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Acenaphthylene

Names
Preferred IUPAC name Acenaphthylene
Other names Cyclopentanaphthalene Acenaphthalene Tricyclododeca-1(12),2,4,6,8,10-hexaene Tricyclododecahexaene
Identifiers
CAS Number	208-96-8
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:33081
ChemSpider	8807
ECHA InfoCard	100.005.380
PubChem CID	9161
UNII	1Z25C36811
CompTox Dashboard (EPA)	DTXSID3023845
InChI InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8HKey: HXGDTGSAIMULJN-UHFFFAOYSA-N InChI=1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8HKey: HXGDTGSAIMULJN-UHFFFAOYAQ
SMILES c3cc1cccc2\C=C/c(c12)c3 c1cc2cccc3c2c(c1)C=C3
Properties
Chemical formula	C12H8
Molar mass	152.196 g·mol
Appearance	Yellow crystals
Density	0.8987 g cm
Melting point	91.8 °C (197.2 °F; 364.9 K)
Boiling point	280 °C (536 °F; 553 K)
Solubility in water	Insoluble
Solubility in ethanol	very soluble
Solubility in diethyl ether	very soluble
Solubility in benzene	very soluble
Solubility in chloroform	soluble
Thermochemistry
Heat capacity (C)	166.4 J mol K
Enthalpy of fusion (ΔfHfus)	186.7 kJ/mol
Enthalpy of vaporization (ΔfHvap)	69 kJ/mol
Enthalpy of sublimation (ΔfHsublim)	71.06 kJ/mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H310, H315, H319, H330, H335
Precautionary statements	P260, P261, P262, P264, P270, P271, P280, P284, P301+P312, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, 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 , 100 kPa). Y verify (what is  ?) Infobox references

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. 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.

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).

It functions as a ligand for some organometallic compounds.

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.

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.

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. ^ 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.

• Polycyclic aromatic hydrocarbons
• Tricyclic compounds