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104353

Sigma-Aldrich

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
EC Number:
208-411-9
MDL number:
MFCD00001592
UNSPSC Code:
12352100
PubChem Substance ID:
24846640
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

mp

183-186 °C (subl.) (lit.)

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_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
A Facile and Convenient Synthesis of (?)-Dasycarpidone
Uludag N
Chemistry of Natural Compounds, 56(1), 105-108 (2020)
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)
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)
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