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Revision as of 06:35, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'ChEBI').← Previous edit		Latest revision as of 19:30, 19 January 2025 edit undoBernanke's Crossbow (talk | contribs)Extended confirmed users7,929 edits →See also: dibenzothiophene
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	{{distinguish|fluorine}}		{{distinguish|Hydrogen fluoride{{!}}Fluorane|Fluorine|Fluorone|Fluorenone}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 415490306		| verifiedrevid = 443822810
	| Reference = <ref>'']'', 11th Edition, '''4081'''</ref>		| Reference = <ref>'']'', 11th Edition, '''4081'''</ref>
	| Name = Fluorene
	| ImageFile_Ref = {{chemboximage|correct|??}}		| Name = Fluorene
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Fluoreen genummerd.png		| ImageFile = Fluorene.svg
			| ImageClass = skin-invert-image
	| ImageSize = 200px
	| ImageName =		| ImageSize =
	| ImageFile1 = Fluorene-from-xtal-3D-balls.png		| ImageName =
			| ImageFile1 = Fluorene-from-xtal-3D-balls.png
	| ImageFile2 = Fluorene-3D-vdW.png		| ImageFile2 = Fluorene-3D-vdW.png
			| ImageClass2 = bg-transparent
	| IUPACName = 9''H''-Fluorene
			| PIN = 9''H''-Fluorene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=207 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
⚫	| Section1 = {{Chembox Identifiers
			| SystematicName = Tricyclotrideca-2,4,6,9,11,13-hexaene
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	|Section1={{Chembox Identifiers
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6592		| ChemSpiderID = 6592
	| PubChem = 6853		| PubChem = 6853
			| RTECS = LL5670000
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C07715		| KEGG = C07715
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	| StdInChIKey = NIHNNTQXNPWCJQ-UHFFFAOYSA-N		| StdInChIKey = NIHNNTQXNPWCJQ-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 86-73-7		| CASNo = 86-73-7
	| EINECS = 201-695-5		| EINECS = 201-695-5
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 3Q2UY0968A		| UNII = 3Q2UY0968A
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 28266		| ChEBI = 28266
	| SMILES = c1ccc-2c(c1)Cc3c2cccc3		| SMILES = c1ccc2c3ccccc3Cc2c1
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=13|H=10
	| Formula = C<sub>13</sub>H<sub>10</sub>
			| MeltingPtC = 116 to 117
	| MolarMass = 166.223 g/mol
			| MeltingPt_notes =
	| MeltingPt = 116-117 °C
	| BoilingPtC = 295		| BoilingPtC = 295
	| Density = 1.202 g/mL		| Density = 1.202 g/mL
	| pKa = 22.6		| Solubility = 1.992 mg/L
			| SolubleOther = organic solvents
			| pKa = 22.6
			| LogP = 4.18
			| MagSus = -110.5·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section3 = {{Chembox Hazards		|Section7={{Chembox Hazards
			| ExternalSDS =
⚫	| NFPA-H = 1
	| NFPA-F = 1		| NFPA-H = 1
	| NFPA-R = 0		| NFPA-F = 1
	| NFPA-O =		| NFPA-R = 0
		⚫	| NFPA-S =
			| FlashPtC = 152
			| LD50 = 16000 mg/kg (oral, rat)
	}}		}}
	}}		}}
	'''Fluorene''', or '''9''H''-fluorene''', is a ]. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of ]. It is combustible. It has a violet ], hence its name. For commercial purposes it is obtained from ]. It is insoluble in water and soluble in ] and ].		'''Fluorene''' {{IPAc-en|ˈ|f|l|ʊər|iː|n}}, or '''9''H''-fluorene''' is an ] with the formula (C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CH<sub>2</sub>. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of ]. Despite its name, it does not contain the element ], but rather it comes from the violet ] it exhibits. For commercial purposes it is obtained from ],<ref name=Ullmanns/> where it was discovered and named by ] in 1867.<ref>{{Cite book |url=https://books.google.com/books?id=lLZJAQAAMAAJ&pg=PA222 |title=Annales de chimie et de physique |date=1867 |publisher=Masson. |language=fr}}</ref>
			It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a ], the five-membered ring has no aromatic properties.{{citation needed|date=October 2023}} Fluorene is mildly acidic.
	==Synthesis, structure, and reactivity==		==Synthesis, structure, and reactivity==
			Although fluorene is obtained from coal tar, it can also be prepared by dehydrogenation of ].<ref name=Ullmanns>{{Ullmann|doi=10.1002/14356007.a13_227|title=Hydrocarbons|year=2000|last1=Griesbaum|first1=Karl|last2=Behr|first2=Arno|last3=Biedenkapp|first3=Dieter|last4=Voges|first4=Heinz-Werner|last5=Garbe|first5=Dorothea|last6=Paetz|first6=Christian|last7=Collin|first7=Gerd|last8=Mayer|first8=Dieter|last9=Höke|first9=Hartmut|isbn=3527306730}}</ref> Alternatively, it can be prepared by the reduction of ] with ]<ref>Fittig, Rud. (1873), "Ueber einen neuen Kohlenwasserstoff aus dem Diphenylenketon" Ber. Dtsch. Chem. Ges. volume 6, p. 187.{{doi|10.1002/cber.18730060169}}</ref> or ]–].<ref>{{cite journal | last1=Hicks | first1=Latorya D. | last2=Han | first2=Ja Kyung | last3=Fry | first3=Albert J. | title=Hypophosphorous acid–iodine: a novel reducing system. | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=41 | issue=41 | year=2000 | issn=0040-4039 | doi=10.1016/s0040-4039(00)01359-9 | pages=7817–7820}}</ref> The fluorene molecule is nearly planar,<ref name=burns>D. M. Burns, ] (1954), ''Molecular Structure of Fluorene'' Nature volume 173, p. 635. {{doi|10.1038/173635a0}}</ref> although each of the two benzene rings is coplanar with the central carbon 9.<ref>{{cite journal |doi=10.1107/S0108270184009963|title=Structure of fluorene, C13H10, at 159 K|year=1984|last1=Gerkin|first1=R. E.|last2=Lundstedt|first2=A. P.|last3=Reppart|first3=W. J.|journal=Acta Crystallographica Section C Crystal Structure Communications|volume=40|issue=11|pages=1892–1894|bibcode=1984AcCrC..40.1892G }}</ref>
	Although fluorene is obtained from coal tar, it can also be prepared by dehydrogenation of ].<ref name=Ullmanns>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}}</ref>
			Fluorene can be found after the ] of ] such as ], ] and ].<ref>{{Cite journal|last1=Wang|first1=Zhenlei|last2=Richter|first2=Henning|last3=Howard|first3=Jack B.|last4=Jordan|first4=Jude|last5=Carlson|first5=Joel|last6=Levendis|first6=Yiannis A.|date=2004-06-01|title=Laboratory Investigation of the Products of the Incomplete Combustion of Waste Plastics and Techniques for Their Minimization|url=https://doi.org/10.1021/ie030477u|journal=Industrial & Engineering Chemistry Research|volume=43|issue=12|pages=2873–2886|doi=10.1021/ie030477u|issn=0888-5885}}</ref>
	The fluorene molecule is nearly planar,<ref name=burns>
	D. M. Burns, John Iball (1954), ''Molecular Structure of Fluorene'' Nature volume 173, p. 635. {{doi|10.1038/173635a0}}</ref> although each of the two benzene rings is coplanar with the central carbon 9.<ref name=gerkin> R. E. Gerkin, A. P. Lundstedt and W. J. Reppart (1984) ''Structure of fluorene, C<sub>13</sub>H<sub>10</sub>, at 159 K'' Acta Crystallographica, volume C40, pp. 1892–1894 {{doi|10.1107/S0108270184009963}}</ref>
	===Acidity===		===Acidity===
	The C9-H sites of the fluorene ring are weakly acidic (] = 22.6 in ].<ref>{{cite journal | title = Equilibrium acidities in dimethyl sulfoxide solution | author = F. G. Bordwell | journal = Acc. Chem. Res. | volume = 21 | year = 1988 | pages = 456–463 | doi = 10.1021/ar00156a004}}		The C9-H sites of the fluorene ring are weakly acidic (] = 22.6 in ].<ref>{{cite journal | title = Equilibrium acidities in dimethyl sulfoxide solution | author = F. G. Bordwell | journal = Acc. Chem. Res. | volume = 21 | year = 1988 | pages = 456–463 | doi = 10.1021/ar00156a004 | issue = 12}}</ref>) Deprotonation gives the stable '''fluorenyl''' anion, nominally C<sub>13</sub>H<sub>9</sub><sup>&minus;</sup>, which is ] and has an intense orange colour. The anion is a ]. ]s react with it by adding to the 9-position. The purification of fluorene exploits its acidity and the low solubility of its sodium derivative in hydrocarbon solvents.
	</ref>) Deprotonation gives the stable ] "anion", nominally C<sub>13</sub>H<sub>9</sub><sup>&minus;</sup>, which is ] and has an intense orange colour. The anion is a ], and most ]s react with it by adding to the 9-position. The purification of fluorene exploits its acidity and the low solubility of its sodium derivative in hydrocarbon solvents.
	Both protons can be removed from C9. For example, ] can be obtained by treating fluorene with ] metal in boiling ].<ref name=scherf>G. W. Scherf and R. K. Brown (1960), ''''. Canadian Journal of Chemistry, Vol. 38, p. 697.</ref>		Both protons can be removed from C9. For example, 9,9-fluorenyldipotassium can be obtained by treating fluorene with ] metal in boiling ].<ref name=scherf>{{cite journal|author1=G. W. Scherf|author2=R. K. Brown|year=1960|title=Potassium Derivatives of Fluorene as Intermediates in the Preparation of C9-substituted Fluorenes. I. The Preparation of 9-fluorenyl Potassium and the Infrared Spectra of Fluorene and Some C9-substituted Fluorenes|journal=Canadian Journal of Chemistry|volume=38|page=697|doi=10.1139/v60-100}}.</ref>
			===Ligand properties===
			Fluorene and its derivatives can be deprotonated to give ]s akin to ].
			] for producing ] ].<ref>{{cite journal|author1=Ewen, J. A.|author2=Jones, R. L.|author3=Razavi, A.|author4=Ferrara, J. D.|title=Syndiospecific Propylene Polymerizations with Group IVB Metallocenes|journal=Journal of the American Chemical Society|year=1988|volume=110|issue=18|pages=6255–6256|doi=10.1021/ja00226a056|pmid=22148816}}</ref>]]
	==Uses==		==Uses==
	Fluorene is a precursor to other fluorene compounds; the parent species has few applications. Fluorene-9-carboxylic acid is a precursor to pharmaceuticals. 2-Aminofluorene, 3,6-bis-(dimethylaminofluorene), and 2,7-diiodofluorene are precursors to dyes. Oxidation of fluorene gives fluorenone, which is nitrated to give commercially useful derivatives. ] (Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc) ] on amines in ].<ref name=Ullmanns/>		Fluorene is a precursor to other fluorene compounds; the parent species has few applications. Fluorene-9-carboxylic acid is a precursor to pharmaceuticals. Oxidation of fluorene gives ], which is nitrated to give commercially useful derivatives. ] (Fmoc chloride) is used to introduce the 9-fluorenylmethyl carbamate (Fmoc) ] on amines in ].<ref name=Ullmanns/>
	] polymers (where carbon 7 of one unit is linked to carbon 2 of the next one, displacing two hydrogens) are ] and ], and have been much investigated for use as a ] in ]s.		] polymers (where carbon 7 of one unit is linked to carbon 2 of the next one, displacing two hydrogens) are ] and ], and have been much investigated as a ] in ]s.
			===Fluorene dyes===
			Fluorene dyes are well developed. Most are prepared by condensation of the active methylene group with carbonyls. 2-Aminofluorene, 3,6-bis-(dimethylamino)fluorene, and 2,7-diiodofluorene are precursors to dyes.<ref>{{cite journal|title=Organic dyes based on fluorene and its derivatives|author1=Kurdyukova, I. V. |author2=Ishchenko, A. A. |journal=Russian Chemical Reviews|year=2012|volume=81|issue=3|pages=258–290|doi=10.1070/RC2012v081n03ABEH004211|bibcode=2012RuCRv..81..258K|s2cid=95312830 }}</ref>
			==See also==
			*]
			*]
			*]
			*]
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	==References==		==References==
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	==External links==		==External links==
	*
	* in the National Institute of Standards and Technology database.		* in the National Institute of Standards and Technology database.
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