6158-54-9

Usage

Uses

Used in Food and Beverage Industry:
Benzoic acid, 4-benzoyl-, methyl ester is used as a flavoring agent and preservative for its ability to extend the shelf life of food and beverages by inhibiting the growth of microorganisms.
Used in Fragrance and Perfume Industry:
Benzoic acid, 4-benzoyl-, methyl ester is used as a key ingredient in the production of various fragrances and perfumes due to its pleasant aroma.
Used in Pharmaceutical Industry:
Benzoic acid, 4-benzoyl-, methyl ester is utilized in the manufacturing of pharmaceuticals, where it plays a role in the development and formulation of medications.
Used in Organic Synthesis:
Benzoic acid, 4-benzoyl-, methyl ester serves as a precursor in organic synthesis, contributing to the creation of other chemical compounds and products.
Safety Precautions:
It is important to handle Benzoic acid, 4-benzoyl-, methyl ester with caution, as it can be harmful if ingested or inhaled in large quantities. Proper safety measures should be taken during its use and storage to minimize potential risks.

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

Upstream product

• 611-95-0 4-carboxybenzophenone 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 24650-42-8 2,2-dimethoxy-2-phenylacetophenone 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 100-58-3 phenylmagnesium bromide 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 619-44-3 methyl 4-iodobenzoate 
• 98-80-6 phenylboronic acid 
• 1571-08-0 methyl 4-formylbenzoate 
• 1538-62-1 triphenylantimony(V) diacetate 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Downstream Products

• 183235-14-5 4-benzoylbenzanilide 
• 23450-30-8 methyl 4-benzylbenzoate 
• 540727-45-5 4-carboxybenzhydrol 
• 108419-11-0 4,4'-<1,2-Dihydroxy-1,2-diphenyl-1,2-etandiyl>bis(benzoesaeuremethylester) 
• 108419-03-0 methyl 4-(hydroxyphenylmethyl)benzoate 
• 142182-43-2 4-Vinyl-4'-chloromethyl diphenylmethane 
• 142182-42-1 4-Vinyl-4'-hydroxymethyl diphenylmethane 
• 142182-40-9 4-Formyl-4'-methoxycarbonyl diphenylmethane 
• 142182-41-0 4-Vinyl-4'-methoxycarbonyl diphenylmethane 
• 129136-15-8 4-methoxycarbonylbenzophenone dimethylacetal 
• 916171-18-1 Methyl 4-[phenyl(3,3,5,5-tetramethylcyclohexylidene)methyl]benzoate 
• 1616844-72-4 methyl 4-(2-phenyl-1,3-dioxolan-2-yl)benzoate 
• 1616844-73-5 methyl 4-(phenyl((tetrahydro-2H-pyran-2-yl)oxy)methyl)benzoate 
• 29265-82-5 p-methoxycarbonyl-1,1-diphenylethylene 

Relevant academic research and scientific papers

Quenching of Aromatic Ketone Phosphorescence by Simple Alkenes: An Arrhenius Study

The phosphorescence of 4-carboxymethylbenzophenone in carbon tetrachloride solution is quenched by various alkenes.The kinetics follow Stern-Volmer kinetics.An Arrhenius plot of kir, the apparent second-order rate constant, yields activation en

Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage

Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe

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.

COMPLEXES OF N-HETEROCYCLIC CARBENES FOR TRANSITION METAL CATALYSIS

Described herein is a new class of highly active Pd(II)-NHC complexes bearing anilines as throw-away ligands. These catalysts are well-defined, air- and moisture-stable and can be easily purified by chromatographic techniques. High activity and generality has been exemplified in the Suzuki-Miyaura cross-coupling by C-N, C-O and C-Cl cleavage. Facile syntheses of these catalysts is also described.

Pd-Catalysed carbonylative Suzuki-Miyaura cross-couplings using Fe(CO)5under mild conditions: generation of a highly active, recyclable and scalable ‘Pd-Fe’ nanocatalyst

The dual function and role of iron(0) pentacarbonyl [Fe(CO)5] has been identified in gaseous CO-free carbonylative Suzuki-Miyaura cross-couplings, in which Fe(CO)5supplied COin situ, leading to the propagation of catalytically active Pd-Fe nanoparticles. Compared with typical carbonylative reaction conditions, CO gas (at high pressures), specialised exogenous ligands and inert reaction conditions were avoided. Our developed reaction conditions are mild, do not require specialised CO high pressure equipment, and exhibit wide functional group tolerance, giving a library of biaryl ketones in good yields.

Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand

We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.

Protocol for Palladium/ N-Heterocyclic Carbene-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation

Amides are among the most important and ubiquitous functional groups in organic chemistry and process development. In this Practical Synthetic Procedure, a protocol for the Suzuki-Miyaura cross-coupling of amides by selective N-C(O) bond activation catalyzed by commercially available, air-and moisture-stable palladium/N-heterocyclic carbene (NHC) complexes is described. The procedure described involves [Pd(IPr)(cin)Cl] [IPr = 2,6-(diisopropylphenyl)imidazol-2-ylidene, cin = cinnamyl] at 0.10 mol% at room temperature and is performed on decagram scale. Furthermore, a procedure for the synthesis of amide starting materials is accomplished via selective N-tert-butoxycarbonylation, which is the preferred method over N-Acylation. The present protocol carries advantages of operational simplicity, commercial availability of catalysts, and excellent conversions at low catalyst loadings. The method is generally useful for activation of N-C(O) amide bonds in a broad spectrum of amide precursors. The protocol should facilitate the implementation of amide cross-coupling reactions.

Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions

We report the synthesis, characterization, and reactivity of [(NHC)PdCl2(aniline)] complexes. These well-defined, air- and moisture-stable catalysts are highly active in the Suzuki-Miyaura cross-coupling of amides by N-C(O) activation as well as in the Suzuki-Miyaura cross-coupling of esters, aryl chlorides, and Buchwald-Hartwig amination. Most crucially, this study introduces broadly available anilines as stabilizing ligands for well-defined Pd(II)-NHC catalysts. The availability of various aniline scaffolds, including structural and electronic diversity, has a significant potential in fine-tuning of challenging cross-couplings by Pd-NHCs. The parent catalyst in this class, [Pd(IPr)(AN)Cl2], has been commercialized in collaboration with Millipore Sigma, offering broad access for reaction screening and optimization.

Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications

Treatment of tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized by one acetonitrile ligand. Complexes 2 and 3 were tested in several cross coupling reactions showing high conversions under low catalyst loadings and mild reaction conditions. Additionally, complexes 2 and 3 performed well in the hydrosilylation of terminal alkynes with good selectivity toward the E-isomer.

Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions

The development of efficient methods for facilitating N-C(O) bond activation in amides is an important objective in organic synthesis that permits the manipulation of the traditionally unreactive amide bonds. Herein, we report a comparative evaluation of a series of cyclic amides as activating groups in amide N-C(O) bond cross-coupling. Evaluation of N-acyl-imides, N-acyl-lactams, and N-acyl-oxazolidinones bearing five- and six-membered rings using Pd(II)-NHC and Pd-phosphine systems reveals the relative reactivity order of N-activating groups in Suzuki-Miyaura cross-coupling. The reactivity of activated phenolic esters and thioesters is evaluated for comparison in O-C(O) and S-C(O) cross-coupling under the same reaction conditions. Most notably, the study reveals N-acyl-δ-valerolactams as a highly effective class of mono-N-acyl-activated amide precursors in cross-coupling. The X-ray structure of the model N-acyl-δ-valerolactam is characterized by an additive Winkler-Dunitz distortion parameter ?(τ+χN) of 54.0°, placing this amide in a medium distortion range of twisted amides. Computational studies provide insight into the structural and energetic parameters of the amide bond, including amidic resonance, N/O-protonation aptitude, and the rotational barrier around the N-C(O) axis. This class of N-acyl-lactams will be a valuable addition to the growing portfolio of amide electrophiles for cross-coupling reactions by acyl-metal intermediates.