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/REAXYS Number:
393006
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

assay

99%

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

hazcat

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

storage_class_code

11 - Combustible Solids

WGK Germany

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

Certificate of Origin

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)
J. Prakt. Chem./Chem.-Ztg., 335, 515-515 (1993)
Synthesis of a polyacrylonitrile/tetrachloro-1, 4-benzoquinone gel polymer electrolyte for high-performance Li-air batteries.
Bok K, et al.
Journal of Membrane Science (2018)
Journal of the Chemical Society. Perkin Transactions 1, 571-571 (1994)
A benzoquinone-based cathode for Li-organic batteries.
Wei W, et al.
Materials Letters, 213(41), 126-130 (2018)

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