85-52-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzoylbenzoic acid is used as a reagent for the synthesis of BzATP Triethylammonium Salt, a selective P2X purinergic agonist. It is utilized in this capacity due to its ability to enhance the potency of ATP at homodimeric P2X7 receptors, making it a valuable component in the development of pharmaceuticals targeting these receptors.

Synthesis

In the presence of aluminum trichloride, phthalic anhydride and benzene are condensed and obtained by hydrolysis. The hydrochloric acid gas by-product in the reaction should preferably be absorbed into dilute hydrochloric acid for subsequent use. The industrial benzoylbenzoic acid is white to beige powder, the purity is above 97%, and the initial melting point of the dry product is ≥126.0%.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 2758, 1948 DOI: 10.1021/ja01188a035The Journal of Organic Chemistry, 39, p. 2051, 1974 DOI: 10.1021/jo00928a016

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

Recrystallise the acid from *C6H6 or cyclohexane, but it is best recrystallised by dissolving in a small volume of hot toluene and then adding just enough pet ether to cause turbidity, and cool. Dry it in a low vacuum at 80o. It can be sublimed at 230-240o/0.3mm [Bray et al. J Chem Soc 265 1957]. The S-benzylisothiuronium salt has m 177-178o (from EtOH). [Lewenz & Serijan J Am Chem Soc 75 4087 1953, Beilstein 10 H 747, 10 IV 2977.]

InChI:InChI=1/C14H10O3/c15-13(10-6-2-1-3-7-10)11-8-4-5-9-12(11)14(16)17/h1-9H,(H,16,17)/p-1

Upstream product

• 85-44-9 phthalic anhydride 
• 108-86-1 bromobenzene 
• 2674-04-6 diphenyl cadmium 
• 71-43-2 benzene 
• 5398-11-8 3-phenylphthalide 
• 792-68-7 1,2-dibenzylbenzene 
• 713-36-0 2-benzyltoluene 
• 131-58-8 2-Methylbenzophenone 
• 789-24-2 9-Phenylfluorene 
• 26486-96-4 2-ethyl-3-hydroxy-3-phenyl-2,3-dihydroisoindol-1-one 
• 37758-27-3 2-bromo-3-phenyl-1-indanone 
• 37774-78-0 2-cyanobenzophenone 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 

Downstream Products

• 606-28-0 methyl o-benzoylbenzoate 
• 67031-57-6 2-benzoyl-benzoic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 7335-63-9 3-methoxy-3-phenyl-phthalide 
• 107796-81-6 3-ethyl-3-phenylisobenzofuran-1(3H)-one 
• 604-63-7 2-benzoyl-benzoic acid-(2-ethoxy-ethyl ester) 
• 94879-71-7 3-phenyl-3-o-tolyl-3H-isobenzofuran-1-one 
• 18019-56-2 3-methyl-3-phenylphthalide 
• 141034-37-9 3-phenyl-3-(2-hydroxy-5-methylphenyl)phthalide 
• 52237-00-0 3-phenyl-3-(2,4,6-trihydroxy-phenyl)-phthalide 
• 24818-41-5 3-(naphthalen-1-yl)-3-phenylisobenzofuran-1(3H)-one 
• 596-29-2 3,3-diphenyl-2-benzofuran-1(3H)-one 
• 125416-11-7 2-benzoyl-benzoic acid octyl ester 
• 604-61-5 ethyl 2-benzoylbenzoate 
• 60456-75-9 1,1'-diphenyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione 

Relevant academic research and scientific papers

Deep compositional understanding of TBA: AlCl3 ionic liquid for its applications

Chloroaluminate ionic liquids (ILs) have been immensely used as homogeneous catalyst in Friedel-Crafts reaction. We have recently synthesized chloroaluminate ILs by reacting aluminium chloride with a hydrophobic neutral ligand i.e. tributylamine (TBA:AlCl3). The current study elaborates on the investigations of the composition of the ionic liquids at various stages of their formation. The ionic liquids were synthesized using various mole ratios of tributyl amine and aluminium chloride in range of 1:1 to 1:2.3, in presence of an aromatic solvent in a one pot reaction. Various characterization techniques like Mass spectrometry, 27Al Nuclear Magnetic Resonance, 31P Nuclear Magnetic Resonance and Fourier Transform Infrared spectroscopy were used to elucidate the formation of various moieties of the TBA:AlCl3 Ionic Liquid. This study also elaborates on the investigations of the cationic and anionic moieties and their structure-property relationship for various applications. Various Friedel-Crafts reaction of industrial importance were performed using the ionic liquid having (Al2Cl7)?moiety to assess its performance and compared with conventional processes. The synthesized products were characterised by sophisticated analytical techniques like 1H NMR, 13C NMR, FTIR, GC–MS, GC-FID, to name a few. This class of ionic liquids also have importance in various electrochemical applications like aluminium deposition and aluminium batteries.

Palladium-Catalyzed Decarboxylative ortho-C(sp2)?H Aroylation of N-Sulfoximine Benzamides at Room Temperature

A palladium-catalyzed method for the decarboxylative ortho C?H acylation of N-sulfoximine benzamides is developed at room temperature. The catalytic method enables easy access to various functionalized 2-aroylaromatic carboxylic acid derivatives in good isolated yields. Based on our mechanistic studies, a Pd(II)/Pd(IV) catalytic cycle that involves aroyl radical intermediate is proposed for the reaction.

Dibenzo[b,e]aza-6,11-diketotriazole compound as well as preparation method and application thereof

The invention provides a dibenzo[b,e]aza-6,11-diketotriazole compound and a preparation method thereof, belongs to the technical field of medicines, and specifically relates to a 5-((1-(R-phenyl)-1H-1,2,3-triazol-4-yl)methyl)-5H-dibenzo[b,e]aze-6,11-diketone anti-tumor compound as well as a preparation method and application thereof. The compound prepared by the invention has a function of inhibiting tumor activity and has excellent application prospect in the field of design, research and development of anti-tumor drugs; in addition, the preparation method is simple and easy to industrialize.

A facile greener synthesis, antimicrobial evaluation and molecular modelling of new 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-one derivatives

Abstract: The synthesis of 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-ones was performed by cyclization of 2-hydrazinyl-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine with 2-aroylbenzoic acids in ethanol containing a catalytic amount of concentrated sulfuric acid under solid state conditions. All these synthesized compounds (8a–h) were screened for their in vitro antibacterial activity against gram-positive bacteria such as (Staphylococcus aureus) and gram-negative bacteria (Escherichia coli) and also evaluated for their antifungal activity against Aspergillus Niger and Helmenthosphorium oryzae fungal strains. Some of the products demonstrate good antibacterial activity and moderate antifungal activity. In predominantly, 8b, 8d, 8g, and 8h compounds showed good to excellent antibacterial and antifungal activities. The antimicrobial activity of the compound 8 was further investigated with the help of in LibDock score docking study to predict the active sites. Graphical abstract: [Figure not available: see fulltext.].

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.

Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides

Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.

COMPOUNDS FOR TREATING PARASITIC INFECTIONS

Compounds and compositions comprising them are provided. The compounds and compositions are useful for inhibiting transport of heme across membranes in parasitic heme auxotrophic organisms, thereby limiting their growth or killing the parasites.

Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti-Inflammatory and Anti-Proliferative Agents

The chemistry of phthalazine derivatives has been of increasing interest since many of these compounds have found many chemotherapeutic applications. So this study aims to synthesize a library of phthalazine derivatives and to investigate their anti-inflammatory and anti-proliferative activities. Sixteen new phthalazinone derivatives (2a-p) were synthesized and tested for their in vitro antiproliferative and in vivo anti-inflammatory activities. All the synthesized compounds were identified and characterized by IR, 1H NMR, 13C NMR spectroscopy, and MS. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib in the carrageenan-induced rat paw edema model at 3 and 5 h, respectively. Three compounds (2h, 2j, and 2g) showed moderate sensitivity toward the renal cancer cell line UO-31. A library of new phthalazone compounds (2a-p) was synthesized as dual inhibitors (COX-2/LOX-5) and evaluated for their anti-inflammatory, anticancer activities. Two compounds showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib, whereas three compounds showed moderate sensitivity toward the renal cancer cell line UO-31.

Preparation method of synthetic anthraquinone

The invention discloses a preparation method of synthetic anthraquinone; the preparation method of synthetic anthraquinone comprises the following steps: step 1, polymerization: mixing phthalic anhydride, benzene and aluminum trichloride, and carrying out a reaction for 0.5-2 hr at the temperature of 50-70 DEG C; step 2, acidizing hydrolysis: adding sulfuric acid and water into the reactant obtained in the step 1, heating to reflux, and distilling to remove free benzene completely; and adding an organic solvent and water for diluting, precipitating o-benzoylbenzoic acid, filtering and washing with water; step 3, ring closing: taking the filter cake obtained in the step 2, carrying out dewatering treatment, adding concentrated sulfuric acid or fuming sulfuric acid, heating up to 130-135 DEG C, carrying out a heat preservation reaction for 0.5-2 hr, and dewatering to close ring; and step 4, carrying out purification treatment of the reactant obtained in the step 3, to obtain the synthetic anthraquinone pure product, wherein the organic solvent is selected from isopropyl alcohol or ethyl acetate, and has the effect of reducing the content difference of dry products of o-benzoylbenzoic acid.

Synthetic method for benzisoxazocine hydrochloride pharmaceutical intermediate--o-benzoylbenzoic acid

The invention provides a synthetic method for a benzisoxazocine hydrochloride pharmaceutical intermediate--o-benzoylbenzoic acid. The synthetic method comprises the following steps: adding 0.88 mol of 2-carboxyl-benzyl alcohol and 700 to 800 ml of phenol into a reaction vessel provided with a stirrer, a thermometer and a reflux condenser, controlling a stirring speed in a range of 130 to 170 rpm, adding 1.9 mol of cuprous chloride in batches, after the completion of addition, increasing a solution temperature to 80 to 85 DEG C, controlling reaction time in a range of 5 to 6 h, reducing a solution temperature to 35 to 40 DEG C, pouring reaction liquid into 1.3 L of a phosphoric acid solution, reducing a solution temperature to 5 to 7 DEG C, controlling a stirring speed in a range of 190 to 230 rpm so as to precipitate a white solid, then carrying out filtering, carrying out washing with a potassium bromide solution, dissolving an obtained filtered substance in a sodium sulfite solution, carrying out decolorizing with a molecular sieve, adding an oxalic acid solution until the pH value of the solution is 3 to 4 so as to precipitate a solid, reducing a solution temperature to 5 to 7 DEG C, carrying out filtering, carrying out washing with a salt solution, and carrying out drying under a temperature of 75 to 80 DEG C so as to obtain o-benzoylbenzoic acid.