Hexafluorobenzene

Hexafluorobenzene
Hexafluorobenzene
General
Systematic ; name	Hexafluorobenzene
Traditional names	Perfluorobenzene
Chem. formula	C 6 F 6
Thermal properties
T. melt.	5.29 ° C
T. bale.	80-81 ° C
Cr. point	242.9
Classification
Reg. CAS number
PubChem
Reg. EINECS number
Smiles
Inchi
RTECS
Chebi
ChemSpider

Hexafluorobenzene (perfluorobenzene) is a chemical compound of carbon and fluorine with the chemical formula C ₆ F ₆ , one of the representatives of aromatic perfluorinated organofluorine compounds .

Content

1 Physical and chemical properties
2 Getting
3 Application
4 Literature
5 See also

Physical and chemical properties

Hexafluorobenzene is a colorless liquid. Soluble in organic solvents, insoluble in water.

Hexafluorobenzene enters into a nucleophilic substitution reaction:

{\mathsf {C_{6}F_{6}{\xrightarrow[{150-200^{o}C}]{NH_{4}OH}}C_{6}F_{5}NH_{2}}}

{\ displaystyle {\ mathsf {C_ {6} F_ {6} {\ xrightarrow [{150-200 ^ {o} C}] {NH_ {4} OH}} C_ {6} F_ {5} NH_ {2} }}}

The reaction of hexafluorobenzene with electrophilic reagents leads to the destruction of the aromatic system. Thus, in the reaction with nitric acid, perfluoroquinone is formed.

In the reaction with active radicals, one or more fluorine atoms are replaced:

{\mathsf {C_{6}F_{6}+CF_{3}\cdot \rightarrow C_{6}F_{5}CF_{3}+F\cdot }}

{\ displaystyle {\ mathsf {C_ {6} F_ {6} + CF_ {3} \ cdot \ rightarrow C_ {6} F_ {5} CF_ {3} + F \ cdot}}}

Getting

Hexafluorobenzene is prepared in the following ways:

The reaction of alkali metal fluorides with hexachlorobenzene :

{\mathsf {C_{6}Cl_{6}+6NaF{\xrightarrow[{500-600^{o}C,\ 8-10MPa}]{}}C_{6}F_{6}+6NaCl}}

{\ displaystyle {\ mathsf {C_ {6} Cl_ {6} + 6NaF {\ xrightarrow [{500-600 ^ {o} C, \ 8-10MPa}] {}} C_ {6} F_ {6} + 6NaCl }}}

Fluorotribromomethane pyrolysis in the presence of a catalyst (Pt) at 630-640 ° C
Benzene fluoridation:

{\mathsf {C_{6}H_{6}{\xrightarrow[{}]{CoF_{3}}}C_{6}F_{12}{\xrightarrow[{500-600^{o}C}]{Fe}}C_{6}F_{6}}}

{\ displaystyle {\ mathsf {C_ {6} H_ {6} {\ xrightarrow [{}] {CoF_ {3}}} C_ {6} F_ {12} {\ xrightarrow [{500-600 ^ {o} C }] {Fe}} C_ {6} F_ {6}}}}

{\mathsf {C_{6}H_{6}{\xrightarrow[{}]{CoF_{3}}}C_{6}H_{3}F_{9}{\xrightarrow[{}]{KOH}}C_{6}F_{6}}}

{\ displaystyle {\ mathsf {C_ {6} H_ {6} {\ xrightarrow [{}] {CoF_ {3}}} C_ {6} H_ {3} F_ {9} {\ xrightarrow [{}] {KOH }} C_ {6} F_ {6}}}}

Application

Hexafluorobenzene is used for the synthesis of polyfluoroaromatic compounds and as a solvent for organic substances.

As well as tetramethylsilane , used as a standard for chemical shift in proton NMR spectroscopy , Hexafluorobenzene is used as a standard for relative measurement of chemical shift in NMR spectroscopy on fluorine-19 nuclei.

Literature

Knunyants I.L. et al. 1 A-Darzan // Chemical Encyclopedia. - M .: Soviet Encyclopedia, 1988 .-- 623 p. - 100,000 copies.
Rabinovich V. A., Khavin Z. Ya. “Brief chemical reference book”. - L .: Chemistry, 1977 .-- S. 139

Hexafluorobenzene

General
Systematic name	Hexafluorobenzene
Traditional names	Perfluorobenzene
Chem. formula	C ₆ F ₆
Thermal properties
T. melt.	5.29 ° C
T. bale.	80-81 ° C
Cr. point	242.9
Classification
Reg. CAS number
PubChem
Reg. EINECS number
Smiles
Inchi
RTECS
Chebi
ChemSpider