9,10-Dihydroanthracene
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| Names | |
|---|---|
| Preferred IUPAC name 9,10-Dihydroanthracene | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.009.398 |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C14H12 | |
| Molar mass | 180.250 g·mol−1 |
| Appearance | White solid |
| Density | 1.19 g mL−1[1] |
| Melting point | 108 to 109 °C (226 to 228 °F; 381 to 382 K) |
| Boiling point | 312 °C (594 °F; 585 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
9,10-Dihydroanthracene is an organic compound that is derived from the polycyclic aromatic hydrocarbon anthracene. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H2 as a hydrogen-donor.[2]
Preparation
[edit]Because the aromaticity is not compromised for the flanking rings, anthracene is susceptible to hydrogenation at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/ethanol,[3] an application of the Bouveault–Blanc reduction. The reduction can be effected by magnesium as well. Finally, it can also be prepared by the coupling of benzyl chloride using aluminium chloride as a catalyst.
The bond dissociation energy for the 9- and 10- carbon–hydrogen bonds are estimated at 78 kcal mol−1. Thus these bonds are about 20% weaker than typical C–H bonds.
See also
[edit]- Triptycene — analogue with three phenyl rings
References
[edit]- ^ Reboul, J. P.; Oddon, Y.; Caranoni, C.; Soyfer, J. C.; Barbe, J.; Pèpe, G. (1987). "Structure du Dihydro-9,10 Anthracène. Support Tricyclique de Médicaments Psychotropes". Acta Crystallographica Section C Crystal Structure Communications. 43 (3): 537–539. Bibcode:1987AcCrC..43..537R. doi:10.1107/S010827018709512X.
- ^ Collin, Gerd; Höke, Hartmut; Talbiersky, Jörg (2006). "Anthracene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_343.pub2. ISBN 9783527303854.
- ^ Bass, K. C. (1962). "9,10-Dihydroanthracene". Organic Syntheses. 42: 48. doi:10.15227/orgsyn.042.0048.