Acenaphthylene

Acenaphthylene
Names
	Preferred IUPAC name Acenaphthylene
	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
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[1]
Heat capacity (C)	166.4 J mol−1 K−1
Enthalpy of fusion (ΔfH⦵fus)	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 [77 °F], 100 kPa). 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.^[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

^ 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.
^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
^ ^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.
^ 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.
^ 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.
^ Ullmann, 4th ed., 21, 70
^ 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.

[iupac2013-1] 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.

[crc-2] John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.

[Ullmanns-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.

[Connelly-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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v t e Polycyclic aromatic hydrocarbons
2 rings	Butalene Azulene Naphthalene
3 rings	Acenaphthene Acenaphthylene Anthracene Fluorene Phenalene Phenanthrene
4 rings	Benz[a]anthracene Benzo[a]fluorene Benzo[c]fluorene Benzo[c]phenanthrene Chrysene Fluoranthene Pyrene Tetracene Triphenylene Tricyclobutabenzene
5 rings	Benz[e]acephenanthrylene Benzopyrene Benzo[a]pyrene Benzo[e]pyrene 6H-Benzo[cd]pyrene(Olympicene) Benzo[a]fluoranthene Benzo[b]fluoranthene Benzo[j]fluoranthene Benzo[k]fluoranthene trans-Bicalicene Dibenz[a,h]anthracene Dibenz[a,j]anthracene Pentacene Pentaphene Perylene Picene Tetraphenylene
6 rings	Anthanthrene Benzo[ghi]perylene Corannulene Dibenzopyrenes Hexacene Triangulene Zethrene
7+ rings	Coronene Dicoronylene Diindenoperylene Heptacene Hexabenzocoronene (Hexa-cata-) Kekulene Ovalene Rubicene Rubrene Sumanene Superphenalene Trinaphthylene Truxene
General classes	Acene Circulene Cyclacene Helicene Phenacene