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Merck
CN

232017

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
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24853870
EC Number:
204-274-4
Beilstein/REAXYS Number:
393006
MDL number:
MFCD00001594

Key Documents

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Product Name

Tetrachloro-1,4-benzoquinone, 99%

InChI key

UGNWTBMOAKPKBL-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

99%

form

solid

mp

289 °C (dec.) (lit.)

Quality Level

200

Gene Information

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

Related Categories

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.

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.

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Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

农药列管产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCK7552
BCCD0305
BCCB8938
BCBV8858
BCBZ3538

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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).
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)
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)
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