Acenaphthylene

Not to be confused with Acenaphthene.
Acenaphthylene
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
Acenaphthylene[1]
Other names
Cyclopenta[de]naphthalene
Acenaphthalene
Tricyclo[6.3.1.04,12]dodeca-1(12),2,4,6,8,10-hexaene[citation needed]
Tricyclo[6.3.1.04,12]dodecahexaene[citation needed]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.380 Edit this at Wikidata
UNII
  • InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H checkY
    Key: HXGDTGSAIMULJN-UHFFFAOYSA-N checkY
  • InChI=1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
    Key: HXGDTGSAIMULJN-UHFFFAOYAQ
  • c3cc1cccc2\C=C/c(c12)c3
  • c1cc2cccc3c2c(c1)C=C3
Properties
C12H8
Molar mass 152.196 g·mol−1
Appearance Yellow crystals
Density 0.8987 g cm−3
Melting point 91.8 °C (197.2 °F; 364.9 K)
Boiling point 280 °C (536 °F; 553 K)
Insoluble
Solubility in ethanol very soluble
Solubility in diethyl ether very soluble
Solubility in benzene very soluble
Solubility in chloroform soluble
Thermochemistry[1][2]
166.4 J mol−1 K−1
Enthalpy of fusion (ΔfH⦵fus)
 186.7 kJ/mol
69 kJ/mol
71.06 kJ/mol
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H302, H310, H315, H319, H330, H335
P260, P262, P264, P270, P271, P280, P284, P301+P312, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
Flash point 122 °C (252 °F; 395 K)
Related compounds
Related compounds
 acenaphthene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Acenaphthylene, a polycyclic aromatic hydrocarbon is an ortho- and peri-fused tricyclic hydrocarbon. The molecule resembles naphthalene with positions 1 and 8 connected by a -CH=CH- unit. It is a yellow solid.[3] Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.

Occurrence

Acenaphthylene occurs as about 2% of coal tar. It is produced industrially by gas phase dehydrogenation of acenaphthene.[3]

Reactions

Hydrogenation gives the more saturated compound acenaphthene. Chemical reduction affords the radical anion sodium or potassium acenaphthalenide, which is used as a strong reductant (E = -2.26 V vs FC).[4]

It functions as a ligand for some organometallic compounds.[5]

Uses

Polymerisation of acenaphthylene with acetylene in the presence of a Lewis acid catalyst gives electrically conductive polymers. Acenaphthylene possesses excellent properties as an antioxidant in cross-linked polyethylene and ethylene-propylene rubber. Thermal trimerization of acenaphthylene leads to decacyclene, which can be further processed to sulfur dyes.[6]

Toxicity

The no-observed-adverse-effect-level of acenaphthylene after repeated 28-day oral administration to both male and female rats was found to be 4 mg/kg/day.[7]

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 210. doi:10.1039/9781849733069-00130. ISBN 978-0-85404-182-4.
  2. ^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
  3. ^ a b Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 3527306730.
  4. ^ Connelly, Neil G.; Geiger, William E. (1996-01-01). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews. 96 (2): 877–910. doi:10.1021/cr940053x. ISSN 0009-2665. PMID 11848774.
  5. ^ Motoyama, Yukihiro; Itonaga, Chikara; Ishida, Toshiki; Takasaki, Mikihiro; Nagashima, Hideo (2005). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Carbonyl Cluster as the Catalyst". Organic Syntheses. 82: 188. doi:10.15227/orgsyn.082.0188.
  6. ^ Ullmann, 4th ed., 21, 70
  7. ^ Tanabe, S.; et al. (2017). "Toxicity of repeated 28-day oral administration of acenaphthylene in rats". Fundamental Toxicological Sciences. 4 (6): 247–259. doi:10.2131/fts.4.247.

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