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 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:33081 Y
ChemSpider	8807 Y
ECHA InfoCard	100.005.380
PubChem	9161
UNII	1Z25C36811 Y
InChI InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H Y Key: HXGDTGSAIMULJN-UHFFFAOYSA-N Y 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	152.20 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
Hazards
R-phrases	R22 R36 R37 R38
S-phrases	S26 S36 S37 S39
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

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

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
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; Hideo Nagashima (1925). "Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Cluster as the Catalyst". Org. Synth. 82: 188. ; Coll. Vol., 11, p. 1