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Sigma-Aldrich

2,5-Dichlorohydroquinone

98%

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About This Item

Linear Formula:
Cl2C6H2(OH)2
CAS Number:
Molecular Weight:
179.00
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Assay

98%

mp

168-171 °C (lit.)

SMILES string

Oc1cc(Cl)c(O)cc1Cl

InChI

1S/C6H4Cl2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2,9-10H

InChI key

AYNPIRVEWMUJDE-UHFFFAOYSA-N

General description

2,5-Dichlorohydroquinone (2,5-DCHQ) is a hydroquinone derivative that can be synthesized by reducing 2,5-dichloroquinone using sodium dithionite (Na2S2O4). The kinetics of the reaction of 2,5-DCHQ and N-phenyl-1,4-benzoquinonemonoimine has been studied. The transformation of 2,5-DCHQ to 2-chloromaleylacetate using PcpA (Pcp = pentachlorophenol) protein, isolated from Escherichia coli has been investigated. It is reported to be the degradation product of 2,4,5-trichlorophenoxyacetic acid and γ-hexachlorocyclohexane.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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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K Miyauchi et al.
Journal of bacteriology, 180(6), 1354-1359 (1998-03-27)
Sphingomonas (formerly Pseudomonas) paucimobilis UT26 utilizes gamma-hexachlorocyclohexane (gamma-HCH), a halogenated organic insecticide, as a sole carbon and energy source. In a previous study, we showed that gamma-HCH is degraded to 2,5-dichlorohydroquinone (2,5-DCHQ) (Y. Nagata, R. Ohtomo, K. Miyauchi, M. Fukuda
S Oikawa et al.
Carcinogenesis, 17(12), 2733-2739 (1996-12-01)
p-Dichlorobenzene (p-DCB) has been reported to be carcinogenic for rodents, although it does not seem to be mutagenic in bacterial test systems. In this study, the mechanism of DNA damage by metabolites of p-DCB in the presence of metals was
Y Nagata et al.
Journal of bacteriology, 176(11), 3117-3125 (1994-06-01)
In Pseudomonas paucimobilis UT26, gamma-hexachlorocyclohexane (gamma-HCH) is converted to 2,5-dichloro-2,5-cyclohexadiene-1,4-diol (2,5-DDOL), which is then metabolized to 2,5-dichlorohydroquinone. Here, we isolated from the genomic library of UT26 two genes which expressed 2,5-DDOL dehydrogenase activity when they were transformed into P. putida
R A Haugland et al.
Applied and environmental microbiology, 56(5), 1357-1362 (1990-05-01)
Combined cell suspensions of the 2,4,5-trichlorophenoxyacetic acid (2,4,5-T)-metabolizing organism Pseudomonas cepacia AC1100, and the 2,4-dichlorophenoxyacetic acid (2,4-D)-metabolizing organism Alcaligenes eutrophus JMP134 were shown to effectively degrade either of these compounds provided as single substrates. These combined cell suspensions, however, poorly
Y Ohtsubo et al.
FEBS letters, 459(3), 395-398 (1999-10-20)
The pentachlorophenol (PCP) mineralizing bacterium Sphingomonas chlorophenolica ATCC39723 degrades PCP via 2,6-dichlorohydroquinone (2,6-DCHQ). The pathway converting PCP to 2,6-DCHQ has been established previously; however, the pathway beyond 2,6-DCHQ is not clear, although it has been suggested that a PcpA plays

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