B10358

Sigma-Aldrich

p-Benzoquinone

greener alternative

reagent grade, ≥98%

Synonym(s):
Quinone
Linear Formula:
C6H4(=O)2
CAS Number:
Molecular Weight:
108.09
Beilstein/REAXYS Number:
773967
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21
Pricing and availability is not currently available.

Quality Level

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
Learn more about the Principles of Green Chemistry.

mp

113-115 °C (lit.)

solubility

water: soluble 14.7 g/L at 20 °C

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

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
Free radical inhibitor
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.

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

Packaging

5, 100, 500 g in glass bottle
1 kg in glass bottle

Signal Word

Danger

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T,N

Risk Statement

23/25-36/37/38-50

Safety Statement

26-28-45-61

RIDADR

UN 2587 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

Certificate of Analysis
Certificate of Origin
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)
Indian J. Chem. B, 32, 1113-1113 (1993)
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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