607-86-3

Basic information

• Product Name: Benzoic acid, 2-methyl-, anhydride
• Synonyms: Benzoic acid, 2-methyl-, anhydride;Bis(2-methylbenzenecarboxylic)anhydride;Bis(2-methylbenzoic acid)anhydride;(2-methylbenzoyl) 2-methylbenzoate;(2-methylphenyl)carbonyl 2-methylbenzoate;2-methylbenzoic acid (2-methylbenzoyl) ester;2-methylbenzoic anhydride
• CAS NO: 607-86-3
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Mol File: 607-86-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 37.0 to 41.0 °C
• Boiling Point: 221°C/11mmHg(lit.)
• Flash Point: 194°C
• Appearance: /
• Density: 1.1565 (rough estimate)
• Vapor Pressure: 6.94E-07mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• CAS DataBase Reference: Benzoic acid, 2-methyl-, anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-methyl-, anhydride(607-86-3)
• EPA Substance Registry System: Benzoic acid, 2-methyl-, anhydride(607-86-3)

Safety Data

• Hazardous Substances Data: 607-86-3(Hazardous Substances Data)

Usage

General Description

Benzoic acid, 2-methyl-, anhydride is a white crystalline compound with the chemical formula C9H8O3. It is primarily used as a chemical intermediate in the production of pharmaceuticals, fragrances, and flavorings. It is also commonly used as a reagent in organic synthesis and as a solvent in some chemical reactions. Benzoic acid, 2-methyl-, anhydride is known for its strong and irritating odor, and it should be handled with caution due to its potential to cause skin and eye irritation. Benzoic acid, 2-methyl-, anhydride is not considered to be highly toxic, but prolonged or repeated exposure may cause harm to health. It is important to handle and store this compound in a safe and appropriate manner.

InChI:InChI=1/C16H14O3/c1-11-7-3-5-9-13(11)15(17)19-16(18)14-10-6-4-8-12(14)2/h3-10H,1-2H3

Upstream product

• 201230-82-2 carbon monoxide 
• 108-88-3 toluene 
• 615-37-2 ortho-methylphenyl iodide 
• 89-95-2 2-methyl-benzyl alcohol 
• 529-20-4 2-methylphenyl aldehyde 
• 118-90-1 ortho-methylbenzoic acid 
• 2216-51-5 (-)-menthol 
• 95-46-5 2-methylphenyl bromide 
• 95-49-8 2-methylchlorobenzene 

Downstream Products

• 100728-74-3 N-(7⁽⁹⁾H-purin-6-yl)-o-toluamide 
• 933-88-0 ortho-toluoyl chloride 
• 41204-59-5 (4-methoxyphenyl)(2-methylphenyl)methanone 
• 6397-82-6 4'-methoxyhexanophenone 
• 50850-13-0 N-(2-methylbenzoyl)-2-nitroanilide 
• 60045-27-4 3-phenylpropionic acid 3-phenylpropyl ester 
• 141809-63-4 3-phenylpropyl 2-methylbenzoate 
• 577-16-2 2-Methylacetophenone 
• 127567-53-7 2-methylphenyl 2-naphthyl sulfide 
• 364-20-5 2-methylbenzoyl fluoride 
• 22682-29-7 dimethyl-2,3' benzophenone 
• 1182669-71-1 N-(2-methylbenzoyl)-8-aminoquinoline 

Relevant articles and documents

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.

PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.

Synthesis, molecular docking, and pharmacological evaluation of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives as selective COX-2 inhibitors and anti-inflammatory agents

A series of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives (3am) was synthesized and evaluated for their in vitro inhibitory activity against COX-1 and COX-2. The compounds with considerable in vitro activity (IC50 50 values in the range of 0.06–0.71 μM. The in vivo anti-inflammatory activity of these six compounds (3a, 3b, 3d, 3g, 3j, and 3k) was assessed by the carrageenan-induced rat paw edema method. Compounds 3d (84.09%), 3g (79.54%), and 3a (70.45%) demonstrated significant anti-inflammatory activity compared to the standard drug ibuprofen (65.90%) and were also found to be safer than ibuprofen, by ulcerogenic studies. A docking study was done using the crystal structure of human COX-2, to understand the binding mechanism of these inhibitors to the active site of COX-2.