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232017

Sigma-Aldrich

Tetrachloro-1,4-benzoquinone

99%

Synonym(s):
p-Chloranil, 2,3,5,6-Tetrachloro-1,4-benzoquinone, Chloranil
Linear Formula:
C6Cl4(=O)2
CAS Number:
Molecular Weight:
245.88
Beilstein:
393006
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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

Related Categories

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

Undergoes photoinduced cycloaddition reactions with stilbene derivatives and α,β-unsaturated carbonyl compounds. Fluorescence quencher.
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.
Synthesis of dibenzofurans via oxidative cyclization.

Packaging

25, 100 g in poly bottle

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

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

Certificate of Analysis

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Certificate of Origin

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