Hexafluorbenzol

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H225：Flüssigkeit und Dampf leicht entzündbar.

• Sicherheit

  P210：Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.

  P233：Behälter dicht verschlossen halten.

  P240：Behälter und zu befüllende Anlage erden.

  P241：Explosionsgeschützte [elektrische/Lüftungs-/ Beleuchtungs-/...] Geräte verwenden.

  P242：Nur funkenfreies Werkzeug verwenden.

  P243：Maßnahmen gegen elektrostatische Entladungen treffen.

hexafluorobenzene Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R11:Leichtentzündlich.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S16:Von Zündquellen fernhalten - Nicht rauchen.
  S33:Maßnahmen gegen elektrostatische Aufladungen treffen.
  S7/9:Behälter dicht geschlossen an einem gut gelüfteten Ort aufbewahren.
  S29:Nicht in die Kanalisation gelangen lassen.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

• Beschreibung

  Hexafluorobenzene, HFB, C6F6, or perfluorobenzene is an organic, aromatic 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 In this derivative of benzene all hydrogen atoms have been replaced by fluorine atoms.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 is recommended as a solvent in a number of photochemical reactions. In the laboratory hexafluorobenzene is used as standard in fluorine-19 NMR spectroscopy, solvent and standard in carbon-13 NMR, solvent in proton NMR, solvent when studying some parts in the infrared and solvent in ultraviolet–visible spectroscopy, as hexafluorobenzene itself hardly shows any absorbance in the UV region.

• Chemische Eigenschaften

  colourless liquid

• Verwenden

  Hexafluorobenzene can be used as a standard in ¹⁹Fluorine NMR (nuclear magnetic resonance) spectroscopy and also as a solvent in ¹³Carbon and ¹H NMR spectroscopy.

• Verwenden

  Hexafluorobenzene is used as a solvent in photochemical reactions. It is also used as a reference compound in fluorine-19 NMR, carbon-13 NMR. It is used as a solvent in proton NMR, IR spectrum and UV-spectra. It is used as anticorrosive, antifriction and anti-tumor agents. Further, it is used as a reference molecule to investigate tissue oxygenation in vivo studies. It forms series of 1:1 complexes with naphthalene, anthracene, phenanthrene, pyrene and triphenylene.

• Definition

  ChEBI: A member of the class of fluorobenzenes that is benzene in which all six hydrogen atom have been replaced by fluorine.

• Application

  Hexafluorobenzene can react with:
  Ethyl magnesium bromide in the presence of transition metal halides to form the corresponding perfluoroarylmagnesium compound that can undergo Grignard reactions.
  The sodium salt of the appropriate phenol in 1,3-dimethyl-2-imidazolidinone (DMEU) to form the corresponding hexakis(aryloxy)benzenes.
  It can be used:
  As a ligand to synthesize novel ruthenium(0) and osmium(0) hexafluorobenzene complexes.
  As a solvent and promoter for the ring-closing metathesis (RCM) to form tetrasubstituted olefins in the presence of a ruthenium-based catalyst.

• Reaktionen

  For example, hexafluorobenzene adds chlorine quite readily under rather mild conditions to give hexachlorohexafluorocyclohexane. The catalytic reduction of hexafluorobenzene with hydrogen to penta. and tetra-fluorobenzene at 300 °C, using a platinum catalyst, probably proceeds by a free-radical mechanism. Although the addition of chlorine to hexafluorobenzene is an example of a free-radical addition reaction, the reduction of hexafluorobenzene with hydrogen is classified as a freeradical substitution reaction.
  One of the earliest and, perhaps, most complicated reactions of hexafluorobenzene is one reported by Desirant. This interesting reaction, whic h is the only example of a high· temperature (above 300°C) reaction of hexafluorobenzene reported to date, involves the pyrolysis of the molecule in a platinum reactor at 850°C. Among the many products produced in this reaction , octafluorotoluene and decafluorobiphenyl were identified. This highly complex reaction probably could also be classified, in some respects, as a free-radical substitution reaction. There is also some less direct evidence that hightemperature reactions of hexafluorobe nzene do occur. In the synthesis of hexafluorobenzene by the pyrolysis of tribromofluoromethane, bromopentafluorobenzene is a signifi'cant by-product. Lesser amounts of higher brominated fluorocarbons are formed as well, along with copious quantities of bromine. This rather complex reaction is illustrated below.
  CFBr3--630-640℃-->C6F6+Br2+C6F5Br+C6F4Br2+etc.

• Allgemeine Beschreibung

  Hexafluorobenzene was repoted to be a sensitive ¹⁹F NMR indicator of tumor oxygenation. Rotational Raman spectra of hexafluorobenzenehas been studied under high resolution using a single mode argon laser as the exciting source. Hexafluorobenzene in the gas phase reacts spontaneously with lithium amalgam, to give a solid and intimate mixture of lithium fluoride and elemental polymeric carbon with a small amount of superstoichiometric lithium. Hexafluorobenzene forms series of 1:1 complexes with naphthalene, anthracene,phenanthrene, pyrene and triphenylene.

• Hazard

  Toxic by inhalation. Combustible.

• Synthese

  The direct synthesis of hexafluorobenzene from benzene and fluorine is not possible. The synthetic route proceeds via the reaction of alkali-fluorides with halogenated benzene:
  C6Cl6 + 6 KF → C6F6 + 6 KCl

• läuterung methode

  Main impurities are incompletely fluorinated benzenes. Purify it by standing in contact with oleum for 4hours at room temperature, repeating until the oleum does not become coloured. Wash it several times with water, then dry it with P2O5. Finally purify it by repeated fractional crystallisation. [Beilstein 5 III 523, 5 IV 640.]

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