57211-65-1

Usage

Chemical structure

A pyrazole derivative containing a chlorophenyl group

Potential applications

Building block for pharmaceuticals and agrochemicals, research and development in medicinal chemistry and crop protection, other industrial processes and products

Unique properties

Versatile chemical with specific reactivity and properties that make it useful in a wide range of applications

Upstream product

• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 288-13-1 NH-pyrazole 
• 625-99-0 3-iodochlorobenzene 
• 63503-60-6 3-chlorophenylboronic acid 
• 52827-07-3 3-(3-chlorophenyl)sydnone 
• 79-10-7 acrylic acid 
• 108-42-9 3-chloro-aniline 
• 541-73-1 1,3-Dichlorobenzene 
• 1404120-23-5 (4-chloro-2-(1H-pyrazol-1-yl)phenyl)(phenyl)methanol 
• 625-98-9 3-chlorofluorobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 14763-20-3 3-chlorophenyl hydrazine 

Downstream Products

• 400877-26-1 1-(3-chlorophenyl)-1H-pyrazole-4-carbaldehyde 
• 1260140-74-6 8-chloro-4,5-diphenylpyrazolo[1,5-a]quinoline 
• 907210-12-2 N-[3-(1-pyrazolyl)phenyl]aniline 

Relevant academic research and scientific papers

Complexes of Rhodium(III) with Two Chelating CN Ligands and One Diimine Ligand

The synthesis of two series of cyclometalated RhIII compounds is described, namely of 5 dinuclear chloro-bridged species N)2>(μ-Cl)2> A and of 15 mononuclear complexes N)2(NN)>+ B; CN stands for five different cyclometalating ligands, i.e. deprotonated phenylpyridine, deprotonated 2-(thienyl)pyridine, and three deprotonated 1-aryl-1H-pyrazoles, and NN for six diimine ligands such as 2,2'-bipyridine, 2,2'-bi-1H-imidazole, and 2,2'-bipyrimidine.For (2,2'-bipyridine)bis3'>rhodium(III) chloride, an X-ray structure determination was carried out.In the other cases, 1H-NMR spectra established the configuration of the complexes.All mononuclear and dinuclear complexes show a C,C cis-configuration.The UV/VIS-absorption bands at longest wavelength are most likely due to metal-to-ligand charge-transfer (MLCT) transitions, depending on the nature of the cyclometalating ligand CN and on the diimine ligand NN.The receptor orbital is in some cases on the cyclometalating ligand, in others on the diimine.All monomer complexes exhibit at least one reversible reduction wave in the cyclovoltammogram in dimethylformamide solutions, attributable to a ligand-centered reduction.It is, therefore, concluded that the LUMO in N)2(NN)>+ is of L(?*)character, as opposed to 3+, where it is a metal d-orbital.The crystal system of (2,2'-bipyridine)bis3'>rhodium(III) chloride-water(1/2.125) is tetragonal (space group P4; R=0.036, Rw=0.040).The Rh-atom has slightly distorted octahedral environment; the average distances are Rh-N/thienyl-pyridine)=2.060 (3), Rh-C=1.9885 (3), and Rh-N(bipyridine)=2.1415 (3) Angstroem.Of the three ligands the 2,2'-bipyridine is the most planar.

α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles

The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.

A N - aryl pyrazole compounds and N - aryl imidazole compound of preparation method

The invention discloses a preparation method of an N-arylpyrazole compound and an N-arylimidazole compound. The method comprises the following steps: reacting at 20-120 DEG C for 6-48 hours by taking aryl halide and pyrazole or imidazole as substrates and copper salt as a catalyst in an organic solvent in the presence of alkali and a nitrogenous ligand under nitrogen protection; and after the reaction is finished, separating and purifying a reaction liquid to obtain the N-arylpyrazole compound or the N-arylimidazole compound. A product prepared by utilizing the method disclosed by the invention can not only be directly used, but also be used for other reactions as a substrate and has the advantages of moderation in adopted reaction condition, simple operation step and post-processing process, high yield and suitability for large-scale production.

Facile Synthesis of 1-Arylpyrazoles

A convenient and transition-metal-free synthesis of 1-arylpyrazoles that involves the cycloaddition of 3-arylsydnones and acrylic acid is presented. The process proceeds smoothly to obtain the target products with moderate to high yields.

Copper-catalyzed arylation of nitrogen heterocycles from anilines under ligand-free conditions

The arylation of pyrazole and derivatives can be achieved by coupling arenediazonium species (formed in situ from anilines) by using a catalytic system that employs low-toxicity and inexpensive copper metal under very mild and ligand-free conditions (T = 20 ° C). From other nitrogen heterocycles, the presence of an additive (NBu4I) significantly improves the efficiency of the catalytic system. These results represent the first examples of C-N bond formation from arenediazonium species.

Direct N-arylation of azaheterocycles with aryl halides under ligand-free condition

A simple and efficient Ci￡N cross-coupling method of aryl halides with various heterocycles was reported, by using 10 mol% of CuI as catalyst and 1.2 equiv. NaH as base. Aryl iodides, aryl bromides and many substituted aryl chlorides could efficiently react with heterocycles, providing variety of N-arylated products in good to excellent yields. The ligand-free catalyst system was stable in air and could be readily reused. An efficient, convenient and applicable method was developed for the N-arylation of azaheterocycles catalyzed by CuI and NaH under ligand free condition. Copyright

Reductive cleavage of the Csp2-Csp3 bond of secondary benzyl alcohols: Rhodium catalysis directed by N-containing groups

Cutting loose: 1,1-Biarylmethanol substrates undergo reductive cleavage of the C-C bond in the presence of a cationic RhIII catalyst and H 2 (see scheme; DG=directing group). Various functional groups are tolerated in the reaction system. Preliminary studies indicate that a five-membered rhodacycle intermediate, which then converts into a Rh III hydride species for the reduction, is involved in the catalytic cycle. Copyright

Catalyst-free N-arylation using unactivated fluorobenzenes

Caught in a 'SNAr'e: A one-step, high-yielding, catalyst-free method is described for N-arylation of azoles and indoles from unactivated monofluorobenzenes. This SNAr reaction tolerates a wide range of substituents and can also generate halogenated N-aryl products. The reaction can also be performed simultaneously with or subsequent to a copper- or palladium-catalyzed cross-coupling reaction in the same pot. Copyright

A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water

An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to 94%) under the described arylation conditions.

Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst

Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.