81265-86-3

Usage

Classification

Benzonitriles, which are organic compounds that contain a cyano group (C≡N) attached to a benzene ring.

Physical appearance

White to light tan solid, which describes the color and form of the compound.

Uses

Commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals, indicating its importance in the production of these products.

Therapeutic potential

Has been studied for its potential therapeutic applications, including its anti-cancer and anti-inflammatory properties, which suggests its potential as a treatment for certain diseases.

Unique molecular structure

The compound has a distinct molecular structure that makes it of interest in pharmaceutical research and development, which could lead to the discovery of new drugs with improved properties.

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 1885-29-6 anthranilic acid nitrile 
• 251982-44-2 2-(2-nitrobenzylamino)benzonitrile 
• 271-44-3 benzimidazole 
• 394-47-8 2-fluorobenzonitrile 
• 873-32-5 2-Chlorobenzonitrile 
• 2042-37-7 o-cyanobromobenzene 
• 3682-71-1 2-phenyl-2H-indazole 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 3958-60-9 2-nitrophenylmethyl bromide 

Relevant academic research and scientific papers

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Rh(III)-Catalyzed C-H Cyanation of 2 H-Indazole with N-Cyano- N-phenyl- p-toluenesulfonamide

A Rh(III)-catalyzed direct cyanation of 2H-indazoles with N-cyano-N-phenyl-p-toluenesulfonamide has been realized via a chelation-assisted strategy. The methodology enables regioselective access to various ortho-cyanated phenylindazoles in good yields with a broad substrate scope and good functional group compatibility. The obtained cyanated indazoles could further be converted into other value-added chemicals. Importantly, the current protocol is featured with several characteristics, including a novel cyanating agent, good regioselectivity, and operational convenience.

A General One-Pot Synthesis of 2H-Indazoles Using an Organophosphorus–Silane System

A simple and direct approach for the regioselective construction of the privileged 2H-indazole scaffold is described. The developed one-pot strategy involves phospholene-mediated N?N bond formation to access 2H-indazoles. The amount of organophosphorus reagent was minimized by recycling the phospholene oxide with organosilane reductants. Starting from functionalized 2-nitrobenzaldehydes and primary amines, a mild reductive cyclization, involving the use of commercially available phospholene oxide and silanes, delivered a wide variety of substituted 2H-indazoles in good to excellent yields.

Gold modified zeolite: An efficient heterogeneous catalyst for n-arylation of indazole

We herein report N-arylation of indazole with aryl halides using gold modified zeolites (Au-zeolites) as an efficient catalytic system. Au-zeolites with three different gold loading were prepared by ion-exchange method and characterized by UV-visible diffuse reflectance spectroscopy (UV-DRS), transmission electron microscopy and energy-dispersive X-ray spectroscopy (TEM-EDX) and X-ray photoelectron spectroscopy (XPS). The Brunauer-Emmett-Teller (BET) and Langmuir surface areas of the prepared Au(5)-zeolite catalyst were found to be 644 and 929 m2g-1 respectively. Goldmodified zeolites performed as an efficient catalytic system for N-arylation of indazole using diverse aryl halides afforded N1 arylated products in appreciable yield under mild reaction conditions. The catalyst was reusable for at least five times with only a marginal loss of activity. This simple, effective and environmentally benign heterogeneous protocol provides a safer alternative to hazardous, corrosive and more polluting conventional catalysts.

Synthesis and electrochemical behaviour of 2-N-substituted indazoles

A new 2-N-aryl-3-methoxycarbonylindazole synthesis from the 6 F mol-1 reduction of appropriately substituted aryl-nitrones has been developed. The indazoles bearing an electron withdrawing group in the 2-position are electroreducible compounds at high negative potentials producing selectively the corresponding 2-N-substituted indazolines in aqueous alcoholic medium. The nitrile and ester groups are not reduced under the reaction conditions. Three new 2-N-arylindazolines were synthesized and characterized. A second electron withdrawing group attached at the 3-position leads to a less cathodic reduction of the 2-N-aryl-3-methoxycarbonylindazole. An appropriately substituted indazoline was used to generate in situ a new tetracyclic heterocycle.