Benzotrifluoride

Trifluorotoluene

Names
Other names Benzotrifluoride (BTF) α,α,α-Trifluorotoluene CF3Ph PhCF3
Identifiers
CAS Number	98-08-8 Y
3D model (JSmol)	Interactive image
ChemSpider	7090
ECHA InfoCard	100.002.396
EC Number	202-635-0
PubChem CID	7368
InChI InChI=1S/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H Key: GETTZEONDQJALK-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C(F)(F)F
Properties
Chemical formula	C6H5CF3
Molar mass	146.11 g/mol
Appearance	colorless liquid
Odor	aromatic
Density	1.19 g/mL at 20 °C
Melting point	−29.05 °C (−20.29 °F; 244.10 K)
Boiling point	103.46 °C (218.23 °F; 376.61 K)
Solubility in water	<0.1 g/100 mL at 21 ºC
Solubility	soluble in ether, benzene, ethanol, acetone miscible in n-heptane, CCl4
Refractive index (nD)	1.41486 (13 °C)
Hazards
NFPA 704	3 0 0
Flash point	12 °C (54 °F; 285 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Trifluorotoluene is an organic compound with the formula of C₆H₅CF₃. This colorless fluorocarbon is used as a specialty solvent in organic synthesis and an intermediate in the production of pesticides and pharmaceuticals.

For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst:

Industrial production is done via reacting benzotrichloride with hydrogen fluoride in a pressurized reactor.

Trifluorotoluene has a variety of niche uses.

According to Ogawa and Curran, trifluorotoluene is similar to dichloromethane in standard acylation, tosylation, and silylation reactions. The dielectric constants 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 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 does not.

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 is then converted to the urea.