Pentafluorobenzene

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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
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 an organofluoride compound with the molecular formula C
6
HF
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] 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 KOH. [6]

See also

Related Research Articles

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<span class="mw-page-title-main">Naphthalene</span> Chemical compound

Naphthalene is an organic compound with formula C
10
H
8
. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs.

<span class="mw-page-title-main">Anthracene</span> Chemical compound

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Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products. Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.

Cyclohexa-1,3-diene (also known as Benzane) is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). A naturally occurring derivative of cyclohexa-1,3-diene is terpinene, a component of pine oil.

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<span class="mw-page-title-main">Silver(II) fluoride</span> Chemical compound

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<span class="mw-page-title-main">Cyclic compound</span> Molecule with a ring of bonded atoms

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<span class="mw-page-title-main">Antimony pentachloride</span> Chemical compound

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Perchloryl fluoride is a reactive gas with the chemical formula ClO
3
F
. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound consisting of a 6-sided ring

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The Birch reduction is an organic reaction that is used to convert arenes to 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent with an alkali metal and a proton source. Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane.

<span class="mw-page-title-main">Hexafluorobenzene</span> Chemical compound

Hexafluorobenzene, HFB, C
6
F
6
, or perfluorobenzene is an organofluorine compound. In this derivative of benzene, all hydrogen atoms have been replaced by fluorine atoms. The technical uses of the compound are limited, although it has some specialized uses in the laboratory owing to distinctive spectroscopic properties.

Pentafluorothiophenol is an organosulfur compound with the formula C6F5SH. It is a colorless volatile liquid. The compound is prepared by the reaction of sodium hydrosulfide and hexafluorobenzene. With a pKa of 2.68, it is one of the most acidic thiols. Its conjugate base has been used as a ligand in coordination chemistry

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7
H
7
I
. The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes.

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.