85-55-2

Usage

Uses

Used in Chemical Synthesis:
2-(4-Methylbenzoyl)benzoic acid is used as a reactant in the coupling of benzoic and phenylacetic acids with aryltrifluoroborates. This reaction is an important step in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. The use of aryltrifluoroborates as coupling partners allows for mild reaction conditions and high selectivity, making this method a valuable tool in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-Methylbenzoyl)benzoic acid can be used as a key intermediate in the synthesis of various drug molecules. Its unique structure and functional groups make it a promising candidate for the development of new drugs with improved therapeutic properties. For example, it can be used in the synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs), which are widely used to treat pain, inflammation, and fever.
Used in Agrochemical Industry:
2-(4-Methylbenzoyl)benzoic acid can also be utilized in the agrochemical industry for the development of new pesticides and herbicides. Its chemical properties allow it to be incorporated into the molecular structures of these compounds, potentially enhancing their efficacy and selectivity against target pests and weeds.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2-(4-Methylbenzoyl)benzoic acid can be employed as a building block for the synthesis of various high-value compounds, such as dyes, pigments, and fragrances. Its unique structure and reactivity make it a valuable component in the development of novel specialty chemicals with specific properties and applications.

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

Upstream product

• 85-44-9 phthalic anhydride 
• 108-88-3 toluene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 80764-40-5 [2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-p-tolyl-methanone 
• 7446-70-0 aluminium trichloride 
• 4397-55-1 phthalic monoacid monomethyl ester chloride 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 65-85-0 benzoic acid 
• 13740-72-2 4-(1-oxo-3-p-tolyl-inden-2-yl)-benzenesulfonyl chloride 
• 13304-46-6 2-phenyl-3-(p-tolyl)-1H-inden-1-one 
• 874-60-2 4-methyl-benzoyl chloride 
• 27331-34-6 1-(4-methylphenyl)naphthalene 
• 64-19-7 acetic acid 
• 21615-75-8 3-(4-tolyl)-isobenzofuranone 

Downstream Products

• 6424-25-5 methyl 2-(4-methylbenzoyl)benzoate 
• 117157-59-2 3-acetoxy-3-p-tolyl-phthalide 
• 75654-05-6 4'-methyl-o-benzoylbenzoic acid chloride 
• 57709-79-2 1-oxo-2-(4-nitrophenyl)-4-(4-tolyl)-1,2-dihydrophthalazine 
• 121561-19-1 2,4-dinitrophenylhydrazone of 2-(4-toluoyl)benzoic acid 
• 143390-61-8 9b-p-tolyl-2,3-dihydro-9bH-thiazolo[2,3-a]isoindol-5-one 
• 134-84-9 4-Methylbenzophenone 
• 84-54-8 2-methylanthracene-9,10-dione 
• 15254-27-0 2-(3-chloro-4-methyl-benzoyl)-benzoic acid 

Relevant academic research and scientific papers

2-(p-Toluoyl)benzoic acid

The title compound, C15H12O3, crystallizes as a centrosymmetric dimer hydrogen bonded via the carboxylic acid groups. The carboxylic acid group is nearly coplanar with the adjacent aromatic ring, which is almost perpendicular to the tolyl ring. In contrast to all comparable o-benzoylbenzoic acid structures retrieved from the Cambridge Structural Database, the torsion angle between the carbonyl group linking both aromatic rings and the phenyl ring carrying the carboxylic acid group is less than 90°, resulting in a shorter distance between the two carbonyl O atoms.

Construction of an isoquinolinone framework from carboxylic-ester-directed umpolung ring opening of methylenecyclopropanes

An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to realize an umpolung ring opening of the MCP. This work established an operationally convenient protocol for the rapid construction of isoquinolinone frameworks. This journal is

(E)-2-Styrylanthracene-9,10-dione: A new type of fluorescent probe core and its application in specific mitochondria imaging

Herein, a new type of fluorescent probe core, (E)-2-styrylanthracene-9,10-dione (EK01), was developed which displayed strong fluorescence quantum yield (Φ = 0.867 in DMF; Φ = 0.561 in acetone; Φ = 0.616 in CH2Cl2; Φ = 0.265 in DMSO), good photostability, large stokes shift (90 nm–120 nm) and molar extinction coefficients (0.5875 × 104–0.7609 × 104 mol?1 L cm?1). During cell assays and co-localization experiments, EK01 showed excellent cell membrane permeability and low cytotoxicity against MCF-10A (human mammary epithelial cell line) and HT-29 (human colorectal adenocarcinoma cell line). Particularly, we surprisingly discovered that EK01 could selectively aggregate in mitochondria and specific stain it in a green emissive fluorescent form, which means that EK01 could be a real-time specifically monitor of mitochondria in living cells with a high signal-to-noise ratio. Hence a new mitochondria imaging method was established which is incubating EK01 with living cells for 1 h at a final concentration of 6–12 μM, then visualizing under a confocal microscope at 395 nm. It is worth noting that the fluorescence efficiency of EK01 is not outstanding in organisms, it has much stronger fluorescence efficiency in other organic solvent systems (such as DMF, acetone and CH2Cl2). Therefore, as a new type of fluorescent core that is easy to synthesis and graft, we believe that (E)-2-styrylanthracene-9,10-diones have the potential to develop a variety of fluorescence platforms applying in different fields.

Friedel - gram acylating reaction method based on phthalic anhydride and aromatic alkyl compound

A part of a substituted alkylbenzene is used as a solvent and a reaction raw material for - gram acylating reaction, a part of a substituted alkylbenzene is dissolved in a reaction raw material phthalic anhydride and a chloroaluminate ionic liquid catalyst, and a residual part of a substituted alkylbenzene is added dropwise - to obtain - (2 - 4' - alkylbenzoyl) benzoic acid intermediate. 2 -position positioning selectivity of the method is higher, and the reaction production cost is low.

Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof

The invention relates to a tetracyano-anthraquinone dimethane micromolecular acceptor material as well as a preparation method and application thereof. The structure of the acceptor material is as shown in a formula I, which is described in the specification. The micromolecular acceptor material has good solubility and stability, the absorption spectrum is well matched with the solar spectrum, andthe micromolecular acceptor material can be used for organic solar cells.

Mechanochemical Friedel-crafts acylations

Friedel-Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors

The presence of salicylic acid (10 mol-%) and H2O (10 equiv.) significantly improves the arylation-lactonization sequence of γ-alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ-disubstituted butyrolactones. The protocol is user-friendly and can be used at gram-scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.

Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors

A series of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives (1a–j) was designed and synthesized as novel xanthine oxidase inhibitors. Among them, the L/D-phenylalanine derivatives (1d and 1i) and the L/D-tryptophan derivatives (1e and 1j) were effective with micromolar level potency. In particular, the L-phenylalanine derivative 1d (IC50?=?3.0?μm) and the D-phenylalanine derivative 1i (IC50?=?2.9?μm) presented the highest potency and were both more potent than the positive control allopurinol (IC50?=?8.1?μm). Preliminary SAR analysis pointed that an aromatic amino acid fragment, for example, phenylalanine or tryptophan, was essential for the inhibition; the D-amino acid derivative presented equal or greater potency compared to its L-enantiomer; and the 9,10-anthraquinone moiety was welcome for the inhibition. Molecular simulations provided rational binding models for compounds 1d and 1i in the xanthine oxidase active pocket. As a result, compounds 1d and 1i could be promising lead compounds for further investigation.

Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors

A series of (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesized and identified as novel xanthine oxidase inhibitors. Among them, the most promising compounds 1h and 1k were obtained with IC50values of 0.6?μM and 0.8?μM, respectively, which were more than 10-fold potent compared with allopurinol. The Lineweaver-Burk plot revealed that compound 1h acted as a mixed-type xanthine oxidase inhibitor. SAR analysis showed that the benzaldehyde moiety played a more important role than the anthraquinone moiety for inhibition potency. The basis of significant inhibition of xanthine oxidase by 1h was rationalized by molecular modeling studies.

2 - substituted - 9, 10 - anthraquinone compound, preparation method and use thereof

The invention belongs to the technical field of medicine, and particularly relates to 2-substituted-9,10-anthraquinone compounds represented by the general formula I, the general formula II, the general formula III and the general formula IV, and pharmaceutically acceptable salts, hydrates or solvates and pharmaceutically acceptable carriers thereof. A preparation method comprises the steps: with phthalic anhydride as a starting material, carrying out a Friedel-Crafts reaction, concentrated sulfuric acid dehydration, NBS bromization and sodium azide substitution, generating a key intermediate 2-azide methyl-9,10-anthraquinone, and finally in the presence of copper sulfate pentahydrate and vitamin C, carrying out a Husigen cycloaddition reaction with substituted alkyne; or carrying out concentrated sulfuric acid dehydration, cyclization, chromium trioxide oxidation and thionyl chloride chlorination, to obtain anthraquinone-2-formyl chloride, then carrying out an acylation reaction with various L-amino acid methyl esters, further hydrolyzing, and thus obtaining the target compounds. The prepared compounds show good results in in-vitro antitumor activity tests.