Tetrafluoro-1,4-benzoquinone

Name: Tetrafluoro-1,4-benzoquinone
Brand: ALDRICH
Price: 34.2 USD

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

Key Documents

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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

100

Related Categories

Chemical Building Blocks

Fluorinated Building Blocks

Halogenated Heterocycles

Organic Building Blocks

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1 of 4

This Item	100188	104361	H31204
Sigma-Aldrich 104353 Tetrafluoro-1,4-benzoquinone	Sigma-Aldrich 100188 2,3,5,6-Tetrafluorobenzenethiol	Sigma-Aldrich 104361 Tetrafluorohydroquinone	Sigma-Aldrich H31204 9-Hydroxyfluorene
assay 97%	assay 97%	assay 95%	assay 96%
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
form solid	form -	form -	form -
mp 183-186 °C (subl.) (lit.)	mp -	mp 172-174 °C (lit.)	mp 153-154 °C (lit.)
functional group fluoro	functional group fluoro	functional group -	functional group -

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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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Molecular mechanism for metal-independent production of hydroxyl radicals by hydrogen peroxide and halogenated quinones.

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

Self-promoted electron transfer from cobalt(II) porphyrin to p-fluoranil to produce a dimer radical anion-cobalt(III) porphyrin complex.

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*-]

Tetrafluoro-p-benzoquinone

Essers M and Haufe G

eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)

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)

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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Tetrafluoro-1,4-benzoquinone