85-52-9

Basic information

• Product Name: 2-Benzoylbenzoic acid
• Synonyms: OTAVA-BB BB7020401721;OBBA;O-BENZOYLBENZOIC ACID;ORTHO-BENZOYL BENZOIC ACID;2-Benzoquinonecarboxylic acid;2-benzoquinonecarboxylicacid;2-benzoyl-benzoicaci;Benzoic acid, o-benzoyl-
• CAS NO: 85-52-9
• Molecular Formula: C₁₄H₁₀O₃
• Molecular Weight: 226.23
• EINECS: 201-612-2
• Product Categories: Industrial/Fine Chemicals;Aromatic Benzophenones & Derivatives (substituted);Functional Materials;Photopolymerization Initiators
• Mol File: 85-52-9.mol
• Article Data: 43

Chemical Properties

• Melting Point: 126-129 °C(lit.)
• Boiling Point: 257-265 °C(lit.)
• Flash Point: 257°C
• Appearance: Almost white to slightly beige/Crystalline Powder
• Density: 1.2022 (rough estimate)
• Vapor Pressure: 2.17E-08mmHg at 25°C
• Refractive Index: 1.5767 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: pK1: 3.54 (25°C)
• Water Solubility: 284mg/L at 20℃
• BRN: 1107841
• CAS DataBase Reference: 2-Benzoylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzoylbenzoic acid(85-52-9)
• EPA Substance Registry System: 2-Benzoylbenzoic acid(85-52-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: DG3600000
• TSCA: Yes
• Hazardous Substances Data: 85-52-9(Hazardous Substances Data)

Usage

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%.

Uses

2-Benzoylbenzoic Acid is a reagent that is used in the synthesis of BzATP Triethylammonium Salt, which is a selective P2X purinergic agonist. It is more potent than ATP at homodimeric P2X7 receptors.

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

• 713-36-0 2-benzyltoluene 
• 80764-39-2 2-(2-Benzoylphenyl)-4,4-dimethyl-2-oxazoline 
• 88-65-3 2-bromobenzoic-acid 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 604-61-5 ethyl 2-benzoylbenzoate 
• 64-19-7 acetic acid 
• 861050-70-6 acetic acid-(2-methyl-3,4-diphenyl-[1]naphthyl ester) 
• 859774-26-8 5-ethyl-5-methyl-2,2-diphenyl-hept-3-ynoic acid 
• 102664-93-7 acetic acid-(3,4-diphenyl-[1]naphthyl ester) 
• 157133-64-7 2-benzyl-3-phenyl-1H-indene 
• 198068-07-4 3-methyl-1,2-diphenyl-1,2-dihydro-naphthalene-1,4-diol 
• 7664-93-9 sulfuric acid 
• 4746-79-6 1-(2'-benzoylphenyl)-2-phenylethane-1,2-dione 

Downstream Products

• 84-65-1 9,10-phenanthrenequinone 
• 857620-25-8 (2-benzoyl-benzoic acid )-acetic acid-anhydride 
• 95025-68-6 3-(2,4-dimethyl-phenyl)-3-phenyl-3H-isobenzofuran-1-one 
• 118-74-1 hexachlorobenzene 
• 632-58-6 tetrachlorophthalic acid 
• 861526-53-6 1,2,3,4,5,6,7-heptachloro-anthraquinone 
• 60456-75-9 1,1'-diphenyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione 
• 119-61-9 benzophenone 
• 613-31-0 9,10-dihydroanthracene 
• 120-12-7 anthracene 
• 612-35-1 2-Benzylbenzoic acid 
• 84-50-4 Anthraquinone-2,6-disulfonic acid 
• 3000-04-2 6-phenyl-3,4-dihydro-2H-benzo[f][1,4]diazocin-1-one 
• 13093-22-6 2-chloro-3-phenylindenone 

Relevant articles and documents

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.

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.].