2-Acetylbenzoic acid

Base Information

• Chemical Name: 2-Acetylbenzoic acid
• CAS No.: 577-56-0
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 29183000
• European Community (EC) Number: 209-413-2
• NSC Number: 407680
• DSSTox Substance ID: DTXSID00206404
• Nikkaji Number: J95.012B
• Wikidata: Q72434812
• ChEMBL ID: CHEMBL3629240
• Mol file: 577-56-0.mol

Synonyms:Benzoicacid, o-acetyl- (6CI,7CI,8CI);2-Acetophenonecarboxylic acid;2'-Carboxyacetophenone;NSC 407680;o-Acetophenonecarboxylic acid;o-Acetylbenzoic acid;o-Carboxyacetophenone;

Chemical Property of 2-Acetylbenzoic acid

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 115-117 °C(lit.)
• Refractive Index: 1.604
• Boiling Point: 319.093 °C at 760 mmHg
• PKA: pK1: 4.13 (25°C)
• Flash Point: 160.998 °C
• PSA: 54.37000
• Density: 1.23 g/cm³
• LogP: 1.58740
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Dichloromethane, Ethyl Acetate, Methanol (Slightly)
• Water Solubility.: Soluble in Dichloromethane and Ethyl Acetate. Slightly soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 198

Purity/Quality:

98% ^*data from raw suppliers

2-Acetylbenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC=CC=C1C(=O)O
• Uses: A common component of hair dyes. 2-Acetylbenzoic acid is used as a component of hair dyes. It is used as an intermediate for pharmaceutical, cosmetics, agrochemical and food industries.

Technology Process of 2-Acetylbenzoic acid

There total 54 articles about 2-Acetylbenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

trifluoromethanesulfonic acid 2-acetylphenyl ester (129849-05-4) → 2-acetyl-benzoic acid (577-56-0)

Guidance literature:

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; at 150 ℃; for 0.333333h; microwave irradiation;

DOI:10.1055/s-2006-926288

Reference yield: 91.0%

methyl 2-acetylbenzoate (1077-79-8) → 2-acetyl-benzoic acid (577-56-0)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; water; for 2h; Heating;

DOI:10.1016/S0040-4039(02)00990-5

Reference yield: 85.0%

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + trifluoromethanesulfonic acid 2-acetylphenyl ester (129849-05-4) → 2-acetyl-benzoic acid (577-56-0)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; water; at 20 ℃; for 16h; chemoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201600736

upstream raw materials:

pyridine

phthalic anhydride

malonic acid

3-methylidenephthalide

Downstream raw materials:

2-(2-methoxy-trans-cinnamoyl)-benzoic acid

N-(3-Methylenphthalidyl)-glycin

methyl 2-acetylbenzoate

2-(2-phenyl-thiazol-4-yl)-benzoic acid ethyl ester

Refernces

• 1、 Yang, Guoping,Li, Ke,Lin, Xiaoling,Li, Yijin,Cui, Chengxing,Li, Shixiong,Cheng, Yuanyuan,Liu, Yufeng. "Regio- and Stereoselective Synthesis of (Z)-3-Ylidenephthalides via H3PMo12O40-Catalyzed Cyclization of 2-Acylbenzoic Acids with Benzylic Alcohols". supporting information. p. 3017 - 3022. Retrieved 2021/09/13.
• 2、 Knaus, Tanja,Tseliou, Vasilis,Humphreys, Luke D.,Scrutton, Nigel S.,Mutti, Francesco G.. "A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids". supporting information. p. 3931 - 3943. Retrieved 2018/09/11.