Pentafluoromethylbenzene

Last updated
Pentafluoromethylbenzene
Pentafluorotoluene.svg
Names
Preferred IUPAC name
1,2,3,4,5-pentafluoro-6-methylbenzene
Other names
2,3,4,5,6-Pentafluorotoluene, Pentafluorotoluene, PFT
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.121 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-233-7
PubChem CID
UNII
  • InChI=1S/C7H3F5/c1-2-3(8)5(10)7(12)6(11)4(2)9/h1H3
    Key: SXPRVMIZFRCAGC-UHFFFAOYSA-N
  • FC=1C(F)=C(F)C(=C(F)C1F)C
Properties
C7H3F5
Molar mass 182.093 g·mol−1
AppearanceColorless liquid
Density 1.439 g/mL at 25 °C (lit.)
Melting point −29.8 °C (−21.6 °F; 243.3 K)
Boiling point 90–120 °C (194–248 °F; 363–393 K)
Poorly soluble
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H302+H312+H332, H315, H319, H335
Flash point 34 °C (93 °F; 307 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentafluoromethylbenzene is a synthetic organofluoride compound with the molecular formula C6F5CH3. [1] [2]

Contents

Synthesis

The compound can be obtained by the Friedel–Crafts reaction of pentafluorobenzene with methyl chloride. [3]

Also, the compound can be prepared by reacting hexafluorobenzene with methyllithium. [4] [5]

Physical properties

Pentafluoromethylbenzene is a colorless, volatile liquid with a distinctive sweet smell. [5] It is known for its high reactivity, low toxicity, and limited solubility. Additionally, it has the ability to form complexes with metals such as iron and copper. [6]

Chemical properties

The presence of electron-withdrawing fluorine atoms on its aromatic ring significantly enhances the compound reactivity. [6]

Under the influence of light, pentafluoromethylbenzene reacts with bromine to form pentafluorobenzyl bromide. [7]

Uses

This halogenated aromatic hydrocarbon is widely utilized in organic synthesis and analytical chemistry due to its unique characteristics. In scientific studies, the compound is frequently employed to synthesize a variety of organic compounds, including amides, ketones, and carboxylic acids. [6]

See also

References

  1. ↑ Lide, David R. (29 June 2004). CRC Handbook of Chemistry and Physics, 85th Edition. CRC Press. pp. 6–120. ISBN   978-0-8493-0485-9 . Retrieved 21 April 2025.
  2. ↑ Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S. Z.; Hu, L. Q.; Sung, K. S.; Desmarteau, D. D.; Yagupolskii, L. M. (1994). "Benzene, pentafluoromethyl-". NIST. p. 3047. doi:10.1021/ja00086a038 . Retrieved 21 April 2025.
  3. ↑ "2,3,4,5,6-Pentafluorotoluene". Sigma Aldrich . Retrieved 21 April 2025.
  4. ↑ Filler, R.; Kang, H. H. (1 January 1965). "Tetrafluorotyrosine: synthesis and properties" . Chemical Communications (24): 626–627. doi:10.1039/C19650000626. ISSN   0009-241X . Retrieved 21 April 2025.
  5. 1 2 Knunyants, I. L.; Yakobson, G. G. (6 December 2012). Syntheses of Fluoroorganic Compounds. Springer Science & Business Media. p. 129. ISBN   978-3-642-70207-5 . Retrieved 21 April 2025.
  6. 1 2 3 "2,3,4,5,6-Pentafluorotoluene | CAS 771-56-2 | SCBT - Santa Cruz Biotechnology". scbt.com . Retrieved 21 April 2025.
  7. ↑ Filler, Robert; Heffern, Edward W. (1 October 1967). "Bis(pentafluorophenyl)acetylene and 2,3,4,5,6-pentafluorodiphenylacetylene" . The Journal of Organic Chemistry . 32 (10): 3249–3251. doi:10.1021/jo01285a089. ISSN   0022-3263 . Retrieved 21 April 2025.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.