1871-36-9

Usage

Uses

Used in Pharmaceutical and Fragrance Industries:
2,6-Xylyl benzoate is used as an intermediate in the synthesis of various chemicals, playing a crucial role in the production of pharmaceuticals and fragrances. Its chemical structure allows for the creation of a diverse range of compounds with specific therapeutic or aromatic properties.
Used in Plastics and Coatings Industry:
2,6-Xylyl benzoate is used as a UV stabilizer for plastics and coatings, capitalizing on its ability to absorb and dissipate ultraviolet radiation. This application helps protect materials from degradation and fading caused by exposure to sunlight, thereby enhancing their durability and longevity.
Used in Electronics and Display Technologies:
2,6-Xylyl benzoate is a key component in the production of liquid crystals, which are extensively utilized in electronics and display technologies. Its inclusion in liquid crystal formulations contributes to the performance and quality of devices such as television screens, computer monitors, and smartphone displays.

InChI:InChI=1/C15H14O2/c1-11-7-6-8-12(2)14(11)17-15(16)13-9-4-3-5-10-13/h3-10H,1-2H3

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 100-52-7 benzaldehyde 
• 10533-83-2 N-benzoyl-N-methyl-4-methylbenzenesulfonamide 
• 101137-69-3 tert-butyl benzoyl(phenyl)carbamate 
• 58585-84-5 1,3-dioxoisoindolin-2-yl benzoate 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 81912-53-0 4(S)-(methoxycarbonyl)-N-benzoyl-1,3-oxazolidine-2-thione 
• 81925-64-6 methyl 3-benzoyl-2-thioxothiazolidine-4-carboxylate 

Downstream Products

• 7440-31-5 tin 
• 98217-98-2 Bu₃Sn(o2,6-Me₂C₆H₃) 
• 4342-36-3 (Benzoyloxy)tributylstannan 
• 93-58-3 benzoic acid methyl ester 
• 404947-48-4 (4-allylhepta-1,6-dien-4-yl) benzene 
• 61400-67-7 4-phenylmethylene-2,6-dimethyl-2,5-cyclohexadien-1-one 
• 854858-38-1 acetic acid-(4-benzyl-2,6-dimethyl-phenyl ester) 
• 41772-31-0 4‐benzyl‐2,6‐dimethylphenol 
• 5336-56-1 (4‐hydroxy‐3,5‐dimethylphenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Synthesis, characterization, docking study and antimicrobial activity of 2-(4-benzoylphenoxy)-1-[2-(1-methyl-1H-indol-3-yl)methyl)-1H-benzo[d]imidazol-1-yl] ethanone derivatives

The occurrence of drug-resistant bacterial infections impulses the development of new antibacterial agents that own a mechanism of action different from traditional antibiotics. From the earlier days, benzophenone, indole and benzimidazole moieties alone

Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides

Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Nickel-Catalyzed Cross-Coupling of Aryl Redoxactive Esters with Aryl Zinc Reagents

A nickel-catalyzed aryl-aroyloxyl C(sp2)-O radical cross-coupling reaction conducted using a redox active ester with aryl zinc reagent was developed. This method demonstrates a new disconnection approach for formation of aryl aryl esters. In the one-pot sequential process, the readily available aryl carboxylic acids can be converted into functionalized aryl aryl esters and heteroaryl esters. This protocol is amenable to the gram-scale synthesis. The present method has a wide substrate scope and high functional group tolerance.

Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions

A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.

Transition-Metal-Free Poly(thiazolium) Iodide/1,8-Diazabicyclo[5.4.0]undec-7-ene/Phenazine-Catalyzed Esterification of Aldehydes with Alcohols

Poly(3,4-dimethyl-5-vinylthiazolium) iodide was used as a polymer precatalyst in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and phenazine for the oxidative esterification of aldehydes with alcohols. Selective functionalization of OH groups was achieved in the presence of NH2 groups. The poly(thiazolium) iodide/DBU/phenazine system exhibited excellent catalytic activity and could be reused five times without loss of activity.

Copper-catalyzed silylation of p-quinone methides: New entry to dibenzylic silanes

An efficient and general copper(i)-catalyzed silylation of p-quinone-methides is described. Non-symmetric dibenzylic silanes are obtained in high yields under mild reaction conditions. These compounds can be used as bench-stable benzylic carbanion precursors.

Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors

A series of 2-(4-benzoyl-phenoxy)-N-(4-phenyl-thiazol-2-yl)-Acetamides (10a-n) were synthesized by multistep reaction sequence and all the compounds were well characterized for structural elucidation. The in vitro cytotoxicity of compounds 10a-n was evaluated against EAC and DLA cell lines using trypan blue dye exclusion method. Further MTT assay and LDH release assay, followed by in vivo studies on murine model were also evaluated. The compound 10h with a methyl and fluoro groups at benzophenone moiety and methoxy group at phenyl ring was in a leading position to exhibit the promising antiproliferative effect through translational VEGF-A inhibition.

Design, synthesis, and anticancer properties of novel benzophenone- conjugated coumarin analogs

In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a-o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation-7 (MCF-7) and Ehrlich's ascites tumor (EAT) cell lines and their biomarkers, followed by in silico studies regarding phosphoinositide 3-kinase (PI3K) and caspase by molecular docking. Benzophenones have been reported as potential drugs targeting tumor angiogenesis; thus, the formation of neovessels in an in vivo model system like CAM, which is angiogenesis dependent, was observed in the presence of compounds 8a-o. The above findings would help in understanding their putative potential as therapeutic agents for cancer patients. Coumarin-integrated benzophenone conjugates (8a-o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF-7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3-kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system.

O-acylation of substituted phenols with various alkanoyl chlorides under phase-transfer catalyst conditions

Esterification of several types of mono-and disubstituted phenols with various mono-and dialkanoyl chlorides was performed in phase-transfer catalysis conditions, using tetrabutylammonium chloride in a mixture of aqueous NaOH and dichloromethane. The process is particularly efficient (almost quantitative yields) as well as rapid (only 5 min reaction time, at a temperature of0°C). Taylor & Francis Group, LLC.