104353
Tetrafluoro-1,4-benzoquinone
97%
Synonym(s):
2,3,5,6-Tetrafluoroquinone, Fluoranil, Tetrafluorobenzoquinone
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About This Item
Linear Formula:
C6F4(=O)2
CAS Number:
Molecular Weight:
180.06
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
208-411-9
MDL number:
Assay:
97%
Form:
solid
InChI key
JKLYZOGJWVAIQS-UHFFFAOYSA-N
InChI
1S/C6F4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
SMILES string
FC1=C(F)C(=O)C(F)=C(F)C1=O
assay
97%
form
solid
mp
183-186 °C (subl.) (lit.)
functional group
fluoro, ketone
Quality Level
General description
Tetrafluoro-1,4-benzoquinone is a fluorinated building block, commonly used as a precursor for fluoro derivatives.
Application
Tetrafluoro-1,4-benzoquinone (fluoranil) can be used to prepare:
- Symmetrical or unsymmetrical ethers by coupling of two alcohols via the oxidation-reduction condensation reaction.
- Azocino[4,3-b]indole scaffold, which is used as an inetermediate to prepare (±)-dasycarpidone.
- Chiral and racemic charge-transfer (CT) complexes with binaphthol.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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A Convenient Method for the Preparation of Symmetrical or Unsymmetrical Ethers by The Coupling of Two Alcohols via A New Type of Oxidation-reduction Condensation Using Tetrafluoro-1, 4-benzoquinone
Shintou T and Mukaiyama T
Chemistry Letters (Jpn), 32(11), 984-985 (2003)
Ben-Zhan Zhu et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(45), 17575-17578 (2007-10-31)
We have shown previously that hydroxyl radicals (HO*) can be produced by H2O2 and halogenated quinones, independent of transition metal ions; however, the underlying molecular mechanism is still unclear. In the present study, using the electron spin resonance secondary radical
Complexation Behavior of Binaphthol/Tetrafluoro-1, 4-benzoquinone Charge-Transfer Complex.
Imai Y, et al.
Crystal Growth & Design, 9(5), 2393-2397 (2009)
Generation and spectroscopic characterization of the 2, 3, 5, 6-tetramethoxy-1, 4-benzosemiquinone reactive intermediate.
Mattar SM, et al.
Chemical Physics Letters, 352(1), 39-47 (2002)
Tetrafluoro-p-benzoquinone
Essers M and Haufe G
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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