22711-21-3

Usage

Uses

Used in Pharmaceutical Industry:
P-METHOXYBENZIL is used as a building block for the synthesis of various drug molecules due to its versatile reactivity and structural properties. It serves as a versatile intermediate in the development of new pharmaceutical compounds, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
P-METHOXYBENZIL is also utilized as an intermediate in the production of agrochemicals, playing a crucial role in the synthesis of various agricultural chemicals that help improve crop yield and protect plants from pests and diseases.
Used in Organic Synthesis:
As a member of the aromatic ketones class, P-METHOXYBENZIL is employed in organic synthesis for the preparation of a wide range of chemical compounds. Its unique structure and reactivity make it a valuable component in the synthesis of various organic molecules, including fine chemicals and specialty chemicals.

InChI:InChI=1/C15H12O3/c1-18-13-9-7-12(8-10-13)15(17)14(16)11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 1889-84-5 4'-methoxybenzoin 
• 4254-17-5 4-methoxybenzoin 
• 1889-77-6 2-bromo-1-(4-methoxy-phenyl)-2-phenyl-ethanone 
• 7380-78-1 4-(phenylethynyl)anisole 
• 6968-77-0 3-(4-methoxyphenyl)-2-phenylacrylic acid 
• 38828-29-4 α-benzoyloxy-4-methoxy-deoxybenzoin 
• 1694-22-0 (E)-2-(4-methoxyphenyl)-3-phenylacrylic acid 
• 103-82-2 phenylacetic acid 
• 100-66-3 methoxybenzene 
• 157894-11-6 1-(4-methoxyphenyl)-2-phenyl-2-(2,6-xylylimino)ethanone 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 3580-75-4 2-diazo-1-[4-(methyloxy)phenyl]-2-phenylethanone 
• 36913-91-4 nonaflyl anhydride 

Downstream Products

• 33705-72-5 5-(4-methoxy-phenyl)-4-phenyl-2-thiophen-2-yl-1H-imidazole 
• 100899-15-8 5-(4-methoxyphenyl)-5-phenyl-2-thiohydantoin 
• 53448-82-1 1,4-diphenyl-2-(4-mrthoxyphenyl)but-2-ene-1,4-dione 
• 17816-50-1 5-(4-methoxyphenyl)-5-phenylimidazolidine-2,4-dione 
• 17816-37-4 3a-(4-methoxy-phenyl)-6a-phenyl-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione 
• 69643-30-7 C₂₁H₃₀N₂OSi₂ 
• 93-89-0 benzoic acid ethyl ester 
• 94-30-4 ethyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Structural Effects in Photoepoxidation Sensitized by α-Diketones

A series of α-diketones and benzils were examined for their effectiveness as sensitizers in the photoepoxidation reaction.The reduction potentials of these α-diketones were also determined at a hanging-mercury-drop electrode.The reduction potentials of the p,p'-disubstituted-benzils were successfully correlated to the sum of the Hammett ? values.No evidence could be found that electron transfer plays an important role in the epoxidation mechanism.The mechanistic possibilities are briefly discussed.Studies of the photoepoxidation reaction in a variety of solvents have also shown that the reaction is very insensitive to solvent effects.

Antibody-Catalyzed Benzoin Oxidation as a Mechanistic Probe for Nucleophilic Catalysis by an Active Site Lysine

Aldolase antibody 24H6, which was obtained by reactive immunization against a 1,3-diketone hapten, is shown to catalyze additional reactions, including H/D exchange and oxidation reactions. Comparison of the H/D exchange reaction at the α-position of a wide range of aldehydes and ketones by 24H6 and by other aldolase antibodies, such as 38C2, pointed at the significantly larger size of the 24H6 active site. This property allowed for the catalysis of the oxidation of substituted benzoins to benzils by potassium ferricyanide. This reaction was used as a mechanistic probe to learn about the initial steps of the 24H6-catalyzed aldol condensation reaction. The Hammett correlation (ρ=4.7) of log(kcat) versus the substituent constant, σ, revealed that the reaction involves rapid formation of a Schiff base intermediate from the ketone and an active site lysine residue. The rate-limiting step in this oxidation reaction is the conversion of the Schiff base to an enamine intermediate. In addition, linear correlation (ρ= 3.13) was found between log(KM) and σ, indicating that electronic rather than steric factors are dominant in the antibody-substrate binding phenomenon and confirming that the reversible formation of a Schiff base intermediate comprises part of the substrate-binding mechanism.

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.

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.

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.

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.

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.

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.

Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds

A new, general oxidative route to transformations of 1,3-dicarbonyl compounds to 1,2-dicarbonyl compounds by merging copper and I2 catalysis is described. This method is applicable to broad 1,3-dicarbonyl compounds, including 1,3-diketones, 1,3-keto esters and 1,3-keto amides. Mechanistical studies show that the reaction is achieved via the C–C bond cleavage and CO release cascades.

Synthesis of unsymmetrical benzilsviapalladium-catalysed a-arylation-oxidation of 2-hydroxyacetophenones with aryl bromides

A diverse set of unsymmetrically substituted benzils were facilely synthesised by a cross-coupling reaction between 2-hydroxyacetophenones and aryl bromides in the presence of a palladium catalyst. Experimental studies suggested a reaction mechanism involving a one-pot tandem palladium-catalysed a-arylation and oxidation, where aryl bromides play a dual role as mild oxidants as well as arylating agents.