3-Acetylbenzophenone

Base Information

• Chemical Name: 3-Acetylbenzophenone
• CAS No.: 66067-44-5
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: 2914500000
• UNII: 3DQM4A09S7
• DSSTox Substance ID: DTXSID80216268
• Nikkaji Number: J2.996.132H
• Wikidata: Q27257081
• Mol file: 66067-44-5.mol

Synonyms:1-(3-Benzoylphenyl)ethanone;3-Acetylbenzophenone;3-Benzoylacetophenone;m-Benzoylacetophenone;

Chemical Property of 3-Acetylbenzophenone

Chemical Property:

• Vapor Pressure: 3.73E-06mmHg at 25°C
• Refractive Index: 1.578
• Boiling Point: 385.7 °C at 760 mmHg
• Flash Point: 144.6 °C
• PSA: 34.14000
• Density: 1.126g/cm³
• LogP: 3.12020
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 289

Purity/Quality:

99% ^*data from raw suppliers

3-Acetylbenzophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC(=CC=C1)C(=O)C2=CC=CC=C2
• Uses: 3-Acetylbenzophenone (Ketoprofen EP Impurity A) is a Ketoprofen intermediate. Ketoprofen USP Related Compound D.

Technology Process of 3-Acetylbenzophenone

There total 26 articles about 3-Acetylbenzophenone 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: 97.0%

tert-butyl benzoyl(tert-butoxycarbonyl)carbamate (135364-97-5) + 3-acetylphenylboronic acid → (3-acetylphenyl)(phenyl)methanone (66067-44-5)

Guidance literature:

With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); potassium carbonate; In tetrahydrofuran; water; at 23 ℃; for 15h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b03191

Reference yield: 91.0%

benzoic acid phenyl ester (93-99-2) + 3-acetylphenylboronic acid → (3-acetylphenyl)(phenyl)methanone (66067-44-5)

Guidance literature:

With potassium phosphate; (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); water; In tetrahydrofuran; at 90 ℃; for 2h; Inert atmosphere; Sealed tube; Schlenk technique;

DOI:10.1021/acs.6bl2329

Reference yield: 91.0%

1-benzoylpyrrolidine-2,5-dione (6343-27-7) + 3-acetylphenylboronic acid → (3-acetylphenyl)(phenyl)methanone (66067-44-5)

Guidance literature:

With palladium diacetate; sodium carbonate; tricyclohexylphosphine tetrafluoroborate; In 1,4-dioxane; at 120 ℃; for 15h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c7ob02269g

upstream raw materials:

ketoprofen

(+)-α-(3-benzylphenyl)propionic acid

3-acetoxybenzoic acid

phenylboronic acid

Downstream raw materials:

[3-(hydroxymethyl)phenyl](phenyl)methanone

3-acetylbenzoic acid

3-benzoylbenzoic acid

ketoprofen

Refernces

• 1、 Faraggi, Tomer M.,Li, Wei,MacMillan, David W. C.. "Decarboxylative Oxygenation via Photoredox Catalysis". . p. 410 - 415. Retrieved 2019/12/24.
• 2、 Zhang, Yuqi,Wang, Zijia,Tang, Zhao,Luo, Zhongfeng,Wu, Hongxiang,Liu, Tingting,Zhu, Yulin,Zeng, Zhuo. "Water Phase, Room Temperature, Ligand-Free Suzuki–Miyaura Cross-Coupling: A Green Gateway to Aryl Ketones by C–N Bond Cleavage". . p. 1620 - 1628. Retrieved 2020/03/04.