232017

Tetrachloro-1,4-benzoquinone

99%

• Synonym(s): 2,3,5,6-Tetrachloro-1,4-benzoquinone, p-Chloranil, Chloranil
• Linear Formula: C₆Cl₄(=O)₂
• CAS Number: 118-75-2
• Molecular Weight: 245.88
• Beilstein/REAXYS Number: 393006
• EC Number: 204-274-4
• MDL number: MFCD00001594
• UNSPSC Code: 12162002
• PubChem Substance ID: 24853870
• NACRES: NA.23

Properties

• Quality Level: 200
• 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)

Description

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.

Safety Information

• pictograms: GHS05,GHS07,GHS09
• signalword: Danger
• hcodes: H315,H317,H318,H410
• pcodes: P261 - P264 - P273 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves