4-Trifluoromethylbenzaldehyde

4-Trifluoromethylbenzaldehyde
Names
	Other names α,α,α-trifluoro-4-tolualdehyde
Identifiers
CAS Number	455-19-6 ;
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:
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

^ "4-(Trifluoromethyl)benzaldehyde". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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. doi:10.1021/ja301553c. PMC 3415565. PMID 22624669.
^ 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.
^ 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.

[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. 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.

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