Pentafluorobenzene

Last updated
Pentafluorobenzene
Pentafluorobenzene.svg
Names
Preferred IUPAC name
Pentafluorobenzene
Other names
Pentafluorobenzene, phenyl pentafluoride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.054 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-658-7
PubChem CID
UNII
  • InChI=1S/C6HF5/c7-2-1-3(8)5(10)6(11)4(2)9/h1H
    Key: WACNXHCZHTVBJM-UHFFFAOYSA-N
  • C1=C(C(=C(C(=C1F)F)F)F)F
Properties
C6HF5
Molar mass 168.066 g·mol−1
AppearanceColorless liquid
Density 1.511 g/cm3
Melting point −47.4 °C (−53.3 °F; 225.8 K)
Boiling point 85 °C (185 °F; 358 K)
Insoluble
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H315, H318, H335
Flash point 14 °C (57 °F; 287 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentafluorobenzene is a synthetic organofluoride compound with the molecular formula C
6HF
5. [1] The compound consists of a benzene ring substituted with five fluorine atoms. [2] The substance is a colorless liquid with a boiling point similar to that of benzene. [3] [4]

Contents

It is prepared by defluorination of highly fluorinated cyclohexanes over hot nickel or iron. [5] Another method involved dehydrofluorination of polyfluorinated cyclohexane using hot aqueous solution of potassium hydroxide. [6]

It has been observed as a degradation by-product of the incineration of polytetrafluoroethylene and of biosolids. [7]

Safety

According to its Safety Data Sheet (SDS), the chemical is highly flammable, and is harmful if swallowed. The SDS states its "toxicological properties have not been fully investigated". Combustion by-products include hydrogen fluoride. [8]

See also

References

  1. ↑ "Pentafluorobenzene". Sigma Aldrich . sigmaaldrich.com. Retrieved 8 June 2017.
  2. ↑ "Пентафторбензол" (in Russian). himreakt.ru. Retrieved 8 June 2017.
  3. ↑ "Pentafluorobenzene". NIST. webbook.nist.gov. Retrieved 8 June 2017.
  4. ↑ CRC Handbook of Chemistry and Physics , 90. Edition, CRC Press, Boca Raton, Florida, 2009, ISBN   978-1-4200-9084-0, Section 3, Physical Constants of Organic Compounds, p. 3-414.
  5. ↑ Gething, B.; Patrick, C. R.; Tatlow, J. C.; Banks, R. E.; Barbour, A. K.; Tipping, A. E. (1959). "Thermal Reactions of Highly Fluorinated Cyclo Hexadienes". Nature. 183 (4661): 586–587. Bibcode:1959Natur.183..586G. doi:10.1038/183586a0.
  6. ↑ Nield, E.; Stephens, R.; Tatlow, J. C. (1959). "31. Aromatic polyfluoro-compounds. Part I. The synthesis of aromatic polyfluoro-compounds from pentafluorobenzene". Journal of the Chemical Society (Resumed): 166. doi:10.1039/JR9590000166.
  7. ↑ Hakeem, Ibrahim Gbolahan; Halder, Pobitra; Patel, Savankumar; Selezneva, Ekaterina; Rathnayake, Nimesha; Marzbali, Mojtaba Hedayati; Veluswamy, Ganesh; Sharma, Abhishek; Kundu, Sazal; Surapaneni, Aravind; Megharaj, Mallavarapu; Batstone, Damien J.; Shah, Kalpit (August 2024). "Current understanding on the transformation and fate of per- and polyfluoroalkyl substances before, during, and after thermal treatment of biosolids". Chemical Engineering Journal. 493 152537. doi: 10.1016/j.cej.2024.152537 .
  8. ↑ "SAFETY DATA SHEET: Pentafluorobenzene". Thermo Fisher Scientific Chemicals, Inc. March 25, 2024. Retrieved 17 March 2025.
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