66536-70-7

Usage

Cyclic organic compound

A compound consisting of a closed ring of organic elements, in this case, carbon and hydrogen.

Triazole ring

A five-membered heterocyclic ring containing three nitrogen atoms, which contributes to the compound's chemical structure and properties.

Corrosion inhibitor

1-Cyclohexyl-1H-benzo[d][1,2,3]triazole is commonly used to protect metals, particularly copper and its alloys, from corrosion by forming a protective film on the metal surface.

Stabilizer in plastics and polymers

The compound is used to protect plastics and polymers from degradation caused by exposure to UV light and heat, thus extending their lifespan and maintaining their properties.

Potential applications in pharmaceuticals

1-Cyclohexyl-1H-benzo[d][1,2,3]triazole may have uses in the development of drugs due to its unique chemical structure and properties.

Potential applications in agrochemicals

The compound may also be utilized in the development of agrochemicals, such as pesticides and fertilizers, due to its ability to provide protection and stabilization.

Industrial and commercial applications

1-Cyclohexyl-1H-benzo[d][1,2,3]triazole has a range of uses in various industries, including metal protection, plastics, and polymers, as well as potential uses in pharmaceuticals and agrochemicals.

Upstream product

• 74628-31-2 N-1-cyclohexylbenzene-1,2-diamine 
• 108-85-0 1-bromocyclohexane 
• 95-14-7 1,2,3-Benzotriazole 
• 110-83-8 cyclohexene 
• 6373-71-3 N-cyclohexyl-2-nitroaniline 
• 108-94-1 cyclohexanone 
• 88-74-4 2-nitro-aniline 
• 110-82-7 cyclohexane 
• 98-89-5 Cyclohexanecarboxylic acid 
• 1365271-85-7 1-cyclohexyl-6-fluoro-1H-benzo[d][1,2,3]triazole 

Downstream Products

• 86-74-8 9H-carbazole 
• 122-39-4 diphenylamine 

Relevant academic research and scientific papers

Copper(II)-Photocatalyzed N-H Alkylation with Alkanes

We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.

Palladium catalyzed hydrodefluorination of fluoro-(hetero)arenes

Palladium catalyzed hydrodefluorination was developed for fine-tuning the properties of fluoro-(hetero)aromatic compounds. The robust reaction can be set up in air, requires only commercially available components, and tolerates a variety of heterocycles and functionalities relevant to drug discovery. Given the prevalence of fluorine incorporation around metabolic hotspots, the corresponding deuterodefluorination reaction may prove useful for converting fluorinated libraries to deuterated analogues to suppress the oxidative metabolism by kinetic isotope effects.

Decarboxylative sp 3 C-N coupling via dual copper and photoredox catalysis

Over the past three decades, considerable progress has been made in the development of methods to construct sp 2 carbon-nitrogen (C-N) bonds using palladium, copper or nickel catalysis 1,2 . However, the incorporation of alkyl substrates to form sp 3 C-N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge. This cross-coupling system uses naturally abundant alkyl carboxylic acids and commercially available nitrogen nucleophiles as coupling partners. It is applicable to a wide variety of primary, secondary and tertiary alkyl carboxylic acids (through iodonium activation), as well as a vast array of nitrogen nucleophiles: nitrogen heterocycles, amides, sulfonamides and anilines can undergo C-N coupling to provide N-alkyl products in good to excellent efficiency, at room temperature and on short timescales (five minutes to one hour). We demonstrate that this C-N coupling protocol proceeds with high regioselectivity using substrates that contain several amine groups, and can also be applied to complex drug molecules, enabling the rapid construction of molecular complexity and the late-stage functionalization of bioactive pharmaceuticals.

Copper-Catalyzed Oxidative Dehydrogenative C(sp3)?H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources

A copper-catalyzed oxidative C(sp3)?H/N?H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)?N bond formation through a radical pathway generated by homolytic cleavage of di-tert-butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerates a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile, methyl, and methoxy. free-NH-containing indoles, pyrroles, pyrazoles, indazoles, and benzotriazoles are successfully N-alkylated.

Synthesis of 1H-benzotriazoles via reductive amination on solid supports

An efficient synthesis of N-benzyl-1H-benzotriazoles utilizing a two-step reductive amination reaction on solid supports has been achieved. The method is suitable for combinatorial synthesis. Georg Thieme Verlag Stuttgart.

The first examples of the addition of heterocyclic NH to unactivated olefins

Benzotriazole adds to aliphatic open-chain and cyclic alkenes at 80 deg C under toluene-p-sulfonic acid catalysis.Terminal aliphatic olefins give solely 2-(benzotriazol-1- and -2-yl)alkanes, which are stable to acid.In the presence of an excess of acid, all possible non-terminal benzotriazol-1- and -2-yl addition products are obtained, owing to a facile migration of the double bond in the starting olefin.Addition also occurs to phenylalkenes with the intervention of some bond migration.