4-Trifluoromethylbenzaldehyde Explained
4-Trifluoromethylbenzaldehyde is the organofluorine compound with the formula . Two other isomers are also known: 2-trifluoromethylbenzaldehyde and 3-trifluoromethylbenzaldehyde. These compounds are derivatives of benzaldehyde with trifluoromethyl substituents. The CF3 group enhances the electrophilicity of the formyl group and provides a label for analysis by fluorine-19 nuclear magnetic resonance spectroscopy.
Synthesis and reactions
It can be prepared by a Suzuki-Miyaura coupling from the 4-trifluoromethylphenylboronic acid.[1] Complementarily, it can be produced by trifluoromethylation of 4-formylphenylboronic acid.[2]
It readily condenses with amines to give imines.[3] It has been used in the synthesis of pharmaceuticals, such as Lanperisone.[4]
Notes and References
- 10.1038/s41467-019-13701-5 . Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides . 2019 . Mai . Shaoyu . Li . Wendong . Li . Xue . Zhao . Yingwei . Song . Qiuling . Nature Communications . 10 . 1 . 5709 . 31836718 . 6911099 . 2019NatCo..10.5709M .
- 10.1021/ja301553c . Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I . 2012 . Ye . Yingda . Sanford . Melanie S. . Journal of the American Chemical Society . 134 . 22 . 9034–9037 . 22624669 . 3415565 .
- 10.1016/j.jfluchem.2006.02.014 . Synthesis, structural and spectroscopic properties of a new Schiff base ligand N,N′-bis(trifluoromethylbenzylidene)ethylenediamine . 2006 . Habibi . Mohammad Hossein . Montazerozohori . Morteza . Lalegani . Arash . Harrington . Ross W. . Clegg . William . Journal of Fluorine Chemistry . 127 . 6 . 769–773 . 2006JFluC.127..769H .
- Shiozawa . A . Narita . K . Izumi . G . Kurashige . S . Sakitama . K . Ishikawa . M . Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants . European Journal of Medicinal Chemistry . January 1995 . 30 . 1 . 85–94 . 10.1016/0223-5234(96)88213-4.
