Acenaphthylene

Acenaphthylene
Skeletal formula
Space-filling model
Names
IUPAC name
Acenaphthylene
Systematic IUPAC name
Tricyclo[6.3.1.04,12]dodeca-1(12),2,4,6,8,10-hexaene
Other names
Cyclopenta[de]naphthalene, Acenaphthalene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.380
UNII
Properties
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)
Insoluble
Solubility in ethanol very soluble
Solubility in diethyl ether very soluble
Solubility in benzene very soluble
Solubility in chloroform soluble
Hazards
R-phrases (outdated) R22 R36 R37 R38
S-phrases (outdated) S26 S36 S37 S39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]

Reactions

Hydrogenation gives the more saturated compound acenaphthene. It functions as a ligand for some organometallic compounds.[2]

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.[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. ↑ 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". Organic Syntheses. 82: 188. ; Collective Volume, 11, p. 1
  3. ↑ 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. Retrieved November 6, 2017.
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