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{{Short description|Chemical compound}}
⚫
{{DISPLAYTITLE:Benz(''a'')anthracene}}
{{correct title|reason=bracket|Benz[''a'']anthracene}}
{{Correct title|reason=bracket|edit=substitution|Benz[''a'']anthracene}}
{{Chembox
{{Chembox
| Watchedfields = changed
| verifiedrevid = 396296498
| verifiedrevid = 459859965
|Name=Benzo[''a'']anthracene
⚫
|Name=Benz[''a'']anthracene
|ImageFile=Benzanthracene.png
|ImageFile=Benzanthracene.png
|ImageSize=200px
|ImageSize=200px
|ImageFile1=Benzanthracene-3D-balls.png
| ImageFile1 = Benz(a)anthracene molecule ball.png
|IUPACName=benz[''a'']anthracene
| ImageAlt1 = Ball-and-stick model of the benz[''a'']anthracene molecule
| PIN = Tetraphene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 208 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
|OtherNames= Benzanthracene; Benzanthrene; 1,2-Benzanthracene; Benzo[''b'']phenanthrene; Tetraphene
|OtherNames = Benz[''a'']anthracene<br />Benzanthracene<br />Benzanthrene<br />1,2-Benzanthracene<br />Benzo[''b'']phenanthrene<br />Tetracyclo[8.8.0.0<sup>2,7</sup>.0<sup>12,17</sup>]octadeca-1,3,5,7,9,11,13,15,17-nonaene{{cn|date=May 2019}}
|Section1= {{Chembox Identifiers
|Section1= {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| PubChem = 5954
| ChEBI = 51348
⚫
| PubChem = 5954
| InChI = 1/C18H12/c1-2-7-15-12-18-16(11-14(15)6-1)10-9-13-5-3-4-8-17(13)18/h1-12H
| InChI = 1/C18H12/c1-2-7-15-12-18-16(11-14(15)6-1)10-9-13-5-3-4-8-17(13)18/h1-12H
| InChIKey = DXBHBZVCASKNBY-UHFFFAOYAM
| InChIKey = DXBHBZVCASKNBY-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H12/c1-2-7-15-12-18-16(11-14(15)6-1)10-9-13-5-3-4-8-17(13)18/h1-12H
| StdInChI = 1S/C18H12/c1-2-7-15-12-18-16(11-14(15)6-1)10-9-13-5-3-4-8-17(13)18/h1-12H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DXBHBZVCASKNBY-UHFFFAOYSA-N
| StdInChIKey = DXBHBZVCASKNBY-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5739
| ChemSpiderID = 5739
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| SMILES = c1ccc2c(c1)ccc3c2cc4ccccc4c3
| UNII = C5PLF6152K
⚫
| SMILES = c1ccc2c(c1)ccc3c2cc4ccccc4c3
| MeSHName=
| MeSHName=
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14317
| KEGG = C14317
}}
}}
|Section2= {{Chembox Properties
|Section2= {{Chembox Properties
| C=18
| Formula=C<sub>18</sub>H<sub>12</sub>
| H=12
| MolarMass = 228.2879
| Appearance = solid
| Appearance = White solid
| Density= 1.19 g/cm<sup>3</sup>
| Density= 1.19 g/cm<sup>3</sup>
| MeltingPtC = 158
| MeltingPtC = 158
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}}
}}
|Section3= {{Chembox Hazards
|Section3= {{Chembox Hazards
| FlashPtC = 209.1
|meltingpoint= 54
| FlashPt=209.1 °C
}}
}}
}}
}}


'''Benz[''a'']anthracene''' is a [[polycyclic aromatic hydrocarbon]] with the [[chemical formula]] C<sub>18</sub>H<sub>12</sub>.
'''Benz[''a'']anthracene''' or '''benzo[''a'']anthracene''' is a [[polycyclic aromatic hydrocarbon]] with the [[chemical formula]] C<sub>18</sub>H<sub>12</sub>.<ref>{{Cite book|title=The MAK-Collection for Occupational Health and Safety|pages = 231–242|date=2002|publisher=Wiley-VCH Verlag GmbH & Co. KGaA|isbn=9783527600410|language=en|doi=10.1002/3527600418.mb5655e0027|chapter = Benzo&#91;a&#93;anthracene &#91;MAK Value Documentation, 2012&#93;}}</ref> It is produced during incomplete combustion of organic matter.

Benz[''a'']anthracene is one of carcinogenic constituents of [[tobacco smoke]].<ref name="TalhoutSchulz2011">{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482|doi-access=free}}</ref>


==See also==
==See also==
* [[Tetracene]], also known as benzo[''b'']anthracene
* [[Tetracene]], also known as benz[''b'']anthracene

==References==
{{Reflist}}

==External links==
* [https://www.atsdr.cdc.gov/toxprofiledocs/index.html?id=122&tid=25 Toxic Substances Portal - Polycyclic Aromatic Hydrocarbons] A resource summarizing many toxicological aspects of benzanthracene and other polycyclic aromatic hydrocarbons.


{{PAHs}}
{{PAHs}}
{{hydrocarbon-stub}}
{{Aryl hydrocarbon receptor modulators}}
⚫
[[Category:Polycyclic aromatic hydrocarbons]]


⚫
[[Category:Polycyclic aromatic hydrocarbons]]
[[ar:بنز (أ) أنثراسين]]
[[Category:IARC Group 2A carcinogens]]
[[fr:Benzanthracène]]
[[Category:Tetracyclic compounds]]
[[nl:Benzo(a)anthraceen]]
[[Category:PBT substances]]
[[th:เบนโซเอแอนทราซีน]]

Latest revision as of 23:47, 29 December 2023

The correct title of this article is Benz[a]anthracene. The substitution of any brackets is due to technical restrictions.
Benz[a]anthracene
Ball-and-stick model of the benz[a]anthracene molecule
Names
Preferred IUPAC name
Tetraphene[1]
Other names
Benz[a]anthracene
Benzanthracene
Benzanthrene
1,2-Benzanthracene
Benzo[b]phenanthrene
Tetracyclo[8.8.0.02,7.012,17]octadeca-1,3,5,7,9,11,13,15,17-nonaene[citation needed]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.255 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C18H12/c1-2-7-15-12-18-16(11-14(15)6-1)10-9-13-5-3-4-8-17(13)18/h1-12H checkY
    Key: DXBHBZVCASKNBY-UHFFFAOYSA-N checkY
  • InChI=1/C18H12/c1-2-7-15-12-18-16(11-14(15)6-1)10-9-13-5-3-4-8-17(13)18/h1-12H
    Key: DXBHBZVCASKNBY-UHFFFAOYAM
  • c1ccc2c(c1)ccc3c2cc4ccccc4c3
Properties
C18H12
Molar mass 228.294 g·mol−1
Appearance White solid
Density 1.19 g/cm3
Melting point 158 °C (316 °F; 431 K)
Boiling point 438 °C (820 °F; 711 K)
Hazards
Flash point 209.1 °C (408.4 °F; 482.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Benz[a]anthracene or benzo[a]anthracene is a polycyclic aromatic hydrocarbon with the chemical formula C18H12.[2] It is produced during incomplete combustion of organic matter.

Benz[a]anthracene is one of carcinogenic constituents of tobacco smoke.[3]

See also

[edit]

References

[edit]
  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 208. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ "Benzo[a]anthracene [MAK Value Documentation, 2012]". The MAK-Collection for Occupational Health and Safety. Wiley-VCH Verlag GmbH & Co. KGaA. 2002. pp. 231–242. doi:10.1002/3527600418.mb5655e0027. ISBN 9783527600410.
  3. ^ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC 3084482. PMID 21556207.
[edit]
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