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Revision as of 12:00, 10 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').← Previous edit		Latest revision as of 03:05, 25 November 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,558 edits it comes from coal tar, probably nobody makes it.
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			{{short description|Polycyclic aromatic hydrocarbon composed of three fused benzene rings}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 437975835
			| Watchedfields = changed
	|ImageFile=Phenanthrene.png
			| verifiedrevid = 444046459
	|ImageSize=180px
	|ImageFile1=Phenanthrene-3D-balls.png		| ImageFile=Phenanthrene-numbering.svg
	|ImageSize1=180px		| ImageSize=180px
	|IUPACName=Phenanthrene		| ImageFile1=Phenanthrene molecule ball.png
			| ImageSize1=180px
	|OtherNames=
			| ImageAlt1 = Ball-and-stick model of the phenanthrene molecule
	|Section1= {{Chembox Identifiers
			| ImageFile2 = Phenanthrene C14H10.JPG
	| CASNo_Ref = {{cascite}}
			| ImageName2 = Phenanthrene
			| PIN = Phenanthrene <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
			|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=85-01-8		| CASNo=85-01-8
	| PubChem=995		| PubChem=995
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 28851
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C11422		| KEGG = C11422
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 448J8E5BST
			| UNII = 448J8E5BST
	| SMILES=c1ccc2c(c1)ccc3ccccc32
			| SMILES = C1=CC=C2C(=C1)C=CC3=CC=CC=C32
	| InChI=1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
			| EINECS = 266-028-2
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 970
			| InChI = 1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
			| InChIKey = YNPNZTXNASCQKK-UHFFFAOYAC
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = YNPNZTXNASCQKK-UHFFFAOYSA-N
			| RTECS =
			| MeSHName = C031181
			| Beilstein = 1905428
			| Gmelin = 28699
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
	| C=14|H=10		| C=14 | H=10
	| Appearance=Colorless solid		| Appearance=Colorless solid
	| Density=1.18 g/cm<sup>3</sup><ref name=GESTIS/>		| Density=1.18 g/cm<sup>3</sup><ref name=GESTIS/>
	| MeltingPtC=101		| MeltingPtC=101
	| Melting_notes = <ref name=GESTIS>{{GESTIS|CAS=85-01-8}}</ref>		| MeltingPt_ref = <ref name=GESTIS>{{GESTIS|ZVG=22900|CAS=85-01-8}}</ref>
	| BoilingPtC=332		| BoilingPtC=332
	| Boiling_notes = <ref name=GESTIS/>		| BoilingPt_ref = <ref name=GESTIS/>
	| Solubility=1.6 mg/L<ref name=GESTIS/>		| Solubility=1.6 mg/L<ref name=GESTIS/>
			| MagSus = −127.9·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| NFPA-H = 1|NFPA-F = 1|NFPA-R=0|NFPA-O =		| NFPA-H = 1|NFPA-F = 1|NFPA-R=0|NFPA-S =
	| MainHazards=		| MainHazards=
			| FlashPtC = 171
	| FlashPt={{convert|171|C|F}}<ref name=GESTIS/>
			| FlashPt_ref = <ref name=GESTIS/>
	| Autoignition=
			| AutoignitionPt =
			}}
			|Section4={{Chembox Structure
			| PointGroup = C<sub>2v</sub><ref>Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. P.&nbsp;443.</ref>
			| Dipole = 0 ]
	}}		}}
	}}		}}
	'''Phenanthrene''' is a ] composed of three fused ] rings. The name ''phenanthrene'' is a composite of ] and ]. In its pure form, it is found in ] and is a known ], ] skin to light.{{Citation needed|date=July 2011}} Phenanthrene appears as a white powder having blue fluorescence.		'''Phenanthrene''' is a ] (PAH) with formula C<sub>14</sub>H<sub>10</sub>, consisting of three fused ] rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.<ref name="factsheet">{{cite web |title=Phenanthrene Fact Sheet |url=https://archive.epa.gov/epawaste/hazard/wastemin/web/pdf/phenanth.pdf |website=archive.epa.gov |publisher=U.S. Environmental Protection Agency |access-date=19 July 2019}}</ref>
			Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure. Animal studies have shown that phenanthrene is a potential carcinogen.<ref name="factsheet" /> However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.<ref>{{cite web |title=Phenanthrene |website=Sigma-Alrdich |url=https://www.sigmaaldrich.com/catalog/product/aldrich/p11409}}</ref>
	The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as ].
			Phenanthrene's three fused rings are angled as in the ]s, rather than straight as in the ]s. The compounds with a phenanthrene skeleton but with nitrogen atoms in place of CH sites are known as ]s.
	==Chemistry==
	Phenanthrene is nearly insoluble in water but is soluble in most organic solvents such as ], ], ], ], ] and ].
			== History and etymology ==
	A classical phenanthrene synthesis is the Bardhan-Sengupta phenanthrene synthesis.<ref>chempensoftware.com </ref>
			Phenanthrene was discovered in ] in 1872 independently by ] (article manuscript received on November 1st<ref>{{Cite journal |last=Graebe |first=C. |date=1872 |title=Ueber einen neuen dem Anthracen isomeren Kohlenwasserstoff |url=https://books.google.com/books?id=cwaLZrjMd0oC&pg=PA861 |journal=Berichte der deutschen chemischen Gesellschaft |language=en |volume=5 |issue=2 |pages=861–863 |doi=10.1002/cber.18720050279 |issn=0365-9496}}</ref>) as well as by ] and his doctoral student {{Ill|Eugen Ostermayer|de}} (manuscript received on November 19th<ref>{{Cite journal |last=Ostermayer |first=E. |last2=Fittig |first2=R. |date=1872 |title=Ueber einen neuen Kohlenwasserstoff aus dem Steinkohlentheer |url=https://books.google.com/books?id=cwaLZrjMd0oC&pg=PA933 |journal=Berichte der deutschen chemischen Gesellschaft |language=en |volume=5 |issue=2 |pages=933–937 |doi=10.1002/cber.187200502100 |issn=0365-9496}}</ref> but Ostermayer's dissertation defended in August<ref>{{Cite book |last=Ostermayer |first=Eugen |url=https://books.google.com/books?id=K5NTAAAAcAAJ |title=Ueber einen neuen Kohlenwasserstoff im Steinkohlentheeröl: Inaugural-Dissertation |date=1872 |publisher=Druck v. Fues |language=de}}</ref>). Fittig and Ostermayer were able to determine the structure of the compound by oxidizing it first to a ] and then to ], and soon Graebe confirmed it by a synthesis from ].<ref>{{Cite journal |last=Graebe |first=C. |date=1873 |title=Ueber Synthese des Phenanthrens |url=https://books.google.com/books?id=vCxJAAAAYAAJ&pg=PA125 |journal=Berichte der deutschen chemischen Gesellschaft |language=en |volume=6 |issue=1 |pages=125–127 |doi=10.1002/cber.18730060147 |issn=0365-9496}}</ref>
			Prior to February 1873 Fittig sent a letter to Graebe where he proposed to name the hydrocarbon phenanthrene ({{Langx|de|Phenanthren}}) in order to account for its similarity to ] and ], which was swiftly adopted.<ref>{{Cite journal |last=Graebe |first=C. |date=1873 |title=Ueber das Verhalten der Chinone beim Erhitzen mit Natronkalk |url=https://books.google.com/books?id=vCxJAAAAYAAJ&pg=PA63 |journal=Berichte der deutschen chemischen Gesellschaft |volume=6 |issue=1 |pages=63–66 |doi=10.1002/cber.18730060124 |issn=0365-9496}}</ref>
	:]
			==Physical properties==
	The first step is an electrophilic aromatic substitution reaction, which is allowed when the diphosphorous pentoxide makes the alcohol a better leaving group. However, no alkenes outside of the initial aromatic ring are created. In the second step of this reaction 9,10-dihydrophenanthrene is oxidized with elemental ]. The aromatization of six-membered rings by selenium is not clearly understood, but it does produce H<sub>2</sub>Se.
			Phenanthrene is nearly insoluble in water but is soluble in most low-polarity organic solvents such as ], ], ], ], ] and ].
	Phenanthrene can also be obtained photochemically from certain ]s.
			Phenanthrene is fluorescent under ultraviolet light, exhibiting a large ].<ref>{{Cite web |title=Spectrum {{!}} AAT Bioquest |url=https://www.aatbio.com/fluorescence-excitation-emission-spectrum-graph-viewer/phenanthrene |access-date=2024-07-30 |website=www.aatbio.com}}</ref> It can be used in ].
			==Chemistry==
	Reactions of phenanthrene typically occur at the 9 and 10 positions, including:		Reactions of phenanthrene typically occur at the 9 and 10 positions, including:
	* ] to phenanthrenequinone with ] <ref>], Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) </ref>		* ] with ] gives gives ].<ref>], Coll. Vol.&nbsp;4, (1963); Vol.&nbsp;34, p.&nbsp;76 (1954).</ref>
	* ] to] gas and ] <ref> ], Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) .</ref>		* ] to 9,10-dihydrophenanthrene with ] gas and ]<ref>], Coll. Vol.&nbsp;4, (1963); Vol.&nbsp;34, p.&nbsp;31 (1954).</ref>
	* ] to 9-bromophenanthrene with ] <ref>], Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) .</ref>		* ] to 9-bromophenanthrene with ]<ref>], Coll. Vol.&nbsp;3, (1955); Vol.&nbsp;28, p.&nbsp;19 (1948).</ref>
	* ] to 2 and 3-phenanthrenesulfonic acids with ] <ref>], Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) .</ref>		* ] to 2 and 3-phenanthrenesulfonic acids with ]<ref>], Coll. Vol.&nbsp;2, (1943); Vol.&nbsp;16, p.&nbsp;63 (1936).</ref>
	* ] to diphenylaldehyde <ref>], Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) .</ref>		* ] to diphenylaldehyde<ref>], Coll. Vol.&nbsp;5, (1973); Vol.&nbsp;41, p.&nbsp;41 (1961).</ref>
			==Productions==
	===Canonical forms===
			Phenanthrene is extracted from coal tar, where it comprises 5% by weight.<ref name=Ullmann/>
			In principle it could be obtained by chemical synthesis. The '''Bardhan–Sengupta phenanthrene synthesis''' is a classic way to make phenanthrenes.<ref>{{cite book |year= 2010 |chapter= Bardhan Sengupta Synthesis |title= Comprehensive Organic Name Reactions and Reagents |volume= 49 |pages= 215–219 |doi= 10.1002/9780470638859.conrr049 |isbn= 9780470638859 }}</ref>
	Phenanthrene is more stable than its linear isomer ]. A classic and well established explanation is based on ]. A novel theory invokes so-called stabilizing ]s between the C4 and C5 hydrogen atoms.
			:]
			This process involves ] using a tethered ] group using ], which closes the central ring onto an existing aromatic ring. ] using ] ] the other rings into aromatic ones as well. The aromatization of six-membered rings produces ].
	==Natural occurrence==
	Ravatite is a natural analog of synthetic phenanthrene. It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
			Phenanthrene can also be obtained photochemically from certain ]s (]):]
	==References==
			Other synthesis routes include the ] and the ]-type ], as depicted below: ]Commercially phenanthrene is not synthesized but extracted from the byproducts of coal coking, since it makes around 4–6% of ] coal tar.<ref>{{Cite journal |last=Ma |first=Zhi-Hao |last2=Wei |first2=Xian-Yong |last3=Liu |first3=Guang-Hui |last4=Liu |first4=Fang-Jing |last5=Zong |first5=Zhi-Min |date=2021-05-15 |title=Value-added utilization of high-temperature coal tar: A review |url=https://www.sciencedirect.com/science/article/abs/pii/S0016236120329501 |journal=Fuel |volume=292 |pages=119954 |doi=10.1016/j.fuel.2020.119954 |issn=0016-2361}}</ref>
			== Natural occurrences of the phenanthrene derivatives==
			]
			] is the ] found in several ]s, consisting of ] ]s, ]s, and ] ]s, among others. Examples ], ], and ] (DXM).<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a13_227.pub3 |chapter=Hydrocarbons |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2014 |last1=Schmidt |first1=Roland |last2=Griesbaum |first2=Karl |last3=Behr |first3=Arno |last4=Biedenkapp |first4=Dieter |last5=Voges |first5=Heinz-Werner |last6=Garbe |first6=Dorothea |last7=Paetz |first7=Christian |last8=Collin |first8=Gerd |last9=Mayer |first9=Dieter |last10=Höke |first10=Hartmut |pages=1–74 |isbn=978-3-527-30673-2 }}</ref>
			] is a natural mineral consisting of phenanthrene.<ref></ref> It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
			=== In plants ===
			{{Main article|Phenanthrenes}}Phenanthrene derivatives occur in plants as ]. They have been reported from flowering plants, mainly in the family ], and a few in the families ], ] and ], as well as in the lower plant class ] (liverworts).<ref name="Kovacs">{{cite journal |last1=Kovács |first1=Adriána |last2=Vasas |first2=Andrea |last3=Hohmann |first3=Judit |year=2008 |title=Natural phenanthrenes and their biological activity |journal=Phytochemistry |volume=69 |issue=5 |pages=1084–1110 |bibcode=2008PChem..69.1084K |doi=10.1016/j.phytochem.2007.12.005 |pmid=18243254}}</ref>
			==See also==
			* ]
			* ]
			* ]
			== References ==
	{{reflist}}		{{reflist}}
	==External links==		== External links ==
	* at scorecard.org		* at scorecard.org
			{{Hydrocarbons}}
	{{PAHs}}		{{PAHs}}
			{{Organic reactions}}
			{{Authority control}}
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