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Merck

B10358

p-Benzoquinone

greener alternative

reagent grade, ≥98%, powder or crystals

Synonym(s):

Quinone

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About This Item

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

Product Name

p-Benzoquinone, reagent grade, ≥98%

InChI

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

InChI key

AZQWKYJCGOJGHM-UHFFFAOYSA-N

SMILES string

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

biological source

synthetic

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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sustainability

Greener Alternative Product

mp

113-115 °C (lit.)

solubility

water: soluble 14.7 g/L at 20 °C

functional group

ketone

greener alternative category

Aligned

storage temp.

room temp

Quality Level

200

Gene Information

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

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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

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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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

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 3

flash_point_f

170.6 °F - closed cup

flash_point_c

77 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP1025
0000514687
0000514687
0000502542
0000502542

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Electronic States and Spectra of p-Benzoquinone.
Trommsdorff HP.
J. Chem. Phys. , 56(11), 5358-5372 (1972)
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)
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)
Indian J. Chem. B, 32, 1113-1113 (1993)
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