1,4-Benzoquinone
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| 1,4-Benzoquinone | |
|---|---|
| Image:1,4-Benzochinon.svg | |
| Image:1,4-benzoquinone-3d.png | |
| IUPAC name | Cyclohexa-2,5-diene-1,4-dione |
| Other names | p-benzoquinone; p-quinone |
| Identifiers | |
| CAS number | |
| RTECS number | DK2625000 |
| SMILES | O=C/1\C=C/C(=O)\C=C\1 |
| Properties | |
| Molecular formula | C6H4O2 |
| Molar mass | 108.095 g/mol |
| Appearance | Yellow solid |
| Density | 1.318 g/cm3 at 20 °C, solid |
| Melting point |
115 °C |
| Boiling point |
Sublimes |
| Solubility in water | Slightly soluble |
| Solubility | Slightly soluble in pteroleum ether; soluble in acetone; very soluble in ethanol, benzene, diethyl ether |
| Hazards | |
| Main hazards | Toxic |
| R-phrases | R23/25 R36/37/38 |
| S-phrases | S26 S28 S45 S61 |
| Related Compounds | |
| Related compounds | 1,2-Benzoquinone |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
1,4-Benzoquinone is the chemical compound with the formula C6H4O2. This nonaromatic six-membered ring compound is the oxidized derivative of 1,4-hydroquinone.[1] The molecule is multifunctional: it exhibits properties of a ketone, forming an oxime; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions.
Contents |
Applications in organic synthesis
It is used as a hydrogen acceptor and oxidant in organic synthesis.[1] 1,4-Benzoquinone serves as a dehydrogenation reagent. It is also uses as a dienophile in Diels Alder reactions.[1]
Related 1,4-benzoquinones
A variety of derivatives and analogues are known. Illustrative examples:
- 1,4-Naphthoquinone, derived by oxidation of naphthalene with chromium trioxide.[1]
- 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, a stronger oxidant and dehydrogenation agent than 1,4-benzoquinone.[1]
- Ubiquinone-1, a naturally occurring 1,4-benzoquinone.
- Chloro-p-benzoquinone, (CAS no. [695-99-8])[1]
- Chloranil, 1,4-C6Cl4O2, a stronger oxidant and dehydrogenation agent than 1,4-benzoquinone.
See also
References
ar:بارا بنزو كينون de:1,4-Benzochinon
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
