126485-58-3

Usage

Uses

Used in Chemical Synthesis:
3-(3-METHOXYPHENYL)BENZALDEHYDE is used as a reagent for the preparation of arylsilanes, which are important intermediates in various chemical reactions. The presence of the methoxy group on the biphenyl structure enhances the reactivity of the compound, making it a valuable component in the synthesis of arylsilanes.
Used in Cross-Coupling Reactions:
In the field of organic chemistry, 3-(3-METHOXYPHENYL)BENZALDEHYDE plays a crucial role in cross-coupling reactions. These reactions are widely used for the formation of carbon-carbon bonds, which are essential in the synthesis of complex organic molecules. The reactivity of 3-(3-METHOXYPHENYL)BENZALDEHYDE allows for efficient coupling with other organic compounds, facilitating the synthesis of a wide range of chemical products.
Used in Pharmaceutical Industry:
3-(3-METHOXYPHENYL)BENZALDEHYDE and its derivatives have potential applications in the pharmaceutical industry. The unique structure and reactivity of 3-(3-METHOXYPHENYL)BENZALDEHYDE make it a promising candidate for the development of new drugs and drug candidates. Its use in the synthesis of biologically active molecules can lead to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in Material Science:
In the field of material science, 3-(3-METHOXYPHENYL)BENZALDEHYDE can be utilized in the development of new materials with specific properties. Its reactivity and structural features can be exploited to create materials with tailored characteristics, such as improved conductivity, stability, or optical properties. This can lead to the development of innovative materials for various applications, including electronics, sensors, and energy storage devices.

InChI:InChI=1/C14H12O2/c1-16-14-7-3-6-13(9-14)12-5-2-4-11(8-12)10-15/h2-10H,1H3

Upstream product

• 10365-98-7 3-methoxyphenylboronic acid 
• 3132-99-8 m-bromobenzoic aldehyde 
• 591-20-8 3-Bromophenol 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 380151-86-0 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarboxaldehyde 
• 2398-37-0 3-methoxyphenyl bromide 
• 87199-16-4 3-Formylphenylboronic acid 
• 142344-35-2 Dichloro(3-methoxyphenyl)(propyl)silane 
• 57455-06-8 3-iodobenzylalcohol 
• 696-41-3 m-iodobenzaldehyde 
• 126485-53-8 (difluoro)(3-methoxyphenyl)(n-propyl)silane 

Downstream Products

• 773872-43-8 (3'-methoxybiphenyl-3-yl)methanol 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel dual FFA1 and PPARδ agonists possessing phenoxyacetic acid scaffold

The free fatty acid receptor 1 (FFA1/GPR40) and peroxisome proliferator-activated receptor δ (PPARδ) have been widely considered as promising targets for type 2 diabetes mellitus (T2DM) due to their respective roles in promoting insulin secretion and impr

2-thioxothiazolidin-4-one analogs as pan-pim kinase inhibitors

Proviral integration site for Moloney murine leukemia virus (PIM) kinases are proto-oncogenic kinases involved in the regulation of several cellular processes. PIM kinases are promising targets for new drug development because they play a major role in many cancer-specific pathways, such as survival, apoptosis, proliferation, cell cycle regulation, and migration. Here, 2-thioxothiazolidin-4-one derivatives were synthesized and evaluated as potent pan-PIM kinase inhibitors. Optimized compounds showed single-digit nanomolar IC50 values against all three PIM kinases with high selectivity over 14 other kinases. Compound 17 inhibited the growth of Molm-16 cell lines (EC50 = 14 nM) and modulated the expression of pBAD and p4EBP1 in a dose-dependent manner.

Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.

Dissection of complex molecular recognition interfaces

The synthesis of a family of zinc porphyrins and pyridine ligands equipped with peripheral H-bonding functionality has provided access to a wide range of closely related supramolecular complexes featuring between zero and four intramolecular H-bonds. An automated UV/vis titration system was used to characterize 120 different complexes, and these data were used to construct a large of number of different chemical double mutant cycles to quantify the intramolecular H-bonding interactions. The results probe the quantitative structure-activity relationship that governs cooperativity in the assembly of complex molecular recognition interfaces. Specifically, variations in the chemical structures of the complexes have allowed us to change the supramolecular architecture, conformational flexibility, geometric complementarity, the number and nature of the H-bond interactions, and the overall stability of the complex. The free energy contributions from individual H-bonds are additive, and there is remarkably little variation with architecture in the effective molarity for the formation of intramolecular interactions. Intramolecular H-bonds are not observed in complexes where they are geometrically impossible, but there are no cases where excellent geometric complementarity leads to very high affinities. Similarly, changes in conformational flexibility seem to have limited impact on the values of effective molarity (EM). The major variation that was found for all of the 48 intramolecular interactions that were examined using double mutant cycles is that the values of EM for intramolecular carboxylate ester-phenol H-bonds (200 mM) are an order of magnitude larger than those found for phosphonate diester-phenol H-bonds (30 mM). The corresponding intermolecular phosphonate diester-phenol H-bonds are 2 orders of magnitude more stable than carboxylate ester-phenol H-bonds, and the large differences in EM may be due to some kind of compensation effect, where the stronger H-bond is harder to make, because it imposes tighter constraints on the geometry of the complex.

Pd-EDTA as an efficient catalyst for Suzuki-Miyaura reactions in water

PdCl2-EDTA complex 1 is an efficient catalyst for the Suzuki-Miyaura reactions of aryl and heteroaryl halides with aryl(heteroaryl)boronic acids in water at 20-100°C. Aryl iodides and bromides undergo the cross-coupling with turnover numbers (T

Cyclohexylcarbamic acid 3′- or 4′-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: Synthesis, quantitative structure-activity relationships, and molecular modeling studies

Fatty acid amide hydrolase (FAAH) is a promising target for modulating endocannabinoid and fatty acid ethanolamide signaling, which may have important therapeutic potential. We recently described a new class of O-arylcarbamate inhibitors of FAAH, includin

The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes

The synthesis of the titled compounds by Suzuki-Miyaura cross coupling on Merrifield resin - Leznoff acetal - linked halo benzaldehydes followed by mild acid hydrolysis is reported; synthetic utility for heterocycles based on solution phase Directed ortho Metalation chemistry is demonstrated.

Highly Selective Cross-Coupling Reactions of Aryl(halo)silanes with Aryl Halides: A General and Practical Route to Functionalized Biaryls

The palladium catalyzed cross-coupling reaction of aryl halides with aryl(halo)silanes (halogen=F, Cl) gives good yields of unsymmetrical biaryls and p-terphenyls.The reaction takes place smoothly in N,N-dimethylformamide in the presence of an appropriate palladium catalyst and potassium fluoride.Since this reaction is tolerant of a variety of reactive functional groups, highly functionalized 4,4'-, 3,4'-, 2,4'- and even sterically crowded 2,2'-disubstituted biaryls can be obtained in moderate to high yields.The synthetic utility of the method has been demonstrated by its application to a short synthesis of liquid crystals.Mechanistic aspects of transmetalation of an aryl(fluoro)silicate intermediate with a palladium complex are discussed on the basis of the substituent effects on the rate of the cross-coupling reactions.

Selective Synthesis of Unsymmetrical Biaryls via Palladium-Catalyzed Cross-Coupling of Arylfluorosilanes with Aryl Iodides

In the presence of potassium fluoride, arylfluorosilanes readily participate in Pd-catalyzed cross-coupling reaction of aryl iodides to give the corresponding unsymmetrical biaryls in good yields.