Trifluorotoluene is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula of C₆H₅CF₃. This colorless

fluorocarbon Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are ...

is used as a specialty

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

and an intermediate in the production of pesticides and pharmaceuticals.Banks, R.E. Organofluorine Chemicals and their Industrial Applications, Ellis Horwood LTD, Chichester, 1979.

Synthesis

For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst: :PhX + CF₃I → PhCF₃ (where X = I, Br) Industrial production is done by reacting benzotrichloride with

hydrogen fluoride Hydrogen fluoride (fluorane) is an Inorganic chemistry, inorganic compound with chemical formula . It is a very poisonous, colorless gas or liquid that dissolves in water to yield hydrofluoric acid. It is the principal industrial source of fluori ...

in a pressurized reactor.Siegemund, Günter "Aromatic Compounds with Fluorinated Side-Chains" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH. . :PhCCl₃ + 3 HF → PhCF₃ + 3 HCl

Uses

Trifluorotoluene has a variety of niche uses.

Low toxicity alternative to dichloromethane

According to Ogawa and Curran, trifluorotoluene is similar to dichloromethane in standard acylation, tosylation, and silylation reactions. The

dielectric constant The relative permittivity (in older texts, dielectric constant) is the permittivity of a material expressed as a ratio with the electric permittivity of a vacuum. A dielectric is an insulating material, and the dielectric constant of an insul ...

s for dichloromethane and trifluorotoluene are 9.04 and 9.18, respectively, indicating similar solvating properties. Dipole moments compare less favorably: 1.89 and 2.86 D for dichloromethane and trifluorotoluene, respectively. Replacing dichloromethane is advantageous when conditions require higher boiling solvents, since trifluorotoluene boils at 103 °C it has a higher boiling point than dichloromethane, which has a boiling point of ~40 °C. As a solvent, trifluorotoluene is useful in mild Lewis-acid catalyzed reactions, such as the Friedel-Crafts preparations. The most common catalyst, aluminium trichloride reacts with trifluorotoluene at room temperature; however,

zinc chloride Zinc chloride is an Inorganic chemistry, inorganic chemical compound with the chemical formula, formula ZnCl2·''n''H2O, with ''n'' ranging from 0 to 4.5, forming water of hydration, hydrates. Zinc chloride, anhydrous and its hydrates, are colo ...

does not.

Synthetic intermediate

A second and perhaps more valuable use of trifluorotoluene is as a synthetic intermediate. A derivative of trifluorotoluene, 3-aminobenzotrifluoride, is the precursor to the herbicide fluometuron. It is synthesized via nitration followed by reduction to meta-H₂NC₆H₄CF₃. This

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

is then converted to the urea. Flumetramide (6- -(trifluoromethyl)phenylorpholin-3-one), a

skeletal muscle Skeletal muscle (commonly referred to as muscle) is one of the three types of vertebrate muscle tissue, the others being cardiac muscle and smooth muscle. They are part of the somatic nervous system, voluntary muscular system and typically are a ...

relaxant, is also prepared from trifluorotoluene.

Analytics

Trifluorotoluene appears in ¹⁹F NMR as a singlet at -63.2 ppm.

References

{{fluorine compounds Trifluoromethyl compounds Phenyl compounds Halogenated solvents Aromatic solvents