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232017

Sigma-Aldrich

Tetrachloro-1,4-benzoquinone

99%

Synonym(s):

2,3,5,6-Tetrachloro-1,4-benzoquinone, p-Chloranil, Chloranil

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About This Item

Linear Formula:
C6Cl4(=O)2
CAS Number:
118-75-2
Molecular Weight:
245.88
Beilstein:
393006
EC Number:
204-274-4
MDL number:
MFCD00001594
UNSPSC Code:
12162002
PubChem Substance ID:
24853870
NACRES:
NA.23

Assay

99%

form

solid

mp

289 °C (dec.) (lit.)

SMILES string

ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O

InChI

1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11

InChI key

UGNWTBMOAKPKBL-UHFFFAOYSA-N

Gene Information

human ... ACHE(43) , BCHE(590) , CES1(1066)

General description

Tetrachloro-1,4-benzoquinone (TCBQ) is a quinone compound with four chloride groups. The catalytic activity of quinone groups (benzoquinone) can be controlled by the chloride groups with large electronegativity.

Application

Synthesis of dibenzofurans via oxidative cyclization.
TCBQ can form a nanocomposite with multi-walled carbon nanotubes (MWCNTs) on a graphite electrode for nicotinamide adenine dinucleotide (NADH) oxidation. It can also provide pseudocapacitance and can be used as an electrode material for the development of supercapacitors. It may be used as an organic cathode and act as a redox mediator for the fabrication of lithium ion batteries.
Undergoes photoinduced cycloaddition reactions with stilbene derivatives and α,β-unsaturated carbonyl compounds. Fluorescence quencher.

Signal Word

Danger

Hazard Statements

H315,H317,H318,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An Insoluble Benzoquinone-Based Organic Cathode for Use in Rechargeable Lithium-Ion Batteries.
Luo Z, et al.
Angewandte Chemie (International ed. in English), 56(41), 12561-12565 (2017)
Tetsuya Takeya et al.
Organic letters, 9(15), 2807-2810 (2007-06-22)
A novel oxidative cyclization of quinone-arenols 5 leading to products 6 with a dibenzofuran-1,4-dione structure, which forms the core of several natural products, has been developed and applied to the synthesis of violet-quinone (4).
Journal of the Chemical Society. Perkin Transactions 1, 571-571 (1994)
J. Prakt. Chem./Chem.-Ztg., 335, 515-515 (1993)
Electrocatalytic activity of 2, 3, 5, 6-tetrachloro-1, 4-benzoquinone/multi-walled carbon nanotubes immobilized on edge plane pyrolytic graphite electrode for NADH oxidation.
Silva L, et al.
Electrochimica Acta, 53(14), 4706-4714 (2008)
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