2-Fluoro-6-trifluoromethylbenzaldehyde
[CAS# 60611-24-7]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 2-Fluoro-6-trifluoromethylbenzaldehyde
• Synonyms: a,a,a,6-Tetrafluoro-o-tolualdehyde
• Molecular Formula: C₈H₄F₄O
• Molecular Weight: 192.11
• CAS Registry Number: 60611-24-7
• EC Number: 625-623-0
• SMILES: C1=CC(=C(C(=C1)F)C=O)C(F)(F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.432 g/mL (Expl.)
• Index of Refraction: 1.459, Calc.^*
• Boiling Point: 189.4±40.0 °C (760 mmHg), Calc.^*, 156 °C (Expl.)
• Flash Point: 69.7±21.5 °C, Calc.^*, 82 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Fluoro-6-trifluoromethylbenzaldehyde is an aromatic aldehyde compound with the molecular formula C7H4F4O. It consists of a benzene ring substituted with a fluoro group at the 2-position, a trifluoromethyl group at the 6-position, and an aldehyde group at the 1-position. This compound is a member of the family of halogenated aromatic aldehydes and is known for its unique combination of functional groups, which confer particular reactivity and chemical properties.

The discovery and synthesis of 2-fluoro-6-trifluoromethylbenzaldehyde can be traced to studies on halogenated aromatic aldehydes, which have garnered attention in both synthetic organic chemistry and material science. The presence of the fluoro and trifluoromethyl substituents makes this compound especially useful in various synthetic reactions due to the electron-withdrawing effects of these groups. The trifluoromethyl group in particular is known to significantly impact the reactivity of aromatic compounds, often making them more resistant to oxidation or reduction.

2-Fluoro-6-trifluoromethylbenzaldehyde has applications in the synthesis of more complex organic molecules, particularly in the pharmaceutical and agrochemical industries. The compound's aldehyde group is highly reactive and can participate in nucleophilic addition reactions, such as those involving imines, hydrazones, and other derivatives, which makes it useful in the formation of key intermediates for the synthesis of biologically active molecules.

In pharmaceutical chemistry, 2-fluoro-6-trifluoromethylbenzaldehyde serves as an important building block for the creation of drug candidates. The fluoro and trifluoromethyl groups on the aromatic ring are known to influence the lipophilicity, stability, and biological activity of the compounds into which they are incorporated. These modifications can enhance the pharmacokinetic properties of potential therapeutic agents, making them more effective in reaching their target sites in the body.

The compound is also of interest in materials science due to the stability conferred by the trifluoromethyl group, which makes the compound resistant to various environmental conditions, such as oxidation and high temperatures. This stability is important for the development of materials used in electronics, coatings, and other specialized applications.

2-Fluoro-6-trifluoromethylbenzaldehyde has also been used as a precursor in the synthesis of other halogenated aromatic compounds, which find use in agrochemicals, such as pesticides and herbicides. Its unique electronic properties, imparted by the trifluoromethyl and fluoro groups, make it an effective intermediate for the development of new agrochemical agents with improved performance and selectivity.

Overall, 2-fluoro-6-trifluoromethylbenzaldehyde is an important compound in organic synthesis, with well-established applications in the pharmaceutical and agrochemical industries, as well as in materials science. Its combination of functional groups allows for selective chemical reactions, making it a valuable building block for the preparation of more complex molecules with desired properties.

References

Rayner, C.M. and Graham, M.A. (2001) ‘Perkin Condensation’, Science of Synthesis, 10, p. 159. Available at: https://science-of-synthesis.thieme.com/app/text/?id=SD-010-00209

Costa, L.D., Guieu, S., Faustino, M.A.F. and Tomé, A.C. (2022) ‘Straightforward synthesis of thiazolo[5,4-c]isoquinolines from dithiooxamide and 2-halobenzaldehydes’, New Journal of Chemistry, 46, p. 3615.
DOI: 10.1039/D1NJ05536D

Chevallier, F. and Mongin, F. (2008) ‘Functionalization of diazines and benzo derivatives through deprotonated intermediates’, Chemical Society Reviews, 37, p. 609.
DOI: 10.1039/B709416G