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

A13162 p-Benzoquinone, 98+%

Codice CAS
106-51-4
Sinonimi
Quinone

Dimensioni Prezzo ($) Quantità Disponibilità
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

Proprietà chimiche

Formula
C6H4O2
Peso formula
108.10
Punto di fusione
112-115°
Punto di ebollizione
ca 180° subl.
Punto di infiammabilità
77°(171°F)
Densità
1.318
Solubilità
Soluble in water, ethanol, ether, methanol, benzene, acetone and ethyl acetate.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): 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.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Merck
14,8074
Beilstein
773967
Classe di rischio
6.1
Gruppo di imballaggio
II
Codice tariffe armonizzato
2914.69
TSCA
Yes
RTECS
DK2625000

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