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104353

Sigma-Aldrich

Tetrafluoro-1,4-benzoquinone

97%

Sinónimos:

2,3,5,6-Tetrafluoroquinone, Fluoranil, Tetrafluorobenzoquinone

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About This Item

Fórmula lineal:
C6F4(=O)2
Número de CAS:
527-21-9
Peso molecular:
180.06
EC Number:
208-411-9
MDL number:
MFCD00001592
UNSPSC Code:
12352100
PubChem Substance ID:
24846640
NACRES:
NA.22

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

428566

2,6-Dimethoxy-1,4-benzoquinone

7,7,8,8-Tetracyanoquinodimethane 98%

Sigma-Aldrich

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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)
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
Ken Okamoto et al.
Journal of the American Chemical Society, 125(41), 12416-12417 (2003-10-09)
Self-promoted electron transfer from a cobalt(II) porphyrin [Co(II)OEP] to p-fluoranil (F4Q) occurs, exhibiting a second-order dependence of the electron-transfer rate with respect to the F4Q concentration due to the formation of a strong complex between the dimer radical anion [(F4Q)2*-]
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)
Complexation Behavior of Binaphthol/Tetrafluoro-1, 4-benzoquinone Charge-Transfer Complex.
Imai Y, et al.
Crystal Growth & Design, 9(5), 2393-2397 (2009)
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