9,10-Dihydroanthracene: Difference between revisions
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info from Org. Syn. and Aldrich |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| Formula = C<sub>14</sub>H<sub>12</sub> |
| Formula = C<sub>14</sub>H<sub>12</sub> |
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| MolarMass = |
| MolarMass = 180.25 |
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| Appearance = white solid |
| Appearance = white solid |
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| Density = |
| Density = 0.88 g/mL |
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| MeltingPtC = 108 to 109 |
| MeltingPtC = 108 to 109 |
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| BoilingPtC = 312 |
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| Solubility = }} |
| Solubility = }} |
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| Section3 = {{Chembox Hazards |
| Section3 = {{Chembox Hazards |
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==Preparation== |
==Preparation== |
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Because the [[aromaticity]] is not compromised for the flanking rings, [[hydrogenation]] |
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]] under [[Bouveault–Blanc reduction]].<ref>K. C. Bass "9,10-Dihydroanthracene" Organic Syntheses, 1962, Vol. 42, p.48ff. {{DOI|10.15227/orgsyn.042.0048}}</ref> 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]]. |
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9,10-Dihydroanthracene can also be prepared by the [[Friedel-Crafts alkylation]] of [[benzyl chloride]] with itself, with aluminium chloride as a catalyst. |
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The [[bond dissociation energy]] for the 9- and 10-C-H bonds are estimated at 78 kcal/mol. Thus these bonds are about 20% weaker than typical C-H bonds. |
The [[bond dissociation energy]] for the 9- and 10-C-H bonds are estimated at 78 kcal/mol. Thus these bonds are about 20% weaker than typical C-H bonds. |
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Revision as of 05:32, 8 August 2015
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| Identifiers | |
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| ECHA InfoCard | 100.009.398 |
CompTox Dashboard (EPA)
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| Properties | |
| C14H12 | |
| Molar mass | 180.25 |
| Appearance | white solid |
| Density | 0.88 g/mL |
| 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).
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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 in various chemical reactions.[1]
Preparation
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 under Bouveault–Blanc reduction.[2] 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-C-H bonds are estimated at 78 kcal/mol. Thus these bonds are about 20% weaker than typical C-H bonds.
References
- ^ Gerd Collin, Hartmut Höke and Jörg Talbiersky "Anthracene" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a02_343.pub2
- ^ K. C. Bass "9,10-Dihydroanthracene" Organic Syntheses, 1962, Vol. 42, p.48ff. doi:10.15227/orgsyn.042.0048