H8706
Hexafluorobenzene
99%
Synonym(s):
Perfluorobenzene
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About This Item
Empirical Formula (Hill Notation):
C6F6
CAS Number:
Molecular Weight:
186.05
Beilstein/REAXYS Number:
1683438
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
99%
form
liquid
refractive index
n20/D 1.377 (lit.)
bp
80-82 °C (lit.)
mp
3.7-4.1 °C (lit.)
density
1.612 g/mL at 25 °C (lit.)
SMILES string
Fc1c(F)c(F)c(F)c(F)c1F
InChI
1S/C6F6/c7-1-2(8)4(10)6(12)5(11)3(1)9
InChI key
ZQBFAOFFOQMSGJ-UHFFFAOYSA-N
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Application
Hexafluorobenzene can react with:
It can be used:
- 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.
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
50.0 °F - closed cup
flash_point_c
10 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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A hexafluorobenzene promoted ring-closing metathesis to form tetrasubstituted olefins.
Rost D, et al.
Tetrahedron Letters, 49(41), 5968-5971 (2008)
A new synthesis of perfluoroaromatic Grignard reagents.
Respess W L, et al.
Journal of Organometallic Chemistry, 18(2), 263-274 (1969)
Synthesis of hexakis (aryloxy) benzenes: x-ray analysis of hexakis (phenyloxy) benzene and of the acetonitrile clathrate of hexakis (3, 5-dimethylphenyloxy) benzene
Gilmore C J, et al.
Tetrahedron Letters, 24(31), 3269-3272 (1983)
Synthesis of new ? 4-hexafluorobenzene complexes of ruthenium and osmium from atoms of the metals: crystal structure of [Ru (? 6-C 6 H 3 Me 3-1, 3, 5)(? 4-C 6 F 6)]
Martin A, et al.
Journal of the Chemical Society, (15), 2251-2255 (1994)
Rajesh K Raju et al.
Physical chemistry chemical physics : PCCP, 12(28), 7959-7967 (2010-06-03)
The effect of benzene fluorination on C-H...pi interactions is studied using a number of computational methods applied to a range of intermolecular complexes. High level wavefunction methods (CCSD(T)) predict a slightly greater interaction energy for complexes of benzene with methane
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