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

A13162 p-Benzoquinone, 98+%

CAS-Nummer
106-51-4
Synonyme
Quinone

Größe Preis ($) Menge Verfügbarkeit
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

Chemische Eigenschaften

Formel
C6H4O2
Molmasse
108.10
Schmelzpunkt
112-115°
Siedepunkt
ca 180° subl.
Flammpunkt
77°(171°F)
Dichte
1.318
Löslichkeit
Soluble in water, ethanol, ether, methanol, benzene, acetone and ethyl acetate.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): 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.

Sicherheitshinweise: 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.

Weitere Referenzen

Merck
14,8074
Beilstein
773967
Gefahrenklasse
6.1
Verpackungsgruppe
II
Harmonized Tariff Code
2914.69
TSCA
Yes
RTECS
DK2625000

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