4-Trifluoromethylbenzaldehyde

4-Trifluoromethylbenzaldehyde

Names
Other names α,α,α-trifluoro-4-tolualdehyde
Identifiers
CAS Number	455-19-6  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:156309
ChEMBL	ChEMBL4473405
ChemSpider	61311
EC Number	207-240-7
PubChem CID	67996
InChI InChI=1S/C8H5F3O/c9-8(10,11)7-3-1-6(5-12)2-4-7/h1-5H Key: BEOBZEOPTQQELP-UHFFFAOYSA-N
SMILES C1=CC(=CC=C1C=O)C(F)(F)F
Properties
Chemical formula	C8H5F3O
Molar mass	174.122 g·mol−1
Appearance	colorless oil
Density	1.275
Melting point	1–2 °C (34–36 °F; 274–275 K)
Boiling point	64 °C (147 °F; 337 K) 12 torr
Refractive index (nD)	1.463
Hazards
GHS labelling: [1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Trifluoromethylbenzaldehyde is the organofluorine compound with the formula CF₃C₆H₄CHO. 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. ^[2] Complementarily, it can be produced by trifluoromethylation of 4-formylphenylboronic acid. ^[3]

It readily condenses with amines to give imines. ^[4] It has been used in the synthesis of pharmaceuticals, such as Lanperisone. ^[5]

References

1. "4-(Trifluoromethyl)benzaldehyde". pubchem.ncbi.nlm.nih.gov.
2. Mai, Shaoyu; Li, Wendong; Li, Xue; Zhao, Yingwei; Song, Qiuling (2019). "Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides". Nature Communications. 10 (1): 5709. Bibcode:2019NatCo..10.5709M. doi:10.1038/s41467-019-13701-5. PMC   6911099 . PMID   31836718.
3. Ye, Yingda; Sanford, Melanie S. (2012). "Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF₃I". Journal of the American Chemical Society. 134 (22): 9034–9037. Bibcode:2012JAChS.134.9034Y. doi:10.1021/ja301553c. PMC   3415565 . PMID   22624669.
4. Habibi, Mohammad Hossein; Montazerozohori, Morteza; Lalegani, Arash; Harrington, Ross W.; Clegg, William (2006). "Synthesis, structural and spectroscopic properties of a new Schiff base ligand N,N′-bis(trifluoromethylbenzylidene)ethylenediamine". Journal of Fluorine Chemistry. 127 (6): 769–773. Bibcode:2006JFluC.127..769H. doi:10.1016/j.jfluchem.2006.02.014.
5. Shiozawa, A; Narita, K; Izumi, G; Kurashige, S; Sakitama, K; Ishikawa, M (January 1995). "Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants". European Journal of Medicinal Chemistry. 30 (1): 85–94. doi:10.1016/0223-5234(96)88213-4.