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39579

Sigma-Aldrich

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
Beilstein:
2041348
EC Number:
205-283-6
MDL number:
MFCD00041737
UNSPSC Code:
12352100
PubChem Substance ID:
57649863
NACRES:
NA.22

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

SMILES string

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

InChI

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

InChI key

MYKLQMNSFPAPLZ-UHFFFAOYSA-N

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.

Application

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

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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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
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
Dale E Ward et al.
Organic letters, 9(15), 2843-2846 (2007-06-22)
The total synthesis of (-)-cyathin A3 is described. The key step involves an unusual enantioselective Diels-Alder reaction of 2,5-dimethyl-1,4-benzoquinone with 2,4-bis(trimethylsilyloxy)-1,3-pentadiene, using Mikami's catalyst [(R)-BINOL + Cl2Ti(OiPr)2 + 4 A mol sieves] modified by addition of Mg and SiO2. Because
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.
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