52807-17-7

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-methoxyphenyl)-3-methylpiperazine(SALTDATA: 2HCl 1.8H2O) is used as an intermediate in the synthesis of pharmaceutical products for its ability to contribute to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of various compounds with potential medicinal applications.
Used in Organic Chemistry:
In the field of organic chemistry, 1-(2-methoxyphenyl)-3-methylpiperazine(SALTDATA: 2HCl 1.8H2O) is used as a substrate for the production of other organic compounds. Its versatile structure enables it to be a valuable building block in the synthesis of a wide range of chemical products, including those with potential applications in various industries such as agriculture, materials science, and environmental science.
Used in Drug Development:
1-(2-methoxyphenyl)-3-methylpiperazine(SALTDATA: 2HCl 1.8H2O) is used as a starting material in drug development for its potential to be modified and incorporated into new therapeutic agents. Its piperazine derivative nature allows for the exploration of various chemical modifications, which can lead to the discovery of novel drugs with improved efficacy and safety profiles.

Upstream product

• 109613-00-5 4-acetophenyl triflate 
• 86487-17-4 2-tri-n-butylstannylanisole 
• 13329-40-3 4-Iodoacetophenone 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 99-90-1 para-bromoacetophenone 
• 100-66-3 methoxybenzene 
• 99-91-2 para-chloroacetophenone 
• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 
• 578-57-4 2-bromoanisole 
• 83724-41-8 tris(2-methoxyphenyl)bismuthine 
• 64101-67-3 4-acetylphenyl p-toluenesulfonate 
• 59099-58-0 2-methoxyphenyl triflate 
• 69497-83-2 4-acetylphenyl mesylate 
• 149104-90-5 4-acetylphenylboronic acid 

Relevant academic research and scientific papers

An efficient and reusable palladium catalyst supported on a rasta resin for Suzuki-Miyaura cross-couplings

A short and efficient synthesis of a heterogeneous palladium catalyst supported on a rasta resin bearing diphenylphosphanyl ligands is reported. This catalyst was used successfully for Suzuki-Miyaura reactions of aryl bromides in the presence of only 0.25 milli-equiv. of supported palladium. The catalyst was reused several times with no loss of efficiency, and the amount of palladium leached in the reaction medium is extremely low ( 1 % of the initial amount). An efficient heterogeneous palladium catalyst supported on a rasta resin bearing diphenylphosphanyl groups is reported. The catalyst was successfully used for Suzuki-Miyaura reactions of aryl bromides in the presence of only 0.25 milli-equiv. of supported palladium, it can be used at least five times, and the palladium leaching is very low ( 1 % of the initial amount). Copyright

Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction

A novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe3O4@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy?(TEM), Energy Dispersive X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES)?analysis was used to determine the exact amount of Pd (0.33?wt%) in Fe3O4@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst's structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki–Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a K2CO3 at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products in excellent yields with spectacular TOFs values (up to 1,960,339?h?1); in the presence of 1?mg of Fe3O4@SBA-15@NHC-Pd catalyst (contains 3.1 × 10–6?mol% Pd) at room temperature in aqueous media. After reusability experiments, it is found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. Graphic Abstract: [Figure not available: see fulltext.]

Pd–NPs@MMT–K10 Catalysis of Suzuki–Miyaura Cross-coupling Reaction: In Situ Generation and Ex Situ Use

Due to high surface area and low swelling property, Montmorillonite–K10 (MMT–K10) has been gaining widespread applications in heterogeneous catalysis as a material that is used for supporting varieties of catalyst species. The current report describes in situ generation of Pd–NPs@MMT–K10 catalytic system for heterogeneous catalysis of Suzuki–Miyaura (SM) cross-coupling reaction and it’s ex situ applications. While the in situ derived Pd@MMT–K10 was found very effective to deliver the coupling products within short span of time, the same when isolated and purified could serve equally as an externally added heterogeneous catalyst for the same reaction. In our observation, this report is first to include studies on ex situ application of in situ derived heterogeneous catalytic system by carrying out multiple new reactions with varied substrate combinations. PXRD, TEM and XPES studies were performed to have insight into the isolated catalytic system, while 1H & 13C NMR spectroscopy were used to establish the structure of the organic products. In terms of reusability, the catalytic system was very consistent in delivering SM cross-coupling product of 1-bromo-4-methoxybenzene & phenylboronic acid up to 5th run. Graphical Abstract: [Figure not available: see fulltext.]

Magnetite@MCM-41 nanoparticles as support material for Pd-N-heterocyclic carbene complex: A magnetically separable catalyst for Suzuki–Miyaura reaction

The Magnetite@MCM-41@NHC@Pd catalyst was obtained with Pd metal bound to the NHC ligand anchored to the surface of Fe3O4@MCM-41. It was characterized by Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy disperse X-ray analysis (EDX), thermogravimetric analysis (TGA), differential thermal analysis (DTA), and scanning electron microscopy (SEM). The amount of Pd in the Magnetite@MCM-41@NHC@Pd was measure by inductively coupled plasma–optical emission spectroscopy (ICP-OES) analysis. The catalytic activity of Magnetite@MCM-41@NHC@Pd heterogeneous catalyst done on Suzuki–Miyaura reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions afforded excellent yields and up to 408404 Turnover Frequency (TOF) h?1 in the presence of 2 mg of Magnetite@MCM-41@NHC@Pd catalyst (0.0564 mmol g?1, 0.01127 mmol% Pd) at room temperature in 2-propanol/H2O (1:2). Moreover, Magnetite@MCM-41@NHC@Pd catalyst was recover by applying the magnet and reused for another reaction. The catalyst showed excellent structural and chemical stability and reused ten times without a substantial loss in its catalytic performance.

N-heterocyclic carbene Pd(II) complex supported on Fe3O4@SiO2: Highly active, reusable and magnetically separable catalyst for Suzuki-Miyaura cross-coupling reactions in aqueous media

A new type magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was fabricated and characterized by Fourier Transform Infrared (FTIR) spectroscopy, Transmission Electron Microscopy (TEM), X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Energy Disperse X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA), and Scanning Electron Microscopy (SEM). The loading amount of Palladium (Pd) to magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs was measured by Inductively Coupled Plasma-Optical Emission Spectroscopy (ICP-OES) analysis. The catalytic activity of magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was examined on Suzuki-Miyaura cross-coupling reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions yielded excellent results and high TOF (up to 76528 h?1) in the presence of 2 mg of Fe3O4@SiO2@NHC@Pd-MNPs catalyst (0.0197 mmolg?1, 0.00394 mmol%Pd) at 80 °C in 2-propanol/H2O (1:2). In addition, the magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs catalyst was easily recovered by using an external Nd-magnet and reused for the Suzuki cross-coupling reactions. The catalyst showed strong structural and chemical stability and was reused six times without losing its catalytic activity substantially.

Palladium nanoparticle supported on nitrogen-doped porous carbon: Investigation of structural properties and catalytic activity on Suzuki–Miyaura reactions

Novel palladium-doped nanoporous carbon composite material obtained via thermolysis of amorphous zeolitic imidazolate framework (aZIF) was synthesized and used as an efficient catalyst on Suzuki–Miyaura cross-coupling reactions of aryl bromides. With this developed catalytic system, the Suzuki–Miyaura cross-coupling reaction was accomplished in aqueous solutions, and biaryls were obtained in good to excellent yields in a short reaction time. The APC-750@Pd catalyst was characterized by Fourier Transform Infrared spectroscopy (FTIR), X-ray Diffraction (XRD), Scanning Electron Eicroscopy (SEM), X-ray Photoelectron Spectroscopy (XPS), Transmission Electron Microscopy (TEM), Thermal Gravimetric Analysis (TGA), Differential Thermal Analysis (DTA), Inductively Coupled Plasma Mass Spectrometry (ICP-MS) and Brunauer–Emmett–Teller (BET) analysis tecniques. N-doped porous carbon material (NPC-1000) was synthesized by thermolysis from aZIF. Activated porous carbon material (APC-750) was fabricated via fused at 750°C with KOH from NPC-1000. The APC-750@Pd was obtained as a result of the interaction of APC-750 and PdCl2 in deionized water. The cross-coupling reaction of different aryl bromides with phenylboronic acid was investigated to show the potential of the APC-750@Pd in the Suzuki–Miyaura cross-coupling reactions. The APC-750@Pd catalyst could be recycled at least five times with a 15% loss of catalytic efficiency in this catalytic system.

Design of Benzimidazolyl Phosphines Bearing AlterableP,OorP,N-Coordination: Synthesis, Characterization, and Insights into Their Reactivity

A new series of hemilabile benzimidazolyl phosphines is reported. Entities in this ligand family can be easily assembled and prepared on a large scale via a simple one-pot procedure. X-ray crystallographic analyses show that the Pd metal center can coordinate in different fashions, where it relies on the size of the ?PR2group. With the same ligand scaffold, the ligand having a ?PCy2moiety displays better efficiency in expediting aromatic C-C bond-coupling reactions, while the ligand associated with a ?P-t-Bu2group, in contrast, promotes C-N bond-forming reactions.

Dual Nickel-/Palladium-Catalyzed Reductive Cross-Coupling Reactions between Two Phenol Derivatives

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance of phenols. Here, we report a dual nickel-/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2′-disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allows for straightforward late-stage functionalization, illustrated with examples such as ezetimibe and tyrosine.

A catalytic system with high efficiency and recyclability based on Suzuki and Heck reaction in aqueous admicellar medium

A recyclable and non-phosphine solid palladium (II) catalyst was prepared and characterized by HR-MS, FT-IR, XPS, EDS, TGA, SEM, TEM and ICP. The Pd-catalyst exhibited high-performance catalytic activity in Suzuki and Heck C-C coupling reactions in an environmentally benign water medium. Further, the Pd-catalyst (Z4) can be reused for 15 times with little decrease of activity through simple and efficient recovery. In addition, the turn-over number (TON) of Pd- catalyst can reach 380 at room temperature. These results proved that the Pd-catalyst has a stable structure and can be recycled many times, making the process sustainable.

Single monodentate N-donor ligands versus multi-ligand analogues in Pd(II)-catalysed C–C coupling at reduced temperatures

Deployment of reduced operational temperatures is industrially beneficial and use of the highly efficient, phosphine-based precatalysts is limited by their high costs and inaccessible preparation procedures. In order to study of the influence of coordination environments on catalyst reactivities at reduced temperatures, design of palladium(II) complexes bearing single monodentate N-donor ligands was considered necessary. Consequently, dichloridopalladium(II) complexes of 2-(thiophen-2-yl)-1H-imidazole ligands (1–8), 2,4,5-triphenyloxazole (9) and 2-(1H-imidazol-2-yl)pyridine (10) have been prepared, structurally characterized and studied as N-stabilized precatalysts. Ligand donor strengths were spectroscopically estimated by protonation-deprotonation equilibria. The palladium(II) complexes were obtained in three coordination environments; (i) the mono-ligand complexes bearing trans-solvent co-ligands (PdL.acn and PdL.dmf), (ii) the chlorido-bridged dimers μ-(PdL)2 and (iii) the trans-bis-ligand PdL2 complexes. Considering ambient temperature operations, the catalysis outcomes obtained for the monodentate mono-ligand coordination designs represent an improvement in terms of temperature and reaction time relative to previously reported N-stabilized palladium precatalysts. The mono-ligand pre-catalysts efficiently generate living active palladium species from 40 °C while a trans-bis-ligand phosphine-based pre-catalyst analogue PdI2(PPh3)2 displayed no yield under the same temperature conditions. Trans-bis-ligand coordination is observed to utterly hinders catalyst efficiencies at the studied temperatures and preformed mono-ligand complexes of mono-dentate N-donors provided positive ligand effects while in situ catalyst generation failed. Therefore, the use of multiple ligand equivalents should be discouraged.