Acenaphthylene

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.[2] Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.

Acenaphthylene

Skeletal formula Space-filling model
Names
Preferred IUPAC name Acenaphthylene[1]
Other names Cyclopenta[de]naphthalene Acenaphthalene Tricyclo[6.3.1.0^4,12]dodeca-1(12),2,4,6,8,10-hexaene Tricyclo[6.3.1.0^4,12]dodecahexaene
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/h1-8H Key: HXGDTGSAIMULJN-UHFFFAOYSA-N InChI=1/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H Key: HXGDTGSAIMULJN-UHFFFAOYAQ
SMILES c3cc1cccc2\C=C/c(c12)c3 c1cc2cccc3c2c(c1)C=C3
Properties
Chemical formula	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)
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
Enthalpy of vaporization (ΔfHvap)	69 kJ/mol
Enthalpy of sublimation (ΔfHsublim)	71.06 kJ/mol
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H310, H315, H319, H330, H335
GHS precautionary statements	P260, P261, P262, P264, P270, P271, P280, P284, P301+312, P302+350, P302+352, P304+340, P305+351+338, P310, P312, P320, P321, P322, P330, P332+313, P337+313, P361, P362, P363, P403+233
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).
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Infobox references

Occurrence

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

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).[3]

It functions as a ligand for some organometallic compounds.[4]

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.[5]

Toxicity

The no-observed-effect-level of acenaphthylene after repeated 28-day oral administration to both male and female rats was found to be 4 mg/kg/day.[6]

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. Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
3. N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. doi:10.1021/cr940053x
4. Motoyama, Yukihiro; Itonaga, Chikara; Ishida, Toshiki; Takasaki, Mikihiro; Nagashima, Hideo (2005). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Cluster as the Catalyst". 82: 188. doi:10.15227/orgsyn.082.0188. Cite journal requires |journal= (help)
5. Ullmann, 4th ed., 21, 70
6. 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.