Trifluorotoluene

In today's world, Trifluorotoluene has become increasingly relevant in different areas of society. From its impact on the economy to its influence on everyday life, Trifluorotoluene has become a topic of constant interest and debate. Its importance lies in its ability to impact the way people, companies and institutions address different challenges and opportunities. In this article we will explore the various aspects related to Trifluorotoluene, from its origin and evolution to its potential consequences and benefits. Through detailed analysis, we will try to understand how Trifluorotoluene is shaping the world today and how it can influence the future.

Trifluorotoluene
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 Edit this at Wikidata
EC Number
  • 202-635-0
UNII
  • InChI=1S/C7H5F3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H
    Key: GETTZEONDQJALK-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(F)(F)F
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
1.41486 (13 °C)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
3
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 , 100 kPa).
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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]

Synthesis

For small-scale laboratory preparations, trifluorotoluene is synthesized by coupling an aromatic halide and trifluoromethyl iodide in the presence of a copper catalyst:[2]

PhX + CF3I → PhCF3 (where X = I, Br)

Industrial production is done by reacting benzotrichloride with hydrogen fluoride in a pressurized reactor.[3]

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.[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.

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.[3] It is synthesized via nitration followed by reduction to meta-H2NC6H4CF3. This aniline is then converted to the urea.

Flumetramide (6-morpholin-3-one), a skeletal muscle relaxant, is also prepared from trifluorotoluene.[1]

Analytics

Trifluorotoluene appears in 19F NMR as a singlet at -63.2 ppm.[5]

References

  1. ^ a b Banks, R.E. Organofluorine Chemicals and their Industrial Applications, Ellis Horwood LTD, Chichester, 1979.
  2. ^ Ogawa, Akiya; Tsuchii, Kaname "α,α,α-Trifluorotoluene" in Encyclopedia of Reagents for Organic Synthesis 2005, John Wiley and Sons. doi:10.1002/047084289X.rn00653
  3. ^ a b Siegemund, Günter "Aromatic Compounds with Fluorinated Side-Chains" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH. doi:10.1002/14356007.a11_349.
  4. ^ Ogawa, Akiya; Curran, Dennis P. (1997). "Benzotrifluoride: A Useful Alternative Solvent for Organic Reactions Currently Conducted in Dichloromethane and Related Solvents". Journal of Organic Chemistry. 62 (3): 450–451. doi:10.1021/jo9620324. PMID 11671431.
  5. ^ Denmark, Scott E.; Smith, Russell C. (3 February 2010). "Mechanistic Duality in Palladium-Catalyzed Cross-Coupling Reactions of Aryldimethylsilanolates. Intermediacy of an 8-Si-4 Arylpalladium(II) Silanolate (Supplementary Material, referenced as PhCF3)". Journal of the American Chemical Society. 132 (4): 1243–1245. doi:10.1021/ja907049y. PMC 2812642. PMID 20058920.