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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:
527-21-9
Molecular Weight:
180.06
NACRES:
NA.22
PubChem Substance ID:
24846640
UNSPSC Code:
12352100
EC Number:
208-411-9
MDL number:
MFCD00001592
Assay:
97%
Form:
solid
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Quality Level

100

assay

97%

form

solid

mp

183-186 °C (subl.) (lit.)

functional group

fluoro, ketone

SMILES string

FC1=C(F)C(=O)C(F)=C(F)C1=O

InChI

1S/C6F4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11

InChI key

JKLYZOGJWVAIQS-UHFFFAOYSA-N

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW2605
MKCW1598
MKCW6945
MKCR1843
MKCP0811

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Tetrafluoro-p-benzoquinone
Essers M and Haufe G
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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), 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
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Global Trade Item Number

SKUGTIN
104353-5G04061831809688
104353-1G04061838671721