate to good inhibitory activity in the range of IC50 values of 2.00–5.6 and 2.04–5.72 μM against α-glucosidase and α-amylase enzymes, respectively. The synthetic compounds were divided into two categories “A” and “B”, in order to understand the structure-activity relationship. Compounds 25 (IC50 = 2.41 ± 1.31 μM), (IC50 = 2.5 ± 1.21 μM), 36 (IC50 = 2.12 ± 1.35 μM), (IC50 = 2.21 ± 1.08 μM), and 37 (IC50 = 2.00 ± 1.22 μM), (IC50 = 2.04 ± 1.4 μM) with chloro substitution/s at aryl ring were found to be most active against α-glucosidase and α-amylase enzymes. Molecular docking studies on all compounds were performed which revealed that chloro substitutions are playing a pivotal role in the binding interactions. The enzyme inhibition mode was also studied and the kinetic studies revealed that the synthetic molecules have shown competitive mode of inhibition against α-amylase and non-competitive mode of inhibition against α-glucosidase enzyme.

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

Microwave-assisted solid phase diazotation: A method for the environmentally benign synthesis of benzotriazoles

A novel environmentally benign approach based on microwave-assisted solid phase diazotation to convert o-phenylendiamines to substituted benzotriazoles is described. Excellent yields were obtained for a phenylenediamines proving the efficacy of the method. The reaction was carried out in the solid phase under microwave irradiation taking advantage of the strong microwave absorption capability of K-10 montmorillonite that acted as a catalyst and medium in one. The catalyst is recyclable, and the reaction occurs with high efficiency and does not produce any harmful waste.

ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF

The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives of formula (I): wherein R3, R4, R5, R6, R7, P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.

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.

ENANTIOMERICALLY ENRICHED ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF

The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives substantially enriched in an enantiomer of formula (I): and compounds of formula (IH) wherein R3, R4, R5, R6, R7, R13a, R13b, R14a, R14b, P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.