Chemistry:Fluoranthene

Fluoranthene
Names
	Preferred IUPAC name Fluoranthene
	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
CAS Number	206-44-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1907918
ChEBI	CHEBI:33083 ;
ChEMBL	ChEMBL355014 ;
ChemSpider	8800 ;
EC Number	205-912-4;
Gmelin Reference	262216
KEGG	C19425 ;
PubChem CID	9154;
UNII	360UOL779Z ;
UN number	1325, 3082
	InChI InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H Key: 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/h1-10H Key: GVEPBJHOBDJJJI-UHFFFAOYAL;
	SMILES c1ccc-2c(c1)-c3cccc4c3c2ccc4;
Properties
Chemical formula	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)
Solubility in water	265 μg/L (25 °C)
Magnetic susceptibility (χ)	-138.0·10−6 cm3/mol
Viscosity	0.652 cP at 20 °C
Structure
Molecular shape	Planar
Dipole moment	0.34 D
Hazards
GHS pictograms
GHS Signal word	warning
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).
	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. 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

↑ 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.
↑ GHS: GESTIS 030010
↑ ^3.0 ^3.1 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
↑ "Archived copy". http://cira.ornl.gov/documents/FLUORANT.pdf.
↑ "Six new substances added to the Candidate List ECHA/PR/19/01". https://echa.europa.eu/-/six-new-substances-added-to-the-candidate-list.
↑ 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. PMID 26681897.
↑ 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. PMID 19440284.

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[iupac2013-1] 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

[Ullmanns-3] 3.0 ^3.1 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

[4] "Archived copy". http://cira.ornl.gov/documents/FLUORANT.pdf.

[5] "Six new substances added to the Candidate List ECHA/PR/19/01". https://echa.europa.eu/-/six-new-substances-added-to-the-candidate-list.

[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. 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. PMID 19440284.

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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 Benzo[a]fluoranthene Benzo[b]fluoranthene Benzo[j]fluoranthene Benzo[k]fluoranthene trans-Bicalicene Dibenz[a,h]anthracene Dibenz[a,j]anthracene Olympicene Pentacene Perylene Picene Tetraphenylene
6+ rings	Anthanthrene Benzo[ghi]perylene Circulene Corannulene Coronene Dicoronylene Diindenoperylene Heptacene Hexacene Kekulene Ovalene Zethrene
General classes	Acene Helicene Phenacene

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Preferred IUPAC name Fluoranthene^[1]
Other names Benzo[jk]fluorene Tetracyclo[7.6.1.0^5,16.0^10,15]hexadeca-1,3,5,7,9(16),10,12,14-octaene^{[citation needed]}
Identifiers
CAS Number	206-44-0^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1907918
ChEBI	CHEBI:33083^Y
ChEMBL	ChEMBL355014^Y
ChemSpider	8800^Y
EC Number	205-912-4
Gmelin Reference	262216
KEGG	C19425^Y
PubChem CID	9154
UNII	360UOL779Z^Y
UN number	1325, 3082
InChI InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H^Y Key: GVEPBJHOBDJJJI-UHFFFAOYSA-N^Y 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
SMILES c1ccc-2c(c1)-c3cccc4c3c2ccc4
Properties
Chemical formula	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)
Solubility in water	265 μg/L (25 °C)
Magnetic susceptibility (χ)	-138.0·10⁻⁶ cm³/mol
Viscosity	0.652 cP at 20 °C
Structure
Molecular shape	Planar
Dipole moment	0.34 D
Hazards
GHS pictograms
GHS Signal word	warning
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 ^YN ?)
Infobox references

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