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39579

Sigma-Aldrich

2,5-Dimethyl-1,4-benzoquinone

≥98.0%

Sinonimo/i:

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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5 G
CHF 185.00
25 G
CHF 644.00

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Cambia visualizzazione
5 G
CHF 185.00
25 G
CHF 644.00

About This Item

Formula empirica (notazione di Hill):
C8H8O2
Numero CAS:
137-18-8
Peso molecolare:
136.15
Beilstein:
2041348
Numero CE:
205-283-6
Numero MDL:
MFCD00041737
Codice UNSPSC:
12352100
ID PubChem:
57649863
NACRES:
NA.22

CHF 185.00

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Saggio

≥98.0%

Punto di fusione

123-125 °C

Solubilità

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

Gruppo funzionale

ketone

Stringa SMILE

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
MYKLQMNSFPAPLZ-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

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.[1] It is present as one of the component of defensive secretion of opilionid Acanthopachylus aculeatus.[2] It has been investigated as inhibitor of jack bean urease in 50mM phosphate buffer, pH 7.0.[3]

Applicazioni

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

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H301,H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
WXBF5447V
WXBF4224V
WXBF3165V
WXBD7955V
WXBD9645V

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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
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
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.
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
Thomas Eisner et al.
The Journal of experimental biology, 207(Pt 8), 1313-1321 (2004-03-11)
The opilionid Acanthopachylus aculeatus was shown to produce a defensive secretion containing quinones (2,3-dimethyl-1,4-benzoquinone, 2,5-dimethyl-1,4-benzoquinone and 2,3,5-trimethyl-1,4-benzoquinone), confirming the findings reported nearly a half century ago in a classic study. The mechanism by which the opilionid puts the secretion to
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