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106-51-4 - p-Benzoquinone, 98+% - Quinone - A13162 - Alfa Aesar

A13162 p-Benzoquinone, 98+%

CAS Number
106-51-4
Synonyms
Quinone

Size Price ($) Quantity Availability
100g 22.04
250g 27.44
1000g 85.18
5000g 311.40
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p-Benzoquinone, 98+%

MDL
MFCD00001591
EINECS
203-405-2

Chemical Properties

Formula
C6H4O2
Formula Weight
108.10
Melting point
112-115°
Boiling Point
ca 180° subl.
Flash Point
77°(171°F)
Density
1.318
Solubility
Soluble in water, ethanol, ether, methanol, benzene, acetone and ethyl acetate.

Applications

p-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double- bond migration during olefin metathesis reactions. It is used as a precursor to hydroquinone which finds application in photography and as a reducing agent and an antioxidant in rubber production.

Notes

Light sensitive. Store in cool place. Incompatible and reacts violently with strong oxidizing agents.

Literature References

Mild reoxidant in palladium-catalyzed reactions, to convert Pd(0) back to Pd(II); see e.g.: Org. Synth. Coll., 8, 137 (1993). For use in the Pd-catalyzed oxidative addition of amines to electron-deficient alkenes, to give enamines, see Palladium(II)­ chloride, 11034. For the cis-1,4-stereo- and regioselective chloroacetoxylation of 1,3-dienes by Pd(OAc)2 and LiCl, in the presence of benzoquinone, see Palladium(II)­ acetate, 10516.

Reacts with allyl or isoprenyl tin derivatives in the presence of BF3 etherate to give ortho allyl-substituted quinones: Org. Synth. Coll., 9, 741 (1998). For a reaction scheme, see 2,3-Dimethoxy-5-methyl-1,4-benzoquinone, B24777.

Ajeel, M. A.; Aroua, M. K.; Daud, W. M. A. W. p-Benzoquinone Anodic Degradation by Carbon Black Diamond Composite Electrodes. Electrochim. Acta. 2015, 169, 46-51.

Papa, C. M.; Cesnik, A. J.; Evans, T. C.; Choi, K. S. Electrochemical Synthesis of Binary and Ternary Niobium-Containing Oxide Electrodes Using the p-Benzoquinone/Hydroquinone Redox Couple. Langmuir 2015, 31 (34), 9502-9510.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H331-H315-H319-H335-H400

Toxic if swallowed. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Very toxic to aquatic life.

Precautionary Statements: P261-P273-P280-P301+P310-P305+P351+P338-P304+P340-P311-P362-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,8074
Beilstein
773967
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2914.69
TSCA
Yes
RTECS
DK2625000

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