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

A13162 p-Benzoquinone, 98+%

Numéro de CAS
106-51-4
Synonymes
Quinone

Conditionnement Prix ($) Quantité Disponibilité
100g 23,10
250g 26,70
1000g 83,50
5000g 350,00
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p-Benzoquinone, 98+%

MDL
MFCD00001591
EINECS
203-405-2

Propriétés chimiques

Formule
C6H4O2
Poids moleculaire
108.10
Point de fusion
112-115°
Point d'ébullition
ca 180° subl.
Point d'éclair
77°(171°F)
Densité
1.318
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H331-H315-H319-H335

Toxic if swallowed. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280a-P301+P310a-P305+P351+P338-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF SWALLOWED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,8074
Beilstein
773967
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2914.69
TSCA
Yes
RTECS
DK2625000

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