Acenaphthylene

Acenaphthylene
Names
	IUPAC name Acenaphthylene
	Systematic IUPAC name Tricyclo[6.3.1.04,12]dodeca-1(12),2,4,6,8,10-hexaene
	Other names Cycopenta[de]naphthalene, Acenaphthalene
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
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 is a polycyclic aromatic hydrocarbon. The molecule resembles naphthalene with positions 1 and 8 connected by a C₂H₂ 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 dehydrogenation of acenaphthene.^[1] More than 20% of the carbon in the universe may be associated with PAHs.^[2]

Reactions

Hydrogenation gives the more saturated compound acenaphthene.

It functions as a ligand for some organometallic compounds.^[3]

References

^ Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_227
^ Hoover, Rachel (February 21, 2014). "Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That". NASA. Retrieved February 22, 2014.
^ Yukihiro Motoyama, Chikara Itonaga, Toshiki Ishida, Mikihiro Takasaki, and Hideo Nagashima (1925). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Cluster as the Catalyst". Organic Syntheses. 82: 188{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 11, p. 1.

[Ullmanns-1] Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_227

[NASA-20140221-2] Hoover, Rachel (February 21, 2014). "Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That". NASA. Retrieved February 22, 2014.

[3] Yukihiro Motoyama, Chikara Itonaga, Toshiki Ishida, Mikihiro Takasaki, and Hideo Nagashima (1925). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Cluster as the Catalyst". Organic Syntheses. 82: 188{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 11, p. 1.

[1]

[2]

[3]

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 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