50877-41-3

Usage

Uses

Used in Pharmaceutical and Chemical Synthesis:
1-Benzyl-4-bromo-1H-pyrazole is used as an intermediate in the synthesis of various amines and amino acids that contain the pyrazole nucleus. These compounds are of interest due to their close structural resemblance to imidazole derivatives, such as histamine and histidine, which are biologically active molecules with significant roles in physiological processes.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-Benzyl-4-bromo-1H-pyrazole is utilized as a building block for the development of new pharmaceutical agents. Its unique structure allows for the design of molecules with potential therapeutic applications, such as modulating specific biological targets or pathways.
Used in Research and Development:
1-Benzyl-4-bromo-1H-pyrazole is also used in research and development settings to explore its chemical properties and potential interactions with biological systems. This can lead to a better understanding of its role in chemical and biological processes, as well as the discovery of new applications in various industries.
Overall, 1-Benzyl-4-bromo-1H-pyrazole is a versatile compound with a range of applications in pharmaceuticals, chemical synthesis, and research, making it a valuable asset in the development of new technologies and therapeutic agents.

InChI:InChI=1/C10H9BrN2/c11-10-6-12-13(8-10)7-9-4-2-1-3-5-9/h1-6,8H,7H2

Upstream product

• 10199-67-4 1-benzylpyrazole 
• 2075-45-8 4-bromo-1H-pyrazole 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 121358-86-9 1-benzyl-1H-pyrazole-4-carbonitrile 
• 936940-11-3 (1-benzyl-1H-pyrazol-4-yl)methanamine 
• 401647-24-3 1-benzyl-1H-pyrazole-4-carboxylic acid 
• 1316228-69-9 3-(1-benzyl-1H-pyrazole-4-yl)-1H-pyrrolo[2,3-b]pyridine 
• 1393880-04-0 1-benzyl-4-(1-methyl-1H-imidazol-2-yl)-1H-pyrazole 
• 1393880-06-2 1-benzyl-4-(thiophen-2-yl)-1H-pyrazole 
• 1393879-89-4 1-benzyl-4-(furan-2-yl)-1H-pyrazole 
• 761446-45-1 1-(phenylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 700360-08-3 1-benzyl-4-phenyl-1H-1,2,3-triazole 

Relevant academic research and scientific papers

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.

Pyrazole N-alkylation method

The invention provides a pyrazole N-alkylation method. Pyrazole or pyrazole derivatives and alkyl halogenated hydrocarbons react in a solvent under the existence of quaternary ammonium salt catalysts;N-alkyl substituted pyrazole is obtained. The method provided by the invention has the advantages that the operation is simple; the cost is low; the anhydrous oxygen-free environment is not needed; heating is not needed; the yield is high; the amplified industrialized production can be easily realized.

A mild halogenation of pyrazoles using sodium halide salts and Oxone

A mild, inexpensive, and operationally simple pyrazole halogenation method utilizing Oxone and sodium halide salts is reported. This work documents 17 examples of alkyl, aryl, allyl, and benzyl substituted 4-chloro and 4-bromopyrazoles, obtained in up to 93% yield. Reactions are performed in water under ambient conditions and generation of organic byproducts is avoided.

N-ALKYLARYL-5-OXYARYL-OCTAHYDRO-CYCLOPENTA[C]PYRROLE NEGATIVE ALLOSTERIC MODULATORS OF NR2B

The present invention relates to N-alkylaryl-5-oxyaryl-octadihydrocyclopent[c]pyrrole negative allosteric modulators of NR2B receptors useful in the treatment of neurological diseases having the Formula I where R1, R2, L1, L2, X, Y, and Y' are described t

A versatile method for suzuki cross-coupling reactions of nitrogen heterocycles

(Chemical Equation Presented) A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme; dba = dibenzylideneacetone, Cy = cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2-and OH-substituted substrates), and efficient even with unactivated aryl chlorides.

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.

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

2-Substituted Pyrazole 1-Oxides. Preparation and Reaction with Electrophilic Reagents

1-Substituted pyrazoles have been oxidized by peracids to 2-substituted pyrazole 1-oxides.This leads to a change in reactivity towards electrophilic attack. 2-Benzylpyrazole 1-oxide is brominated, chlorinated, and nitrated selectively at C-3.The 3-halo-su