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Names | |||
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Preferred IUPAC name
(Trifluoromethyl)benzene | |||
Other names
Benzotrifluoride (BTF)
α,α,α-Trifluorotoluene CF3Ph PhCF3 | |||
Identifiers | |||
3D model (
JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.002.396 | ||
EC Number |
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PubChem
CID
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UNII | |||
CompTox Dashboard (
EPA)
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Properties | |||
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) | ||
<0.1 g/100 mL at 21 °C | |||
Solubility | soluble in
ether,
benzene,
ethanol,
acetone miscible in n-heptane, CCl4 | ||
Refractive index (nD)
|
1.41486 (13 °C) | ||
Hazards | |||
NFPA 704 (fire diamond) | |||
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).
|
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. [1]
For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst: [2]
Industrial production is done by reacting benzotrichloride with hydrogen fluoride in a pressurized reactor. [3]
Trifluorotoluene has a variety of niche uses.
According to Ogawa and Curran, trifluorotoluene is similar to dichloromethane in standard acylation, tosylation, and silylation reactions. [4] 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 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 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. [3] It is synthesized via nitration followed by reduction to meta-H2NC6H4CF3. This aniline is then converted to the urea.
Flumetramide (6-[4-(trifluoromethyl)phenyl]morpholin-3-one), a skeletal muscle relaxant, is also prepared from trifluorotoluene. [1]
Trifluorotoluene appears in 19F NMR as a singlet at -63.2 ppm. [5]
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
(Trifluoromethyl)benzene | |||
Other names
Benzotrifluoride (BTF)
α,α,α-Trifluorotoluene CF3Ph PhCF3 | |||
Identifiers | |||
3D model (
JSmol)
|
|||
ChemSpider | |||
ECHA InfoCard | 100.002.396 | ||
EC Number |
| ||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
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) | ||
<0.1 g/100 mL at 21 °C | |||
Solubility | soluble in
ether,
benzene,
ethanol,
acetone miscible in n-heptane, CCl4 | ||
Refractive index (nD)
|
1.41486 (13 °C) | ||
Hazards | |||
NFPA 704 (fire diamond) | |||
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).
|
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. [1]
For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst: [2]
Industrial production is done by reacting benzotrichloride with hydrogen fluoride in a pressurized reactor. [3]
Trifluorotoluene has a variety of niche uses.
According to Ogawa and Curran, trifluorotoluene is similar to dichloromethane in standard acylation, tosylation, and silylation reactions. [4] 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 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 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. [3] It is synthesized via nitration followed by reduction to meta-H2NC6H4CF3. This aniline is then converted to the urea.
Flumetramide (6-[4-(trifluoromethyl)phenyl]morpholin-3-one), a skeletal muscle relaxant, is also prepared from trifluorotoluene. [1]
Trifluorotoluene appears in 19F NMR as a singlet at -63.2 ppm. [5]