9,10-Dihydroanthraceneis anorganic compoundthat is derived from thepolycyclic aromatic hydrocarbonanthracene.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 H2as ahydrogen-donor.[2]
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| Names | |
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| Preferred IUPAC name
9,10-Dihydroanthracene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.009.398 |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C14H12 | |
| Molar mass | 180.250g·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 theirstandard state(at 25 °C [77 °F], 100 kPa).
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Preparation
editBecause thearomaticityis not compromised for the flanking rings, anthracene is susceptible tohydrogenationat the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/ethanol,[3]an application of theBouveault–Blanc reduction.The reduction can be effected by magnesium as well. Finally, it can also be prepared by the coupling ofbenzyl chlorideusingaluminium chlorideas acatalyst.
Thebond dissociation energyfor 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.ISBN9783527303854.
- ^Bass, K. C. (1962). "9,10-Dihydroanthracene".Organic Syntheses.42:48.doi:10.15227/orgsyn.042.0048.