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B10358

Sigma-Aldrich

p-Benzoquinone

greener alternative

reagent grade, ≥98%

Synonym(s):

Quinone

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About This Item

Linear Formula:
C6H4(=O)2
CAS Number:
106-51-4
Molecular Weight:
108.09
Beilstein:
773967
EC Number:
203-405-2
MDL number:
MFCD00001591
UNSPSC Code:
12352005
PubChem Substance ID:
57653913
NACRES:
NA.21

biological source

synthetic

Quality Level

200

grade

reagent grade

vapor density

3.73 (vs air)

vapor pressure

0.1 mmHg ( 25 °C)

Assay

≥98%

form

powder or crystals

autoignition temp.

815 °F

greener alternative product characteristics

Catalysis
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Greener Alternative Product

mp

113-115 °C (lit.)

solubility

water: soluble 14.7 g/L at 20 °C

greener alternative category

storage temp.

room temp

SMILES string

O=C1C=CC(=O)C=C1

InChI

1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H

InChI key

AZQWKYJCGOJGHM-UHFFFAOYSA-N

Gene Information

human ... ACHE(43) , BCHE(590) , CES1(1066)

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General description

p-Benzoquinone (PBQ) is a cyclic conjugated diketone. Its high-resolution photoelectron spectrum has been reported. The visible and near ultraviolet spectra of PBQ have been recorded and analyzed. Its addition as coagent has been reported to enhance the crosslinking rate of polypropylene initiated by the pyrolysis of peroxides. Its impact on hemoglobin (Hb) has been investigated based on immunoblots and mass spectral analysis of a smoker′s blood.
Free radical inhibitor
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Application

p-Benzoquinone may be used to form benzofuranone derivatives on reacting with anilides of β-aminocrotonic acids via Nenitzescu reaction.
Dienophile employed in Diels-Alder cycloadditions to form naphthoquinones, and 1,4-phenanthrenediones.
Oxidant used in first step of greener amine synthesis from terminal olefins by Wacker oxidation followed by transfer hydrogenation of the resultant imine.

Formal anti-Markovnikov hydroamination of terminal olefins

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Sol. 1 - Muta. 2 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

170.6 °F

Flash Point(C)

77 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Interaction of p-benzoquinone with hemoglobin in smoker's blood causes alteration of structure and loss of oxygen binding capacity.
Ghosh A, et al.
Toxicology Reports, 3, 295-305 (2016)
Electronic States and Spectra of p-Benzoquinone.
Trommsdorff HP.
J. Chem. Phys. , 56(11), 5358-5372 (1972)
Indian J. Chem. B, 32, 1113-1113 (1993)
On the photoelectron spectrum of p-benzoquinone.
Stanton JF, et al.
J. Chem. Phys. , 115(1), 1-4 (2001)
Peroxide-initiated crosslinking of polypropylene in the presence of p-benzoquinone.
Chodak I and Lazar M.
Journal of Applied Polymer Science, 32(6), 5431-5437 (1986)
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