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Key Documents

8.02410

Sigma-Aldrich

p-Benzoquinone

for synthesis

Synonym(s):

p-Benzoquinone, p-Quinone, 1,4-Benzoquinone, 1,4-Cyclohexadiene-3,6-dione

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About This Item

Empirical Formula (Hill Notation):
C6H4O2
CAS Number:
106-51-4
Molecular Weight:
108.09
MDL number:
MFCD00001591
UNSPSC Code:
12352115
EC Index Number:
203-405-2
NACRES:
NA.22

vapor pressure

0.12 hPa ( 20 °C)

Quality Level

200

form

solid

autoignition temp.

560 °C

potency

130 mg/kg LD50, oral (Rat)

pH

4 (20 °C, 1 g/L in H2O)

mp

110-113 °C

solubility

10 g/L

density

1.32 g/cm3 at 20 °C

bulk density

700 kg/m3

storage temp.

2-30°C

InChI

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

InChI key

AZQWKYJCGOJGHM-UHFFFAOYSA-N

Application

p-Benzoquinone can be used as:
  • A free-radical inhibitor.
  • A catalyst to synthesize highly site-selective N1-alkylated benzotriazoles by N1-alkylation of benzotriazoles with diazo compounds.
  • A hydrogen acceptor and two electron oxidant in Pd-catalyzed Wacker oxidation of aryl olefins aldehydes.
  • A redox mediator in Pd-catalyzed anaerobic electrooxidative homocoupling of aryl-boron derivatives.

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

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

Certificates of Analysis (COA)

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Peili Teo et al.
Organic letters, 14(13), 3237-3239 (2012-06-15)
A method for efficient and aldehyde-selective Wacker oxidation of aryl-substituted olefins using PdCl(2)(MeCN)(2), 1,4-benzoquinone, and t-BuOH in air is described. Up to a 96% yield of aldehyde can be obtained, and up to 99% selectivity can be achieved with styrene-related
Ruthenium-catalyzed carbon-carbon formation to synthesize tetraarylethanes and tetraarylxylylene through dechlorinative dimeric reaction
Li, Yanjun, et al.
Journal of Organometallic Chemistry, 687(1), 12-15 (2003)
Jingya Yang et al.
Organic letters, 22(18), 7284-7289 (2020-09-10)
A visible-light-promoted highly site-selective N1-alkylation of benzotriazoles with diazo compounds has been achieved under mild and metal-free conditions. Using cheap, readily available p-benzoquinone (PBQ) as a catalyst, a wide range of benzotriazoles and diazo compounds are reacted, providing N1-alkylated benzotriazoles
Pd (OAc) 2/p-Benzoquinone-Catalyzed Anaerobic Electrooxidative Homocoupling of Arylboronic Acids, Arylboronates and Aryltrifluoroborates in DMF and/or Water
Amatore C, et al.
European Journal of Organic Chemistry, 4567-4570 (2008)

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