80565-30-6

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-CHLOROPHENYL)BENZALDEHYDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-(2-CHLOROPHENYL)BENZALDEHYDE is utilized as a building block for the synthesis of complex organic molecules. Its reactivity and functional groups make it suitable for a wide range of chemical reactions.
Used in Antimicrobial Agents:
4-(2-CHLOROPHENYL)BENZALDEHYDE is used in the synthesis of thieno[3,2-d]pyrimidines, which serve as scaffolds for antimicrobial activity. These compounds have potential applications in the development of new antimicrobial drugs to combat resistant bacterial strains.
Used in Research and Development:
Due to its unique structure and reactivity, 4-(2-CHLOROPHENYL)BENZALDEHYDE is also used in research and development settings to explore new chemical reactions and investigate its potential applications in various fields, including materials science and medicinal chemistry.

Upstream product

• 106-39-8 bromochlorobenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 21700-74-3 (p-chlorophenyl)triethoxysilane 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 64-18-6 formic acid 
• 2051-62-9 4'-biphenyl chloride 
• 87199-17-5 4-formylphenylboronic acid, 
• 29304-86-7 7-(4-chlorophenyl)-cyclohepta-1,3,5-triene 
• 106-48-9 4-chloro-phenol 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 1679-18-1 4-Chlorophenylboronic acid 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 75-52-5 nitromethane 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 98629-82-4 5,5'-<4'-chloro-1,1'-biphenyl>-4-ylmethylenebis(6-methylaminouracil) 
• 15996-82-4 (4'-chloro-[1,1'-biphenyl]-4-yl)methanamine 
• 5748-41-4 4'-chlorobiphenyl-4-carboxylic acid 
• 22494-48-0 (4′-chloro-[1,1′-biphenyl]-4-yl)methanol 
• 516481-36-0 2-[4-(4-Chloro-phenyl)-phenyl]-1H-benzoimidazole-5-carboxylic Acid 
• 80565-31-7 2-[4-(4-chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-one 
• 80565-32-8 2-[4-(4-chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one 

Relevant academic research and scientific papers

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

KDS2010, a Newly Developed Reversible MAO-B Inhibitor, as an Effective Therapeutic Candidate for Parkinson’s Disease

Monoamine oxidase-B (MAO-B) is a well-established therapeutic target for Parkinson’s disease (PD); however, previous clinical studies on currently available irreversible MAO-B inhibitors have yielded disappointing neuroprotective effects. Here, we tested the therapeutic potential of KDS2010, a recently synthesized potent, selective, and reversible MAO-B inhibitor in multiple animal models of PD. We designed and synthesized a series of α-aminoamide derivatives and found that derivative KDS2010 exhibited the highest potency, specificity, reversibility, and bioavailability (> 100%). In addition, KDS2010 demonstrated significant neuroprotective and anti-neuroinflammatory efficacy against nigrostriatal pathway destruction in the mouse MPTP model of parkinsonism. Treatment with KDS2010 also alleviated parkinsonian motor dysfunction in 6-hydroxydopamine-induced and A53T mutant α-synuclein overexpression rat models of PD. Moreover, KDS2010 showed virtually no toxicity or side effects in non-human primates. KDS2010 could be a next-generation therapeutic candidate for PD.

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

Solvent Effects on the Selectivity of Palladium-Catalyzed Suzuki-Miyaura Couplings

The use of polar solvents MeCN or dimethylformamide (DMF) was previously shown to induce a selectivity switch in the Pd/PtBu3-catalyzed Suzuki-Miyaura coupling of chloroaryl triflates. This phenomenon was attributed to the ability of polar solvents to stabilize anionic transition states for oxidative addition. However, we demonstrate that selectivity in this reaction does not trend with solvent dielectic constant. Unlike MeCN and DMF, water, alcohols, and several polar aprotic solvents such as MeNO2, acetone, and propylene carbonate provide the same selectivity as nonpolar solvents. These results indicate that the role of solvent on the selectivity of Suzuki-Miyaura couplings may be more complex than previously envisioned. Furthermore, this observation has the potential for synthetic value as it greatly broadens the scope of solvents that can be used for chloride-selective cross coupling of chloroaryl triflates.

(N-Heterocyclic carbene) ion-pair palladium complexes: Suzuki–Miyaura cross-coupling studies in neat water under mild conditions

The synthesis and characterization of a series of (N-heterocyclic carbene)PdCl3?(NMe3H)+ ion-pair complexes are presented. Applying the quaternary ammonium salt as the function with NHC–Pd(II) complexes yields the new ion-pair complexes. The NHC–Pd(II) ion-pair complexes work well by undergoing the Suzuki–Miyaura reaction with aryl chloride substrates in water under mild conditions in air at room temperature. Twenty products resulting from Suzuki–Miyaura coupling reactions carried out in the presence of the new NHC–Pd(II) ion-pair complex under mild optimal conditions were examined to determine the optimum yields.

Salicylaldehyde-stabilized palladium nanoparticles for highly efficient suzuki-miyaura reaction at room temperature

Pd-catalyzed Suzuki-Miyaura cross-coupling reactions promoted by simple and commercial salicylaldehyde-based ligands were investigated. The effect of the ligands was evaluated and the reaction conditions were optimized. Moreover, the physical nature of the palladium was determined by TEM analysis and poison tests. It demonstrated that this catalytic system can be reused for ten consecutive runs and showed excellent activities toward aryl bromides with arylboronic acids at room temperature in air.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling

Two N-heterocyclic carbene ligands provide orthogonal chemoselectivity during the Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling of chloroaryl triflates. The use of SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene] leads to selective cross-coupling at chloride, while the use of SIMes [SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] provides selective coupling at triflate. With most chloroaryl triflates and arylboronic acids, ligand-controlled selectivity is high (≥10:1). The scope of this methodology is significantly more general than previously reported methods for selective SM coupling of chloroaryl triflates using phosphine ligands. Density functional theory studies suggest that palladium's ligation state during oxidative addition is different with SIMes compared to SIPr.

PdII Immobilized on Ferromagnetic Multi-Walled Carbon Nanotubes Functionalized by Aminated 2-Chloroethylphosphonic Acid with S -Methylisothiourea (FMMWCNTs@CPA@SMTU@PdII NPs) Applied as a Highly Efficient and Recyclable Nanostructured Catalyst for Suzuki-Miyaura and Mizoroki-Heck Cross-Coupling Reactions in Solvent-Free Conditions

The new ferromagnetic nanostructured FMMWCNTs@CPA@SMTU@PdII NPs (IV) as an eco-friendly heterogeneous nanocatalyst with a particle size of ～20-30 nm reported earlier by our group has been found to be very effective for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions at ambient temperature. The procedure has been applied for a wide range of aryl halides, arylboronic acids, and alkenes. The magnetic separation by an external magnetic field, mild reaction conditions, and catalyst reusability up to four times without significant decrease in catalytic activity (reduced catalytic activity from 11 to 18 % in the fifth, sixth, and seventh cycles) made the present method sustainable and economically viable for C-C cross-coupling reactions.

Synthesis and characterization of Pd-γ-Fe2O3 nanocomposite and its application as a magnetically recyclable catalyst in ligand-free Suzuki-Miyaura reaction in water

A novel redox-driven method to synthesize Pd-γ-Fe2O3 nanocomposite from Fe3O4 and PdCl2 under modified hydrothermal technique has been developed. The synthesized nanocomposite was characterized by XRD, FT-IR, XPS, FESEM, TEM and EDX to understand the composition as well as morphology. The Pd-γ-Fe2O3 nanocomposite was found to show excellent catalytic activity towards Suzuki-Miyaura cross-coupling reactions in water without the assistance of ligands, organic solvents or phase transfer catalysts. A wide range of functional substitutions in aryl halide as well as arylboronic acid moieties is tolerated in the developed protocol. The nanocatalyst can be recovered magnetically, and reused up to six cycles without significant loss in its catalytic activity.