22711-23-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorobenzyl compounds are used as intermediates or building blocks in the synthesis of various pharmaceutical products. Their unique chemical structure allows them to be incorporated into drug molecules, potentially enhancing their therapeutic effects or improving their stability and bioavailability.
Used in Agricultural Chemicals:
In the agricultural sector, 4-Chlorobenzyl compounds may be utilized in the development of agrochemicals, such as pesticides or herbicides. Their chemical properties can contribute to the effectiveness of these products in controlling pests and weeds, thereby supporting crop protection and yield.
Used in Industrial Applications:
4-Chlorobenzyl compounds can also be found in various industrial applications, such as the production of dyes, plastics, or other chemical products. Their versatility in chemical reactions and potential to form new compounds make them valuable in the synthesis of a wide range of materials with specific properties and uses.

InChI:InChI=1/C14H9ClO2/c15-12-8-6-11(7-9-12)14(17)13(16)10-4-2-1-3-5-10/h1-9H

Upstream product

• 1889-71-0 4'-chloro-2-phenylacetophenone 
• 39774-18-0 p-chlorobenzoin 
• 107323-82-0 4-chlorobenzylmagnesium bromide 
• 55-21-0 benzamide 
• 1889-78-7 2-bromo-1-(4-chlorophenyl)-2-phenylethanone 
• 5172-02-1 1-chloro-4-(2-phenylethynyl)benzene 
• 1657-50-7 (E)-1-(4-chlorophenyl)-2-phenylethene 
• 71292-76-7 diethyl α-trimethylsilyloxy-α-(4-chlorobenzoyl)benzylphosphonate 
• 50793-42-5 meso-4-chlorostilbene dibromide 
• 3493-18-3 1-(4-chlorophenyl)-2-diazo-2-phenylethan-1-one 
• 74955-09-2 [2-(4-Chloro-phenyl)-[1,3]dithian-2-yl]-phenyl-methanone oxime 
• 111768-18-4 R-(-)-1-(4-chlorophenyl)-2-hydroxy-2-phenylethanone 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 36913-91-4 nonaflyl anhydride 

Downstream Products

• 6325-69-5 R,S-5-(p-Chlorphenyl)-5-phenylhydantoin 
• 38268-05-2 3-(4-chloro-phenyl)-2,4,5-triphenyl-cyclopentadienone 
• 22915-10-2 2-(4-Chlor-benzoyl)-2-phenyl-1.1-dicyanaethylen 
• 147001-10-3 R,S-5-(p-Chlorphenyl)-3,5-diphenylhydantoin 
• 133657-08-6 1-benzyl-4-(4-chlorophenyl)-5-phenylimidazole 
• 71292-81-4 2-(4-chlorophenyl)-2-hydroxy-1-phenylethanone 
• 39774-18-0 p-chlorobenzoin 
• 111768-18-4 R-(-)-1-(4-chlorophenyl)-2-hydroxy-2-phenylethanone 
• 135518-70-6 3,6-Dichloro-2-(4-dimethylsulfamoyl-phenyl)-benzofuran-4-sulfonic acid dimethylamide 
• 135490-75-4 3-Chloro-2-(4-chloro-2-dimethylsulfamoyl-phenyl)-benzofuran-6-sulfonic acid dimethylamide 
• 108511-08-6 2-(4-chlorophenyl)-1,4-diphenylbut-2-ene-1,4-dione 
• 108511-09-7 1-(4-cholorophenyl)-2,4-diphenylbut-2-ene-1,4-dione 
• 108511-07-5 3-(4-chlorophenyl)-3,5-diphenyl-2(3H)-furanone 
• 69643-29-4 1-(4-chloro-phenyl)-2-phenyl-N,N'-bis-trimethylsilanyl-ethanediylidenediamine 

Relevant academic research and scientific papers

Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones

Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.

Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.

Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi3complex with a macrocyclic tris(salen)-ligand

A hetero-tetranuclear CeNi3 complex with a macrocyclic ligand catalysed the aerobic oxygenation of a methylene group adjacent to a carbonyl group under visible-light radiation to produce the corresponding α-diketones. The visible-light induced homolysis of the Ce-O bond of a bis(enolate) intermediate is proposed prior to aerobic oxygenation.

Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation

The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Lanthanide complexes based on an anthraquinone derivative ligand and applications as photocatalysts for visible-light driving photooxidation reactions

Four isostructural lanthanide coordination complexes based on 3,7-diamino-9,10-anthraquinone-2,6-disulfonate (dianionic, L) have been synthesized by hydrothermal method, namely [Er(L)(H2O)6]?[Er(H2O)8]?2L?8H2O (Er-L), [Tm(L)(H2O)6]?[Tm(H2O)8]?2L?8.5H2O (Tm-L), [Yb(L)(H2O)6]?[Yb(H2O)8]?2L?9H2O (Yb-L), [Lu(L)(H2O)6]?[Lu(H2O)8]?2L?9H2O (Lu-L). Single-crystal X-ray analysis reveals the existence of both coordinated and free ligand L in the crystal structure. Versatile sulfonate groups on these distinct L ligands, together with very rich coordinated and lattice water molecules, form a lot of hydrogen-bonding motifs that contribute to the stabilization of the crystal packing. It is interesting that the ligands stack into columns through strong π-π interactions and the centroid-centroid distances are between 3.281 and 3.331 ?. These ligands are stacked in an alternate off-set mode to avoid the steric hindrance between the bulky sulfonate groups, generating a repeated structural unit involving six stacked ligands. These lanthanide complexes proved to be good heterogeneous photocatalyst for promoting the visible-light driving photooxidation reactions of diarylacetylenes and thioethers. The Er-L complex exhibited the best catalytic activity and showed good catalytic efficiency over a wide range of substrates for both reaction systems. The Er-L photocatalyst can be easily isolated by simple filtration as crystalline material upon completion of the photooxidation reaction without structure change, and can be recycled for at least five catalytic cycles with persistent catalytic efficiency without any need of activation or regeneration. This family of lanthanide complexes represent a category of promising heterogeneous photocatalysts in terms of green chemistry, with the potential of promoting organic transformations highly efficiently under the irradiation of visible light.

Structural insights into the desymmetrization of bulky 1,2-dicarbonyls through enzymatic monoreduction

Benzil reductases are dehydrogenases preferentially active on aromatic 1,2-diketones, but the reasons for this peculiar substrate recognition have not yet been clarified. The benzil reductase (KRED1-Pglu) from the non-conventional yeast Pichia glucozyma showed excellent activity and stereoselectivity in the monoreduction of space-demanding aromatic 1,2-dicarbonyls, making this enzyme attractive as biocatalyst in organic chemistry. Structural insights into the stereoselective monoreduction of 1,2-diketones catalyzed by KRED1-Pglu were investigated starting from its 1.77 ? resolution crystal structure, followed by QM and classical calculations; this study allowed for the identification and characterization of the KRED1-Pglu reactive site. Once identified the recognition elements involved in the stereoselective desymmetrization of bulky 1,2-dicarbonyls mediated by KRED1-Pglu, a mechanism was proposed together with an in silico prediction of substrates reactivity.

One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst

A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.

Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones

A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

1-butyl-3-methylimidazol-2-ylidene as an efficient catalyst for cross-coupling between aromatic aldehydes and N-aroylbenzotriazoles

Cross-coupling of aromatic aldehydes with N-aroylbenzotriazoles in [Bmim]Br in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) provided an efficient procedure for the synthesis of 1,2-diarylethane-1,2-diones.