Skip to Content
MilliporeSigma
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C8H8O2
CAS Number:
137-18-8
Molecular Weight:
136.15
Beilstein/REAXYS Number:
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

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

Related Categories

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 8

1 of 8

Trimethylhydroquinone 97%

Sigma-Aldrich

T76503

Trimethylhydroquinone

2,3-Dimethoxy-5-methyl-p-benzoquinone apoptosis inducer

Sigma-Aldrich

D9150

2,3-Dimethoxy-5-methyl-p-benzoquinone

2,5-Di-tert-butyl-1,4-benzoquinone 99%

Sigma-Aldrich

419648

2,5-Di-tert-butyl-1,4-benzoquinone

2,5-Dichloro-1,4-benzoquinone 98%

Sigma-Aldrich

431974

2,5-Dichloro-1,4-benzoquinone

2,6-Di-tert-butyl-1,4-benzoquinone 98%

Sigma-Aldrich

153931

2,6-Di-tert-butyl-1,4-benzoquinone

p-Benzoquinone reagent grade, ≥98%

Sigma-Aldrich

B10358

p-Benzoquinone

Tetrafluoro-1,4-benzoquinone 97%

Sigma-Aldrich

104353

Tetrafluoro-1,4-benzoquinone

5,8-Dihydroxy-1,4-naphthoquinone technical grade

Sigma-Aldrich

388513

5,8-Dihydroxy-1,4-naphthoquinone

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
Oana Cramariuc et al.
Journal of molecular modeling, 19(2), 697-704 (2012-09-27)
The effect of a strong electric field generated by molecular dipoles on the ground state electronic structure and the Q and B states as well as the lowest charge transfer (CT) excited state of porphine-2,5-dimethyl-1,4-benzoquinone (PQ) complex has been investigated
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
Wiesława Zaborska et al.
Bioorganic chemistry, 35(3), 233-242 (2006-12-16)
In this work we studied the reaction of four quinones, 1,4-benzoquinone (1,4-BQ), 2,5-dimethyl-1,4-benzoquinone (2,5-DM-1,4-BQ), tetrachloro-1,4-benzoquinone (TC-1,4-BQ) and 1,4-naphthoquinone (1,4-NQ) with jack bean urease in phosphate buffer, pH 7.8. The enzyme was allowed to react with different concentrations of the quinones
Catherine E Sansom et al.
Journal of natural products, 70(12), 2042-2044 (2007-12-07)
Bioactivity-directed isolation work on the endemic New Zealand brown alga Perithalia capillaris, seeking anti-inflammatory compounds, led to a new bis-prenylated quinone ( 4). This compound inhibited superoxide production by human neutrophils in vitro (IC 50 2.1 microM), but was more
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service