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Sigma-Aldrich

2,6-Dichloro-1,4-benzoquinone

98%

Synonym(s):

2,6-Dichloro-2,5-cyclohexadiene-1,4-dione, 2,6-Dichloro-p-benzoquinone, 2,6-Dichlorobenzoquinone, 2,6-Dichloroquinone

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About This Item

Empirical Formula (Hill Notation):
C6H2Cl2O2
CAS Number:
697-91-6
Molecular Weight:
176.98
EC Number:
211-810-0
MDL number:
MFCD00037159
UNSPSC Code:
12352100
PubChem Substance ID:
24867060
NACRES:
NA.22

Assay

98%

mp

122-124 °C (lit.)

SMILES string

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

InChI

1S/C6H2Cl2O2/c7-4-1-3(9)2-5(8)6(4)10/h1-2H

InChI key

JCARTGJGWCGSSU-UHFFFAOYSA-N

Related Categories

General description

2,6-Dichloro-1,4-benzoquinone (DCBQ, 2,6-DCBQ) is a halobenzoquinone. Halobenzoquinones are disinfection byproducts (DBPs) found in drinking water. They are capable of producing reactive oxygen species and causing oxidative damage to proteins and DNA in T24 human bladder carcinoma cells. UV-induced transformation of DCBQ in drinking water has been reported. Detection of DCBQ in drinking water by liquid chromatography-ESI tandem mass spectrometry has been reported.

Application

2,6-Dichloro-1,4-benzoquinone is the suitable reagent used to in a study to evaluate the diffusion coefficients (D) for a family of quinones, nitroaromatics, ferrocenes and aromatic hydrocarbon compounds, in acetonitrile by single potential step chronoamperometry. It may be used in the preparation of :
  • 2,3,5-Trichloro-1,4-dihydroquinone
  • 2,3,5-trichloro-1,4-benzoquinone
  • 2,6-Dichloro-1,4-dihydroquinone

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Jinhua Li et al.
Toxicological sciences : an official journal of the Society of Toxicology, 141(2), 335-343 (2014-05-09)
Halobenzoquinones (HBQs) are a new class of drinking water disinfection byproducts (DBPs) and are capable of producing reactive oxygen species and causing oxidative damage to proteins and DNA in T24 human bladder carcinoma cells. However, the exact mechanism of the
Kai He et al.
Journal of hazardous materials, 351, 98-107 (2018-03-10)
Anthropogenic compounds accidentally released to the environment could be important precursors of disinfection byproducts (DBPs) in drinking water treatment processes. In this study, the haloacetic acid formation potentials (HAAFPs) of 155 anthropogenic compounds listed on the Japanese pollutant release and
A Magnuson et al.
Biochemistry, 36(11), 3254-3261 (1997-03-18)
The binding of Mn2+ to manganese-depleted photosystem II was investigated after chemical modification of histidyl and carboxylic acid residues in the presence or absence of the native manganese cluster. K(M) values for Mn2+ were determined from steady-state electron transfer between
Masako Iwai et al.
Photosynthesis research, 87(3), 313-322 (2006-05-16)
PS II-H is a small hydrophobic protein that is universally present in the PS II core complex of cyanobacteria and plants. The role of PS II-H was studied by directed mutagenesis and biochemical analysis in the thermophilic cyanobacterium Thermosynechococcus elongatus
A toxic disinfection by-product, 2,6-dichloro-1,4-benzoquinone, identified in drinking water.
Feng Qin et al.
Angewandte Chemie (International ed. in English), 49(4), 790-792 (2009-12-22)
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