Fluoranthene
Chemical structure of fluoranthene
Ball-and-stick model of fluoranthene
Names
Preferred IUPAC name
Fluoranthene[1]
Other names
Benzo[jk]fluorene
Tetracyclo[7.6.1.05,16.010,15]hexadeca-1,3,5,7,9(16),10,12,14-octaene[citation needed]
Identifiers
3D model (JSmol)
1907918
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.376 Edit this at Wikidata
EC Number
  • 205-912-4
262216
KEGG
UNII
UN number 1325, 3082
  • InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H checkY
    Key: GVEPBJHOBDJJJI-UHFFFAOYSA-N checkY
  • InChI=1/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H
    Key: GVEPBJHOBDJJJI-UHFFFAOYAL
  • c1ccc-2c(c1)-c3cccc4c3c2ccc4
Properties
C16H10
Molar mass 202.256 g·mol−1
Appearance Yellow to green needles
Density 1.252 g/cm3 (0 °C), solid
Melting point 110.8 °C (231.4 °F; 383.9 K)
Boiling point 375 °C (707 °F; 648 K)
265 μg/L (25 °C)
-138.0·10−6 cm3/mol
Viscosity 0.652 cP at 20 °C
Structure
Planar
0.34 D
Hazards
GHS labelling:[2]
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H410
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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. Although samples are often pale yellow, the compound is colorless. It is soluble in nonpolar organic solvents.[3] 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.[3]

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"[1] , however it was found to possess carcinogenic properties in case of newborn mice according to short-term lung tumor assay (Busby et al., 1984).[4] 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.[5] Its occurrence in food has been assessed. [6]

Its biodegradation has been elucidated. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.[7]

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. ^ a b 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

Polycyclic aromatic hydrocarbons
Categories