6158-54-9

Basic information

• Product Name: Benzoic acid, 4-benzoyl-, methyl ester
• Synonyms: Benzoic acid, 4-benzoyl-, methyl ester;4-Benzoylbenzoic acid methyl ester;4-Benzoylbenzoic acid methyl
• CAS NO: 6158-54-9
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Mol File: 6158-54-9.mol
• Article Data: 109

Chemical Properties

• Boiling Point: 380°C at 760 mmHg
• Flash Point: 168.8°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 5.62E-06mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Benzoic acid, 4-benzoyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-benzoyl-, methyl ester(6158-54-9)
• EPA Substance Registry System: Benzoic acid, 4-benzoyl-, methyl ester(6158-54-9)

Safety Data

• Hazardous Substances Data: 6158-54-9(Hazardous Substances Data)

Usage

General Description

Benzoic acid, 4-benzoyl-, methyl ester is an organic compound commonly used as a flavoring agent and preservative in the food and beverage industry. It is derived from benzoic acid and is a clear, colorless liquid with a pleasant aroma. It is also used in the production of various fragrances and perfumes. In addition, it is utilized in the manufacturing of pharmaceuticals and as a precursor in organic synthesis. However, it is important to handle this chemical with caution as it can be harmful if ingested or inhaled in large quantities.

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 
• 201230-82-2 carbon monoxide 
• 619-44-3 methyl 4-iodobenzoate 
• 383-35-7 ethyldifluorophenylsilane 
• 934-56-5 trimethyl(phenyl)stannane 
• 98-88-4 benzoyl chloride 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 100-58-3 phenylmagnesium bromide 
• 71-43-2 benzene 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 591-50-4 iodobenzene 

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 
• 1185259-44-2 1-[(4-methoxycarbonyl)phenyl]-1-phenylmethanone p-tolylsulfonylhydrazone 
• 1252782-19-6 methyl 4-(2-phenyl-1,3-dithiolan-2-yl)benzoate 
• 1252782-20-9 methyl 4-(difluoro(phenyl)methyl)benzoate 

Relevant articles and documents

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

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.

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.