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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:
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Quality Level

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.[1] The transformation of 2,5-DCHQ to 2-chloromaleylacetate using PcpA (Pcp = pentachlorophenol) protein, isolated from Escherichia coli has been investigated.[2] It is reported to be the degradation product of 2,4,5-trichlorophenoxyacetic acid[3][4] and γ-hexachlorocyclohexane.[5]

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

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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
Michael C Pirrung et al.
The Journal of organic chemistry, 67(23), 7919-7926 (2002-11-09)
Two total syntheses of the unsymmetrical bis-indolylquinone natural product demethylasterriquinone B1 (also known as L-783,281) have been accomplished. The first exploits a known base-promoted condensation of indoles with bromanil, which stops at monoaddition using the sterically hindered 2-isoprenylindole. This permits
Rate constants of elementary steps of the reversible chain reaction of N-phenyl-1,4-benzoquinonemonoimine with 2,5-dichlorohydroquinone.
Antonov AV and Varlamov VT
Russian Chemical Bulletin, 56(5), 883-889 (2007)
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
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

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