67468-65-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyl-Benzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. It serves as a reactant for the production of benzoyl-benzylidenecyclohexanone analogs, which are dual inhibitors for acetylcholinesterase and butyrylcholinesterase. These inhibitors play a crucial role in the treatment of Alzheimer's disease and other neurodegenerative disorders by enhancing cognitive function and memory.
Additionally, 4-Benzyl-Benzaldehyde can be utilized in the development of other bioactive molecules with potential applications in the pharmaceutical industry, such as anti-inflammatory, analgesic, and antimicrobial agents.
Used in Flavor and Fragrance Industry:
Due to its strong, sweet, and floral odor, 4-Benzyl-Benzaldehyde is also used as a component in the flavor and fragrance industry. It can be found in the formulation of various perfumes, colognes, and other scented products, contributing to their unique and pleasant aromas.
Used in Chemical Research:
4-Benzyl-Benzaldehyde is a valuable compound for chemical research and development, particularly in the field of organic chemistry. It serves as a starting material for the synthesis of various complex organic molecules and can be used to study the reactivity and properties of different functional groups.

InChI:InChI=1/C14H12O/c15-11-14-8-6-13(7-9-14)10-12-4-2-1-3-5-12/h1-9,11H,10H2

Upstream product

• 100-97-0 hexamethylenetetramine 
• 14297-39-3 4-benzylbenzyl chloride 
• 100-39-0 benzyl bromide 
• 943868-13-1 4-benzylsulfanyl-2,3,5,6-tetrafluoropyridine 
• 1122-91-4 4-bromo-benzaldehyde 
• 100-53-8 phenylmethanethiol 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 28144-70-9 anthranilic acid amide 
• 1539-57-7 diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 4463-42-7 benzyl boronic acid 
• 61079-82-1 N-(phenylmethyl)-di(p-toluenesulfonyl)amine 
• 87199-17-5 4-formylphenylboronic acid, 
• 51359-78-5 4-(bromomethyl)benzaldehyde 

Downstream Products

• 103276-47-7 (4-benzyl-phenyl)-bis-(4-dimethylamino-phenyl)-methane 
• 102078-69-3 (4-benzyl-benzyliden)-aniline 
• 101596-45-6 (E)-4-(4-benzylphenyl)but-3-en-2-one 
• 121816-53-3 1t,5t-bis-(4-benzyl-phenyl)-penta-1,4-dien-3-one 
• 15866-31-6 phenyl(p-vinylphenyl)methane 
• 1159113-30-0 (4aS,4bR,5S,6aS,6bS,8R,9aR,10aS,10bS,12S)-8-(4-benzylphenyl)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a-dimethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one 
• 1365914-91-5 C₃₅H₃₆F₂O₆ 
• 60313-20-4 4-benzyl-bibenzyl-α-ol 
• 102448-48-6 (4-benzyl-benzylidene)-malonic acid diethyl ester 
• 99480-37-2 3t-(4-benzyl-phenyl)-acrylic acid 
• 100866-27-1 4-benzyl-benzaldehyde seqtrans-oxime 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C-S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Photoredox Heterobimetallic Dual Catalysis Using Engineered Covalent Organic Frameworks

The functionalization of an imine-based layered covalent organic framework (COF), containing phenanthroline units as ligands, has allowed the obtention of a heterobimetallated material. Photoactive Ir and Ni fragments were immobilized within the porous structure of the COF, enabling heterogeneous light-mediated Csp3-Csp2cross-couplings. As radical precursors, potassium benzyl- and alkoxy-trifluoroborates, organic silicates, and proline derivatives were employed, which brings out the good versatility ofIr,Ni@Phen-COF. Moreover, in all the studied cases, an enhanced activity and stability have been observed in comparison with analogous homogenous systems.

Mild environment-friendly oxidative debenzylation of N-benzylanilines using DMSO as an oxidant

Oxidative debenzylation of N-benzyl aromatic amines using DMSO as a non-toxic oxidant and catalyzed by TsOH gave Nphenylimines, which were spontaneously hydrolyzed to form anilines and benzaldehydes in good yields. This reaction employs mild, metal-free conditions. The conditions are also suitable for the debenzylation of benzylphenylethers.

Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst

The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co

HETEROCYCLIC COMPOUNDS AS MUTANT IDH INHIBITORS

The present disclosure relates generally to compounds useful in treatment of conditions associated with mutant isocitrate dehydrogenase (mt-IDH), particularly mutant IDH1 enzymes. Specifically, the present invention discloses compound of formula (IA), which exhibits inhibitory activity against mutant IDH1 enzymes. Method of treating conditions associated with excessive activity of mutant IDH1 enzymes with such compound is disclosed. Uses thereof, pharmaceutical composition, and kits are also disclosed.

Deoxygenative cross-electrophile coupling of benzyl chloroformates with aryl iodides

This work describes Ni-catalyzed cross-electrophile coupling of benzyl chloroformate derivatives with aryl iodides that generates a wide range of diaryl methane products. The mild reaction conditions merit the C-O bond radical fragmentation of benzyl chloroformates via halide abstraction or a single electron reduction by a Ni catalyst. This work offers a new substrate type for cross-electrophile couplings.

Metal-organic layers as multifunctional two-dimensional nanomaterials for enhanced photoredox catalysis

Metal-organic layers (MOLs) have recently emerged as a novel class of molecular two-dimensional (2D) materials with significant potential for catalytic applications. Herein we report the design of a new multifunctional MOL, Hf12-Ir-Ni, by laterally linking Hf12 secondary building units (SBUs) with photosensitizing Ir(DBB)[dF(CF3)ppy]2+ [DBB-Ir-F, DBB = 4,4′-di(4-benzoato)-2,2′-bipyridine; dF(CF3)ppy = 2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine] bridging ligands and vertically terminating the SBUs with catalytic Ni(MBA)Cl2 [MBA = 2-(4′-methyl-[2,2′-bipyridin]-4-yl)acetate] capping agents. Hf12-Ir-Ni was synthesized in a bottom-up approach and characterized by TEM, AFM, PXRD, TGA, NMR, ICP-MS, UV-vis, and luminescence spectroscopy. The proximity between photosensitizing Ir centers and catalytic Ni centers (～0.85 nm) in Hf12-Ir-Ni facilitates single electron transfer, leading to a 15-fold increase in photoredox reactivity. Hf12-Ir-Ni was highly effective in catalytic C-S, C-O, and C-C cross-coupling reactions with broad substrate scopes and turnover numbers of ～4500, ～1900, and ～450, respectively.