121358-86-9

Usage

Uses

Used in Pharmaceutical Research:
1-Benzyl-1H-pyrazole-4-carbonitrile is used as a building block for the synthesis of compounds with potential pharmacological activity, serving as a crucial component in the development of new drugs.
Used in Neuroscience Research:
In the field of neuroscience, 1-benzyl-1H-pyrazole-4-carbonitrile is used as a drug candidate for exploring its effects on neurological conditions and disorders, given its potential interaction with neural pathways and receptors.
Used in Cancer Research:
1-Benzyl-1H-pyrazole-4-carbonitrile is employed as a potential anti-cancer agent, being studied for its capacity to target and affect cancer cells, with the aim of contributing to the development of novel therapeutic strategies against various types of cancer.
Used in Pest Control Industry:
1-BENZYL-1H-PYRAZOLE-4-CARBONITRILE is used as an insecticidal agent, leveraging its potential to control and manage insect populations, thereby serving as a component in the development of new pesticides.
Used in Anti-Fungal Applications:
1-Benzyl-1H-pyrazole-4-carbonitrile is utilized for its anti-fungal properties, being investigated for its ability to combat fungal infections and contribute to the creation of new anti-fungal treatments.
Each of these applications underscores the versatility and potential impact of 1-benzyl-1H-pyrazole-4-carbonitrile in advancing various fields of scientific and medical research.

InChI:InChI=1/C11H9N3/c12-6-11-7-13-14(9-11)8-10-4-2-1-3-5-10/h1-5,7,9H,8H2

Upstream product

• 63874-95-3 1-benzyl-1H-pyrazole-4carboxaldehyde 
• 121358-84-7 1-benzylpyrazole-4-carbaldoxime 
• 50877-41-3 1-benzyl-4-bromo-1H-pyrazole 
• 143-33-9 sodium cyanide 
• 100-44-7 benzyl chloride 
• 10199-67-4 1-benzylpyrazole 
• 544-92-3 copper(I) cyanide 
• 91091-13-3 5-amino-1-benzyl-1H-pyrazole-4-carbonitrile 
• 20570-96-1 benzylhydrazine dihydrochloride 
• 557-21-1 zinc(II) cyanide 
• 75-05-8 acetonitrile 
• 86164-70-7 2-methyl-2-phenylmalononitrile 
• 100-39-0 benzyl bromide 
• 14906-59-3 4-cyanopyridine N-oxide 

Downstream Products

• 936940-11-3 (1-benzyl-1H-pyrazol-4-yl)methanamine 
• 401647-24-3 1-benzyl-1H-pyrazole-4-carboxylic acid 

Relevant academic research and scientific papers

Copper-catalyzed domino halide exchange-cyanation of aryl bromides

An efficient copper-catalyzed domino halogen exchange-cyanation procedure for aryl bromides was developed utilizing 10 mol % CuI, 20 mol % KI, 1.0 equiv of the inexpensive N,N′-dimethylethylenediamine as ligand, and 1.2 equiv of NaCN in toluene at 110 °C. The new method represents a significant improvement over the traditional Rosenmund-von Braun reaction: the reaction conditions are much milder, and the use of stoichiometric amounts of copper(I) cyanide and polar solvents is avoided; therefore the isolation and purification of the aromatic nitrile products is greatly simplified. In addition, the new method exhibits excellent functional group compatibility comparable to that of the analogous Pd-catalyzed cyanation methodology. Copyright

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile: Via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine

We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP). Si-Me4-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C-CN bond cleavage.

N-alkyl-cyanopyrazole synthetic method

The invention discloses an N-alkyl-cyanopyrazole synthetic method which comprises the following step of by taking 1-alkyl-1H-pyrazole formaldehyde or a derivative thereof, ammonia water, sodium bromate and acetic acid as raw materials and water as a reaction solvent to obtain N-alkyl-cyanopyrazole . The synthetic method provided by the invention is simple in technology without using extremely toxic substances, convenient in synthesis, high in yield, convenient in purification of an obtained product and beneficial to large-scale industrial production.

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media

A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2-5 mol % catalyst loadings with temperatures ranging from rt to 40 °C. This mild method was applied to the synthesis of lersivirine, a reverse transcriptase inhibitor.

New application of heterocyclic diazonium salts. Synthesis of pyrazolo[3,4-d][1,2,3]triazin-4-ones and imidazo[4,5-d][1,2,3]triazin-4-ones

The pyrazolo[3,4-d][1,2,3]triazin-4-ones 3 and imidazo[4,5-d][1,2,3] triazin-4-ones 4 are analogs structurally related to purines that have showed a wide and significant variety of biological activity. These compounds were synthesized by one-pot diazotization of 5-amino-1H-pyrazole-4-carbonitriles 1 and 5-amino-1H-imidazole-4-carbonitriles 2, respectively.

New application of heterocyclic diazonium salts: Synthesis of new pyrazolo[3,4-d][1,2,3]triazin-4-ones

7-Substituted 3,7-dihydro-4H-pyrazolo[3,4-d][1,2,3]triazin-4-ones 2a-d were conveniently prepared by direct diazotization of 5-aminopyrazole-4- carbonitriles 1a-d in HCl media. Different reaction conditions and the effects of substituents on N-1 of the pyrazole ring were studied. A possible mechanistic exlpanation of the observed process is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

ARYL SULFONAMIDES

The present invention relates to compounds that modulate various chemokine receptors. These compounds are useful for treating inflammatory and immune diseases.

COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS

One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.