67455-41-8

Usage

Uses

Used in Agrochemical Industry:
4-PIPERAZIN-1-YL-PHENYLAMINE is used as a key intermediate for the synthesis of various agrochemicals, specifically pesticides and herbicides. Its unique chemical structure allows for the development of compounds that can effectively target and control pests and weeds, contributing to increased crop yields and protection against damage.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-PIPERAZIN-1-YL-PHENYLAMINE serves as a crucial building block for the development of new drugs, particularly those targeting the central nervous system. Its structural properties enable the creation of molecules with potential applications in the treatment of various neurological and psychiatric disorders, such as anxiety, depression, and schizophrenia.
Used in Dyestuff Industry:
4-PIPERAZIN-1-YL-PHENYLAMINE is also utilized in the dyestuff industry as a starting material for the production of various types of dyes. Its chemical versatility allows for the synthesis of a wide range of colors and shades, making it a valuable component in the formulation of dyes for textiles, plastics, and other materials.

InChI:InChI=1/C10H15N3/c11-9-1-3-10(4-2-9)13-7-5-12-6-8-13/h1-4,12H,5-8,11H2

Upstream product

• 100-25-4 para-dinitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 170911-92-9 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine 
• 371-40-4 4-fluoroaniline 
• 100-01-6 4-nitro-aniline 
• 43204-63-3 bis(2-bromoethyl)amine hydrobromide 
• 100-00-5 4-chlorobenzonitrile 
• 586-78-7 para-nitrophenyl bromide 
• 6269-89-2 1-(4-Nitrophenyl)piperazine 

Downstream Products

• 153466-15-0 4-[4-(4-nitro-phenyl)-piperazin-1-yl]-phenylamine 
• 399011-43-9 methyl {3-[4-(4-aminophenyl)piperazin-1-yl]}-propionate 
• 92394-00-8 1-acetyl-4-(4-aminophenyl)piperazine 
• 748777-37-9 N-(4-piperazin-1-yl-phenyl)-3-[2-(4-piperazin-1-yl-phenylcarbamoyl)-ethyldisulfanyl]-propionamide 
• 74853-08-0 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine 
• 112559-81-6 N-(4-Hydroxyphenyl)-N'-(4'-nitrophenyl)-piperazine 
• 1099656-99-1 C₂₇H₃₂Cl₂N₈O 
• 955369-29-6 3-[4-(4-aminophenyl)piperazin-1-yl]propionitrile 
• 1197170-01-6 C₃₁H₃₉N₉O₃ 
• 1197169-96-2 C₃₁H₃₈N₈O₃ 
• 1144073-54-0 1-{4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}-3-(4-piperazin-1-ylphenyl)urea 
• 947673-12-3 benzyl 4-(4-aminophenyl)piperazine-1-carboxylate 
• 1291141-89-3 3-[4-(4-aminophenyl)piperazin-1-yl]-1-benzo[b]thiophen-3-yl-propan-1-one 
• 1353642-58-6 4-methyl-N-(4-(piperazin-1-yl)phenyl)aniline 

Relevant academic research and scientific papers

Rhodium-terpyridine Catalyzed Transfer Hydrogenation of Aromatic Nitro Compounds in Water

A rhodium terpyridine complex catalyzed transfer hydrogenation of nitroarenes to anilines with i-PrOH as hydrogen source and water as solvent has been developed. The catalytic system can work at a substrate/catalyst (S/C) ratio of 2000, with a turnover frequency (TOF) up to 3360 h?1, which represents one of the most active catalytic transfer hydrogenation systems for nitroarene reduction. The catalytic system is operationally simple and the protocol could be scaled up to 20 gram scale. The water-soluble catalyst bearing a carboxyl group could be recycled 15 times without significant loss of activity.

Methylene violet derivative fluorescent probe as well as synthesis method and application thereof

The invention discloses a methylene violet derivative fluorescent probe as well as a synthesis method and application thereof. The fluorescent probe is connected with an NBD group through piperazine on the basis of a cationic main structure of methylene violet. The preparation method comprises the following steps: directly reacting methylene violet 3RAX with piperazine, or firstly reacting with X-R5-X and then reacting with piperazine, and finally introducing an NBD group to a piperazine group to obtain the target fluorescent probe; or reacting 4-fluoronitrobenzene, piperazine and aniline to obtain a cationic main structure of methylene violet, and finally introducing an NBD group to a piperazine group to obtain the target fluorescent probe. The fluorescent probe is good in water solubility, can be used for sulfur ion detection, is high in detection sensitivity and low in detection limit, and can also be used as a tumor photodynamic therapy probe to quickly release singlet oxygen for tumor photodynamic therapy; synthesis is simple, conditions are mild, and cost is low.

Method for reducing aromatic nitro compounds into aromatic amine compounds

The invention discloses a method for reducing aromatic nitro compounds into aromatic amine compounds. The aromatic nitro compounds are reacted at a temperature of 110-130 DEG C in an inert or air atmosphere under the action of a rhodium catalyst by using water as a solvent, isopropanol as a hydrogen source and potassium phosphate or sodium carbonate as an alkali to obtain the aromatic amine compounds. The method has the advantages of simplicity in operation, greenness, environmental friendliness, reduction of environmental pollution, high reaction yield, amplified gram-scale preparation of theamine compounds, high catalyst activity, recyclability and low industrial production cost.

Discovery and SARs of 5-Chloro- N4-phenyl- N2-(pyridin-2-yl)pyrimidine-2,4-diamine Derivatives as Oral Available and Dual CDK 6 and 9 Inhibitors with Potent Antitumor Activity

Cyclin-dependent kinases (CDKs) are promising therapeutic targets for cancer therapy. Herein, we describe our efforts toward the discovery of a series of 5-chloro-N4-phenyl-N2-(pyridin-2-yl)pyrimidine-2,4-diamine derivatives as dual CDK6 and 9 inhibitors. Intensive structural modifications lead to the identification of compound 66 as the most active dual CDK6/9 inhibitor with balancing potency against these two targets and good selectivity over CDK2. Further biological studies revealed that compound 66 was directly bound to CDK6/9, resulting in suppression of their downstream signaling pathway and inhibition of cell proliferation by blocking cell cycle progression and inducing cellular apoptosis. More importantly, compound 66 significantly inhibited tumor growth in a xenograft mouse model with no obvious toxicity, indicating the promising therapeutic potential of CDK6/9 dual inhibitors for cancer treatment. Therefore, the above results are of great importance in the development of dual CDK6/9 inhibitors for cancer therapy.

Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst

A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.

Design, synthesis and biological evaluation of novel osthole-based derivatives as potential neuroprotective agents

A total of 26 compounds based on osthole skeleton were designed, synthesized. Their cytoprotective abilities of antioxidation, anti-inflammation and Aβ42(Amyloid β-protein 42)-induced neurotoxicity were evaluated by MTT assays. Mechanism of the action of selected compounds were investigated by molecular docking. AlogP, logS and blood–brain barrier (BBB) permeability of all these compounds were simulated by admetSAR. Most of the compounds showed better antioxidative and anti-inflammatory activities compared with osthole, especially OST7 and OST17. The compound OST7 showed relative high activity in neuroprotection against H2O2 (45.7 ± 5.5%), oxygen glucose deprivation (64.6 ± 4.8%) and Aβ42 (61.4 ± 5.2%) at a low concentration of 10 μM. EC50 of selected compounds were measured in both H2O2 and OGD induced cytotoxicity models. Moreover, NO inhibiting ability of OST17(50.4 ± 7.1%) already surpassed the positive drug indomethacin. The structure activity relationship study indicated that introduction of piperazine group, tetrahydropyrrole group and aromatic amine group might be beneficial for enhancement of osthole neuroprotective properties. Molecular docking explained that the reason OST7 exhibited relatively stronger neuroprotection against Aβ because of the greater area of interactions between molecule and target protein. OST7 and OST17 both provided novel methods to investigate osthole as anti-AD drugs.

Nitrogen-containing heterocycle derivatives and applications thereof

The invention discloses nitrogen-containing heterocycle derivatives and applications thereof, relates to compounds of a general formula (V), a preparing method thereof and applications of the compounds in medicines, and more particularly relates to compound derivatives of compounds shown as the general formula (V), a preparing method thereof and uses of the derivatives in medicines preventing andtreating hyperlipemia, hypercholesterolemia, hypertriglyceridemia, fatty degeneration of liver, diabetes mellitus type 2, hyperglycemia, obesity or insulin resistance and metabolic syndrome and resisting antitumor, with the derivatives being adopted as therapeutic agents. The compounds disclosed by the invention can also reduce total cholesterol, LDL-cholesterol and triglyceride, can increase liver LDL receptor expression, and inhibit PCSK9 expression.

Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts

The development of efficient and selective nanostructured catalysts for industrially relevant hydrogenation reactions continues to be an actual goal of chemical research. In particular, the hydrogenation of nitriles and nitroarenes is of importance for the production of primary amines, which constitute essential feedstocks and key intermediates for advanced chemicals, life science molecules and materials. Herein, we report the preparation of graphene shell encapsulated Co3O4- and Co-nanoparticles supported on carbon by the template synthesis of cobalt-terephthalic acid MOF on carbon and subsequent pyrolysis. The resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale and recycling of the catalyst.

Metallo-supramolecular polymer engineered porous carbon framework encapsulated stable ultra-small nanoparticles: A general approach to construct highly dispersed catalysts

The development of a general approach for fabricating stable ultra-small heterogeneous nanocatalysts has been intensively pursued. However, issues related to complex synthesis processes and structural stability have restricted their investigation and application. Here we report a facile organometallic conjunction strategy for the large-scale fabrication of porous carbon framework encapsulated highly dispersed sub-3 nm ultra-small nanoparticles (USMNPs@PCF). This methodology is based on the convenient aldol condensation reaction to manufacture a metallo-supramolecular polymer precursor and then consequent annealing to form the target nanocomposite. This technique was successfully applied to the preparation of varieties of USMNPs@PCF, including Fe, Co, Ni, Mo, Ru, Rh, Pd and Pt. As a representative application, the PCF encapsulated sub-3 nm Pd nanoparticles demonstrated remarkable durability and efficiency for chemoselective hydrogenation of nitroarenes to their corresponding anilines under ambient conditions with low catalyst loading. All hydrogenation reactions can complete in 4 min with >99% conversion and >99% chemoselectivity. The turnover frequency (TOF) was up to 11:400 h-1 for p-nitrophenol. This work provides a general, scalable and economical route for the manufacture of sub-3 nm and highly dispersed nanocomposites, which can be used in many other important fields, such as electrochemistry, energy science and environmental protection.

Porous silica-encapsulated and magnetically recoverable Rh NPs: A highly efficient, stable and green catalyst for catalytic transfer hydrogenation with "slow-release" of stoichiometric hydrazine in water

A core-shell structured nanocatalyst (Fe3O4@SiO2-NH2-RhNPs@mSiO2) that is encapsulated with porous silica has been designed and prepared for catalyzing the transfer hydrogenation of nitro compounds into corresponding amines. Rh nanoparticles serve as the activity center, and the porous silica shell plays an important role in the "slow-release" of the hydrogen source hydrazine. This reaction can be carried out smoothly in the green solvent water, and the atom economy can be improved by decreasing the amount of hydrazine hydrate used to a stoichiometric 1.5 equivalent of the substrate. Significantly, high catalytic efficiency is obtained and the turnover frequency (TOF) can be up to 4373 h-1 in the reduction of p-nitrophenol (4-NP). A kinetics study shows that the order of reaction is ～0.5 towards 4-NP, and the apparent active energy Ea is 58.18 kJ mol-1, which also gives evidence of the high catalytic efficiency. Additionally, the excellent stability of the catalyst has been verified after 15 cycles without any loss of catalytic activity, and it is easily recovered by a magnet after reaction due to the Fe3O4 nucleus.