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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)

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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)
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
N Knoepfle et al.
Biochemistry, 38(5), 1582-1588 (1999-02-04)
The intrinsic chlorophyll protein CP 43, a component of photosystem II (PS II) in higher plants, green algae, and cyanobacteria, is encoded by the psbC gene. Oligonucleotide-directed mutagenesis was employed to introduce mutations into a segment of psbC that encodes
Ben-Zhan Zhu et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(10), 3698-3702 (2007-03-16)
The metal-independent decomposition of organic hydroperoxides and the formation of organic alkoxyl radicals in the absence or presence of halogenated quinones were studied with electron spin resonance (ESR) and the spin-trapping agent 5,5-dimethyl-1-pyrroline N-oxide (DMPO). We found that 2,5-dichloro-1,4-benzoquinone (DCBQ)
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