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hexafluorobenzene

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CAS:392-56-3
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hexafluorobenzene manufacturers

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  • 2023-06-20
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hexafluorobenzene Basic information
Product Name:hexafluorobenzene
Synonyms:1,2,3,4,5,6-Hexafluorobenzene;benzene,hexafluoro-;CP 28;HEXAFLUOROBENZENE FOR SYNTHESIS;hexafluorobenzene radical cation;hexafluoro-benzen;HEXAFLUOROBENZENE, 99.5+%, NMR GRADE;HEXAFLUOROBENZENE, FOR NMR-SPECTROSCOPY
CAS:392-56-3
MF:C6F6
MW:186.05
EINECS:206-876-2
Product Categories:Fluorobenzene;Fluorous Chemistry;Fluorous Solvents;Synthetic Organic Chemistry;Aryl;C6;Halogenated Hydrocarbons;NMR - Solvents;NMR Solvents and Reagents;C6Stable Isotopes;Alphabetical Listings;G-HStable Isotopes;NMR;organofluorine compounds
Mol File:392-56-3.mol
hexafluorobenzene Structure
hexafluorobenzene Chemical Properties
Melting point 3.7-4.1 °C (lit.)
Boiling point 80-82 °C (lit.)
density 1.612 g/mL at 25 °C (lit.)
refractive index n20/D 1.377(lit.)
Fp 50 °F
storage temp. Sealed in dry,Room Temperature
form Liquid
color Clear colorless to slightly yellow
Specific Gravity1.612
Water Solubility Immiscible with water.
Merck 14,4686
BRN 1683438
Dielectric constant2.0499999999999998
Stability:Stable. Incompatible with strong oxidizing agents. May form complexes with transition metals which can explode when heated. Highly flammable.
CAS DataBase Reference392-56-3(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, hexafluoro-(392-56-3)
EPA Substance Registry SystemBenzene, hexafluoro- (392-56-3)
Safety Information
Hazard Codes F,Xi
Risk Statements 11-36/37/38
Safety Statements 16-33-7/9-29-26-37/39
RIDADR UN 1993 3/PG 2
WGK Germany 3
RTECS DA3050000
10
Hazard Note Highly Flammable
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29039990
Toxicityguinea pig,LCLo,inhalation,11800ppm/4H (11800ppm),BEHAVIORAL: ATAXIASENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYELUNGS, THORAX, OR RESPIRATION: OTHER CHANGES,National Technical Information Service. Vol. OTS0571186,
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
hexafluorobenzene Usage And Synthesis
DescriptionHexafluorobenzene, 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 In this derivative of benzene all hydrogen atoms have been replaced by fluorine atoms.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.
Chemical Propertiescolourless liquid
UsesHexafluorobenzene can be used as a standard in 19Fluorine NMR (nuclear magnetic resonance) spectroscopy and also as a solvent in 13Carbon and 1H NMR spectroscopy.
UsesHexafluorobenzene 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.
DefinitionChEBI: A member of the class of fluorobenzenes that is benzene in which all six hydrogen atom have been replaced by fluorine.
ApplicationHexafluorobenzene 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.
ReactionsFor 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.
General DescriptionHexafluorobenzene 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.
HazardToxic by inhalation. Combustible.
SynthesisThe 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
Purification MethodsMain 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.]
Tag:hexafluorobenzene(392-56-3) Related Product Information
Pentafluorobenzaldehyde Pentafluorobenzoyl chloride Bromopentafluorobenzene METHYL PENTAFLUOROBENZOATE Pentafluorophenol Pentafluorobenzene 1,3,5-Trifluorobenzene 1,2-Difluorobenzene Fluorobenzene 1,2,4,5-Tetrafluorobenzene 1,4-Difluorobenzene HYDROFLUORIC ACID 1,2,3-Trifluorobenzene 1,3-Difluorobenzene METHYL FLUORIDE hexafluorobenzene 1,2,3,5-Tetrafluorobenzene 1,2,4-Trifluorobenzene