2851-08-3

Usage

Uses

Used in Rubber Industry:
2-piperidinobenzothiazole is used as an accelerator in the vulcanization process for enhancing the curing of rubber products. It promotes cross-linking between polymer chains, which speeds up the production of rubber items and improves their overall quality.
Used in Pharmaceutical Production:
In the pharmaceutical sector, 2-piperidinobenzothiazole serves as a crucial component in the synthesis of various drugs. Its unique chemical structure allows it to be incorporated into medicinal compounds, contributing to the development of new therapeutic agents.
Used in Agrochemical Production:
Similarly, in agrochemicals, 2-piperidinobenzothiazole is employed in the manufacturing process of different agricultural chemicals. Its properties make it suitable for use in products designed to protect crops and enhance agricultural productivity.

InChI:InChI=1/C12H14N2S/c1-4-8-14(9-5-1)12-13-10-6-2-3-7-11(10)15-12/h2-3,6-7H,1,4-5,8-9H2

Upstream product

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• 2762-59-6 N-phenylpiperidine-1-carbothioamide 
• 2740-81-0 2-chlorophenylisothiocyanate 
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• 98041-44-2 2-iodophenyl isothiocyanate 
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• 10113-39-0 N-formyl-2-iodoaniline 

Relevant academic research and scientific papers

Copper-Catalyzed Electrophilic Amination of Heteroarenes via C-H Alumination

A highly efficient Cu-catalyzed electrophilic amination reaction of readily available heteroarenes with O-benzoyl hydroxylamines via a one-pot C-H alumination is reported. The reactions were catalyzed using 1 mol % of CuCl to afford various heteroaryl amines in good to excellent yields. The direct C-H lithiation/transalumination of heteroarenes and catalytic amination sequence can be performed in a single vessel on gram scales.

Palladium catalyzed amination of 2-chloro-1,3-azole derivatives: Mild entry to potent H1- antihistaminic norastemizole

Palladium-catalyzed selective amination of 4-fluorobenzyl-2-chlorobenzimidazole with 4-aminopiperidine provided a simple solution for the norastemizole synthesis. Pd-catalyzed amination of other 2-chloro-1,3-Azole derivatives are exploited.

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

Copper(ii) ions supported on functionalized graphene oxide: an organometallic nanocatalyst for oxidative amination of azolesviaC-H/C-N bond activation

Graphene oxide (GO) was chemically modified withpara-aminobenzoic acid (PABA) to immobilize copper(ii) ions on its surface and used as a nanocatalyst for the oxidative C(sp2)-H bond amination reaction. A practical method to prepare Cu2+supported onpara-aminobenzoic acid grafted on GO was reported. The prepared Cu2+@GO/PABA was characterized by FT-IR, XRD, SEM, AFM, TEM, UV-Vis, and ICP techniques. The results showed that the morphology, distribution, and loading of copper ions could be well-adjusted by grafting of PABA on GO. Moreover, just 2 mol% of Cu2+@GO-PABA could catalyze the C-H activation reaction of benzoxazole and benzothiazole with secondary amines in >94% yields. Also, the catalyst showed very good recyclability and much less leaching of the Cu into the reaction solution. The high activity of Cu2+@GO-PABA can be ascribed to the good synergistic effects of Cu2+andpara-aminobenzoic acid grafted on graphene oxide.

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

N-Iodosuccinimide mediated intramolecular oxidative C(sp 2)-S bond formation for the synthesis of 2-aminobenzothiazole derivatives

An extremely efficient synthetic method for the preparation of 2-aminobenzothiazole derivatives starting from arylthioureas by using N-iodosuccinimide has been reported. This protocol features a mild reaction conditions, a short reaction time, and metal-free oxidative conditions for C (sp 2)-S bond construction.

HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

Dioxygen-triggered oxidative cleavage of the C-S bond towards C-N bond formation

Research on the cleavage of C-C bonds has been well developed. By comparison with this, the activation of C-S bonds remains challenging. Herein, dioxygen-triggered oxidative cleavage of C-S bonds has been achieved, delivering a series of N-containing heterocyclic compounds that are frequently found in pesticides and pharmaceuticals. Additionally, the potential utility of this protocol was further demonstrated by a gram-scale experiment. Mechanistically, dioxygen plays a key role in the cleavage of C-S bonds towards C-N bond formation.

Solid Supported Nano Structured Cu-Catalyst for Solvent/Ligand Free C2 Amination of Azoles

Ligand- and solvent-free catalytic conditions that harness a nanostructured–CuI catalyst encapsulated in TiO2 has been reported for C2-amination of azoles (benzothiazole, benzoxazole and thiazole). The reaction is highly regioselective. The catalyst is robust, inexpensive and can be recycled up to four times. This strategy was further used for the synthesis of a small molecule with anti-HIV and anti-tumor properties.

Electrochemical intramolecular dehydrogenative C-S bond formation for the synthesis of benzothiazoles

An external oxidant-free intramolecular dehydrogenative C-S cross-coupling has been developed under undivided electrolytic conditions. Various 2-aminobenzothiazoles could be synthesized with up to 99% yield from the direct combination of aryl isothiocyanates with amines. In the presence of a base, this reaction protocol is also applicable for the synthesis of benzothiazoles from N-aryl thioamides.