1,4-Benzoquinone
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| 1,4-Benzoquinone | |
|---|---|
 |
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| General | |
| Systematic name | cyclohexa-2,5-diene-1,4-dione |
| Other names | p-benzoquinone; p-quinone |
| Molecular formula | C6H4O2 |
| SMILES | O=C/1\C=C/C(=O)\C=C\1 |
| Molar mass | 108.095 g/mol |
| Appearance | Yellow monoclinc prisms |
| CAS number | [106-51-4] |
| Properties | |
| Density and phase | Solid - 1.318 g/cm³ at 20°C |
| Solubility in water | ? g/100 ml (?°C)
Slightly soluble in water and petroleum ether. |
| Melting point | 115°C (388 K) |
| Boiling point | Sublimes |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | planar |
| Dipole moment | 0 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | toxic |
| NFPA 704 | |
| Flash point | ?°C |
| R/S statement | R: 23/25-36/37/38-50 S: 26-28-45-61 |
| RTECS number | DK2625000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | 1,2-benzoquinone quinones |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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1,4-Benzoquinone is the chemical compound with the formula of C6H4-1,4-O2. This aromatic six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is considered interesting because it is multifunctional: it exhibits properties of a ketone, forming an oxime, an oxidant, forming the dihydroxy derivative, and an alkene, undergoing addition reactions.
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[edit] 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.[2] It is also uses as a dienophile in Diels Alder reactions.[3]
[edit] Related 1,4-benzoquinones
A variety of derivatives are known. Illustrative examples:
- 1,4-Naphthoquinone, derived by oxidation of naphthalene with chromium trioxide.[4]
- Ubiquinone-1, a naturally occurring 1,4-benzoquinone.
- Chloro-p-benzoquinone (CAS no. [695-99-8])[5]
- Chloranil, 1,4-C6Cl4O2, a stronger oxidant than 1,4-benzoquinone.
[edit] See also
[edit] References
- ^ Yang, T.-K.; Shen, C.-Y. ”1,4-Benzoquinone” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI:10.1002/047084289.
- ^ Vogel, E.; Klug, W.; Breuer, A. “1,6-Methano[10]annulene” Organic Syntheses, Coll. Vol. 6, p.731 (1988); Vol. 54, p.11 (1974).
- ^ Oda, M.; Kawase, T.; Okada, T.; Enomoto, T. “2-Cyclohexene-1,4-dione” Organic Syntheses, Collected Volume 9, p.186 (1998).
- ^ E. A. Braude E. A.; Fawcett, J. S. “1,4-naphthoquinone” Organic Syntheses, Collected Volume 4, p.698 (1963).
- ^ Harman, R. E. ”Chloro-p-benzoquinone” Organic Syntheses, Collected Volume 4, p.148 (1963).
[edit] External links
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