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H8706

Sigma-Aldrich

Hexafluorobenzene

99%

Synonym(s):

Perfluorobenzene

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About This Item

Empirical Formula (Hill Notation):
C6F6
CAS Number:
392-56-3
Molecular Weight:
186.05
Beilstein:
1683438
EC Number:
206-876-2
MDL number:
MFCD00000288
UNSPSC Code:
12352100
PubChem Substance ID:
24895528
NACRES:
NA.22

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:
  • 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.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

50.0 °F - closed cup

Flash Point(C)

10 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
A new synthesis of perfluoroaromatic Grignard reagents.
Respess W L, et al.
Journal of Organometallic Chemistry, 18(2), 263-274 (1969)
A hexafluorobenzene promoted ring-closing metathesis to form tetrasubstituted olefins.
Rost D, et al.
Tetrahedron Letters, 49(41), 5968-5971 (2008)
Tobias Hahn et al.
Radiology, 265(3), 917-925 (2012-09-22)
To combine fluorine 19 ((19)F) magnetic resonance (MR) imaging and golden angle radial acquisition and to assess the feasibility of (19)F MR imaging golden angle-based tracking for catheter tracking applications and simultaneous three-dimensional (3D) intestinal tracking of ingested (19)F-labeled capsules
Jay C Amicangelo et al.
The journal of physical chemistry. A, 117(6), 1336-1350 (2012-10-27)
The lone pair-π interaction between H(2)O and C(6)F(6) was studied using matrix isolation infrared spectroscopy and quantum chemical calculations. Co-deposition of H(2)O with C(6)F(6) in a nitrogen matrix at 17 K followed by annealing to 30 K, results in the
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