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8.02410

Sigma-Aldrich

p-Benzoquinone

for synthesis

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Synonym(s):
p-Benzoquinone, p-Quinone, 1,4-Benzoquinone, 1,4-Cyclohexadiene-3,6-dione
Empirical Formula (Hill Notation):
C6H4O2
CAS Number:
Molecular Weight:
108.09
MDL number:
EC Index Number:
203-405-2

vapor pressure

0.12 hPa ( 20 °C)

Quality Level

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

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1 of 4

This Item
1056504PHR1028195464
vibrant-m

8.02410

p-Benzoquinone

vibrant-m

1056504

1,4-Benzoquinone

vibrant-m

PHR1028

1,4-Benzoquinone

vibrant-m

195464

2,5-Dihydroxy-1,4-benzoquinone

Quality Level

200

Quality Level

-

Quality Level

300

Quality Level

100

storage temp.

2-30°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

density

1.32 g/cm3 at 20 °C

density

-

density

-

density

-

mp

110-113 °C

mp

113-115 °C (lit.)

mp

113-115 °C (lit.)

mp

235 °C (dec.) (lit.)

vapor pressure

0.12 hPa ( 20 °C)

vapor pressure

0.1 mmHg ( 25 °C)

vapor pressure

0.1 mmHg ( 25 °C)

vapor pressure

-

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.

signalword

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_germany

WGK 3

flash_point_f

170.6 °F - closed cup

flash_point_c

77 °C - closed cup


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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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