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Merck
CN

39579

2,5-Dimethyl-1,4-benzoquinone

≥98.0%

Synonym(s):

2,5-Dimethyl-2,5-cyclohexadiene-1,4-dione, 2,5-Dimethyl-p-benzoquinone, 2,5-Dimethyl-p-quinone, 2,5-Dimethylbenzoquinone, 2,5-Xyloquinone, 3,6-Dimethyl-p-benzoquinone

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About This Item

Empirical Formula (Hill Notation):
C8H8O2
CAS Number:
137-18-8
Molecular Weight:
136.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57649863
EC Number:
205-283-6
Beilstein/REAXYS Number:
2041348
MDL number:
MFCD00041737

Key Documents

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Product Name

2,5-Dimethyl-1,4-benzoquinone, ≥98.0%

InChI key

MYKLQMNSFPAPLZ-UHFFFAOYSA-N

InChI

1S/C8H8O2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3

SMILES string

CC1=CC(=O)C(C)=CC1=O

assay

≥98.0%

mp

123-125 °C

solubility

toluene: soluble 0.5 g/10 mL, clear to faintly turbid, yellow to brown

functional group

ketone

Related Categories

Application

2,5-Dimethyl-1,4-benzoquinone may be used in a key step involved in the total synthesis of (−)-cyathin A3.

General description

2,5-Dimethyl-1,4-benzoquinone is a quinone derivative. Its reaction with jack bean urease in phosphate buffer, pH 7.8 has been studied. It is present as one of the component of defensive secretion of opilionid Acanthopachylus aculeatus. It has been investigated as inhibitor of jack bean urease in 50mM phosphate buffer, pH 7.0.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7136V
WXBF5447V
WXBF4224V
WXBF3165V
WXBD7955V

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Wiesława Zaborska et al.
Journal of enzyme inhibition and medicinal chemistry, 17(4), 247-253 (2003-01-18)
1,4-benzoquinone (BQ) and 2,5-dimethyl-1,4-benzoquinone (DMBQ) were studied as inhibitors of jack bean urease in 50 mM phosphate buffer, pH 7.0. The mechanisms of inhibition were evaluated by progress curves studies and steady-state approach to data achieved by preincubation of the
M Floreani et al.
The Journal of pharmacology and experimental therapeutics, 260(2), 468-473 (1992-02-01)
In guinea pig and rat cardiac tissue, redox cycling benzoquinones (2,5-dimethyl-p-benzoquinone and duroquinone) and naphthoquinones (menadione and 2,3-dimethoxy-1,4-naphthoquinone) generated superoxide anion (O2-.) both through one- and two-electron reductions, the generation being significantly greater in guinea pig than in rat tissue.
S Kumazawa et al.
Journal of bacteriology, 154(1), 185-191 (1983-04-01)
Whole cells of photoanaerobically grown Chromatium sp. strain Miami PBS1071, a marine sulfur purple bacterium, oxidized H2 in the dark through the oxyhydrogen reaction at rates of up to 59 nmol of H2 per mg (dry weight) per min. H2
J Cao et al.
Biochimica et biophysica acta, 1015(2), 180-188 (1990-02-02)
Upon illumination, a dark-adapted photosynthetic sample shows time-dependent changes in chlorophyll (Chl) a fluorescence yield, known as the Kautsky phenomenon or the OIDPS transient. Based on the differential effects of electron acceptors such as 2,5-dimethyl-p-benzoquinone (DMQ) and 2,6-dichloro-p-benzoquinone (DCBQ) on
K Hashimoto et al.
Journal of biochemistry, 91(4), 1111-1120 (1982-04-01)
1. The dependences of the reduction of ferricytochrome c-555 in the reaction center-cytochrome c complex on the redox potential and pH were investigated using N,N,N',N'-tetramethyl-p-phenylenediamine (TMPD), ferrocyanide, and reduced 2,5-dimethyl-p-quinone as electron donors. 2. In the reduction of cytochrome c-555
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