Trifluorotoluene is an organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula of C₆H₅CF₃. This colorless fluorocarbon

Fluorocarbon

Fluorocarbons, sometimes referred to as perfluorocarbons or PFCs, are organofluorine compounds that contain only carbon and fluorine bonded together in strong carbon–fluorine bonds. Fluoroalkanes that contain only single bonds are more chemically and thermally stable than alkanes...

 is used as a specialty solvent

Solvent

A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

 in organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

 and an intermediate in the production of pesticides and pharmaceuticals.

Synthesis

For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide

Trifluoromethyl iodide

Trifluoroiodomethane, also referred to as trifluoromethyl iodide is a halomethane with the formula CF3I. It is an experimental alternative to Halon 1301 in unoccupied areas...

 in the presence of a copper catalyst:

ArX + CF₃I → Ar-CF₃ + CuXI (where X = I, Br, Cl)

For large scale preparations using batch or continuous processes, benzotrichloride

Benzotrichloride

Benzotrichloride, also known as trichlorotoluene is an organic compound with the formula C6H5CCl3. It is principally used as an intermediate in the preparation of other chemical products such as dyes.-Production and uses:...

 is treated with hydrogen fluoride

Hydrogen fluoride

Hydrogen fluoride is a chemical compound with the formula HF. This colorless gas is the principal industrial source of fluorine, often in the aqueous form as hydrofluoric acid, and thus is the precursor to many important compounds including pharmaceuticals and polymers . HF is widely used in the...

 under pressure.

C₆H₅CCl₃ + 3 HF → C₆H₅CF₃ + 3 HCl

Solvent alternative to dichloromethane

According to Ogawa and Curran, trifluorotoluene is similar to dichloromethane

Dichloromethane

Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

 in standard acylation

Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....

, tosylation, and silylation

Silylation

Silylation is the introduction of a substituted silyl group to a molecule.Nearly all functional groups which present a problem in gas chromatogaphic separation can be derivatized by silylation reagents...

 reactions. The dielectric constant

Dielectric constant

The relative permittivity of a material under given conditions reflects the extent to which it concentrates electrostatic lines of flux. In technical terms, it is the ratio of the amount of electrical energy stored in a material by an applied voltage, relative to that stored in a vacuum...

s for dichloromethane and trifluorotoluene are 9.04 and 9.18, respectively, indicative 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 62 °C higher than dichloromethane (b.p. 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

Zinc chloride is the name of chemical compound with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. ZnCl2 itself is hygroscopic and even deliquescent. Samples should therefore be protected from...

 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

Fluometuron

Fluometuron is an herbicide. In the United States it was approved for use on cotton and sugarcane crops in 1974, but since 1986 is only approved for use on cotton....

. It is synthesized via nitration

Nitration

Nitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...

 followed by reduction to meta-H₂NC₆H₄CF₃. This aniline

Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...

is then converted to the urea.

Flumetramide (6-[4-(trifluoromethyl)phenyl]morpholin-3-one), a skeletal muscle relaxant, is also prepared from trifluorotoluene.