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Fluoranthene

Names
Preferred IUPAC name Fluoranthene
Other names Benzofluorene Tetracyclohexadeca-1,3,5,7,9(16),10,12,14-octaene
Identifiers
CAS Number	206-44-0
3D model (JSmol)	Interactive image
Beilstein Reference	1907918
ChEBI	CHEBI:33083
ChEMBL	ChEMBL355014
ChemSpider	8800
ECHA InfoCard	100.005.376
EC Number	205-912-4
Gmelin Reference	262216
KEGG	C19425
PubChem CID	9154
UNII	360UOL779Z
UN number	1325, 3082
CompTox Dashboard (EPA)	DTXSID3024104
InChI InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10HKey: GVEPBJHOBDJJJI-UHFFFAOYSA-N InChI=1/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10HKey: GVEPBJHOBDJJJI-UHFFFAOYAL
SMILES c1ccc-2c(c1)-c3cccc4c3c2ccc4
Properties
Chemical formula	C16H10
Molar mass	202.256 g·mol
Appearance	Yellow to green needles
Density	1.252 g/cm (0 °C), solid
Melting point	110.8 °C (231.4 °F; 383.9 K)
Boiling point	375 °C (707 °F; 648 K)
Solubility in water	265 μg/L (25 °C)
Magnetic susceptibility (χ)	-138.0·10 cm/mol
Viscosity	0.652 cP at 20 °C
Structure
Molecular shape	Planar
Dipole moment	0.34 D
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H410
Precautionary statements	P273, P501
Flash point	210 °C (410 °F; 483 K)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Fluoranthene is a polycyclic aromatic hydrocarbon (PAH). The molecule can be viewed as the fusion of naphthalene and benzene unit connected by a five-membered ring. The chemical formula is C₁₆H₁₀. Although samples are often pale yellow, the compound is colorless. It is soluble in nonpolar organic solvents. It is a member of the class of PAHs known as non-alternant PAHs because it has rings other than those with six carbon atoms. It is a structural isomer of the alternant PAH pyrene. It is not as thermodynamically stable as pyrene. Its name is derived from its fluorescence under UV light.

Occurrence

Traces of fluoranthene is found in many combustion products, along with other PAHs. It results from incomplete combustion. Fluoranthene was originally isolated from coal tar pitch. It is still obtained from the high boiling fraction of coal tar, representing a few percent by weight.

Pollutant

Fluoranthene is one of the U.S. Environmental Protection Agency's 16 priority pollutant PAHs. Fluoranthene has been classified by the International Agency for Research on Cancer as a group 3 carcinogen, "not classifiable as to its carcinogenicity to humans", however it was found to possess carcinogenic properties in case of newborn mice according to short-term lung tumor assay (Busby et al., 1984). In 2019, fluoranthene was added to the Candidate List of Substances of Very High Concern (SVHCs) due to its persistent, bioaccumulative and toxic (PBT) and very persistent and very bioaccumulative (vPvB) properties. Its occurrence in food has been assessed.

Its biodegradation has been elucidated. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.

References

1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 206, 503. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
2. GHS: GESTIS 030010
3. ^ 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
4. "Archived copy" (PDF). Archived from the original (PDF) on 2012-09-11. Retrieved 2012-07-30.{{cite web}}: CS1 maint: archived copy as title (link)
5. "Six new substances added to the Candidate List ECHA/PR/19/01". Retrieved 2019-01-17.
6. Zelinkova, Zuzana; Wenzl, Thomas (2015). "The Occurrence of 16 EPA PAHs in Food – A Review". Polycyclic Aromatic Compounds. 35 (2–4): 248–284. doi:10.1080/10406638.2014.918550. PMC 4673601. PMID 26681897.
7. Seo, Jong-Su; Keum, Young-Soo; Li, Qing (2009). "Bacterial Degradation of Aromatic Compounds". International Journal of Environmental Research and Public Health. 6 (1): 278–309. doi:10.3390/ijerph6010278. PMC 2672333. PMID 19440284.

External links

• National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet
• Chemical Profile for FLUORANTHENE from Scorecard
• FLUORANTHENE Chemical Fact Sheet by Spectrum Laboratories
• TOXICITY SUMMARY FOR FLUORANTHENE August 1993

• Polycyclic aromatic hydrocarbons
• Tetracyclic compounds
• PBT substances