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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 413078361		| verifiedrevid = 443823513
	| Name = Fluorobenzene		| Name = Fluorobenzene
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileL1 = Fluorobenzene-2D-skeletal.png		| ImageFileL1 = Fluorobenzene-2D-skeletal.png
	| ImageSizeL1 = 80px		| ImageSizeL1 = 80px
Line 8:		Line 10:
	| ImageSizeR1 = 120px		| ImageSizeR1 = 120px
	| ImageNameR1 = Space-filling model of fluorobenzene		| ImageNameR1 = Space-filling model of fluorobenzene
	| IUPACName = Fluorobenzene		| PIN = Fluorobenzene
	| OtherNames = Phenyl fluoride<br />Monofluorobenzene		| OtherNames = Phenyl fluoride<br />Monofluorobenzene
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| CASNo = 462-06-6
			| Beilstein = 1236623
		⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEBI = 5115
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEMBL = 16070
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 9614		| ChemSpiderID = 9614
	| PubChem = 10008		| EC_number = 207-321-7
			| Gmelin = 49856
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C11272		| KEGG = C11272
			| PubChem = 10008
			| UNNumber = 2387
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = G3TSZ68K12
	| InChI = 1/C6H5F/c7-6-4-2-1-3-5-6/h1-5H		| InChI = 1/C6H5F/c7-6-4-2-1-3-5-6/h1-5H
⚫	| ChEBI = 5115
⚫	| SMILES = Fc1ccccc1
	| InChIKey = PYLWMHQQBFSUBP-UHFFFAOYAM		| InChIKey = PYLWMHQQBFSUBP-UHFFFAOYAM
⚫	| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫	| ChEMBL = 16070
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H		| StdInChI = 1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = PYLWMHQQBFSUBP-UHFFFAOYSA-N		| StdInChIKey = PYLWMHQQBFSUBP-UHFFFAOYSA-N
		⚫	| SMILES = Fc1ccccc1
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| CASNo = 462-06-6
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>6</sub>H<sub>5</sub>F		| Formula = C<sub>6</sub>H<sub>5</sub>F
	| MolarMass = 96.103		| MolarMass = 96.103
	| Appearance = Colorless liquid		| Appearance = Colorless liquid
	| Density = 1.025 g/mL, liquid		| Density = 1.025 g/mL, liquid
	| Solubility = low		| Solubility = low
			| MeltingPtC = −44
	| MeltingPt = −40 °C
			| BoilingPtC = 84 to 85
	| BoilingPt = 84–85 °C
			| BoilingPt_notes =
			| MagSus = -58.4·10<sup>−6</sup> cm<sup>3</sup>/mol
			| RefractIndex = 1.46553
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| MolShape = Planar		| MolShape = Planar
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| NFPA-H = 1		| NFPA-H = 1
	| NFPA-F = 3		| NFPA-F = 3
	| NFPA-R = 0		| NFPA-R = 0
			| Hazards_ref=
	| RPhrases = {{R36}}, {{R37}}, {{R38}}
	| SPhrases = {{S16}}, {{S26}}, {{S36}}		| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|225|318|411}}
			| PPhrases = {{P-phrases|210|233|240|241|242|243|264|273|280|303+361+353|305+351+338|310|337+313|370+378|391|403+235|501}}
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherFunctn = ]<br />]<br />]		| OtherFunction = ]<br />]<br />]
	| Function = halobenzenes		| OtherFunction_label = halobenzenes
	| OtherCpds = ]<br>]		| OtherCompounds = ]<br>]
	}}		}}
	}}		}}
	'''Fluorobenzene''' is the ] with the formula C<sub>6</sub>H<sub>5</sub>F, often abbreviated ]F. This species is a ] of ], with a single ] atom attached. Its melting point is 44&nbsp;°C lower than that of benzene, indicative of the remarkable effect of fluorination on the intermolecular interactions as seen throughout ]. In contrast, the boiling points of PhF and benzene differ by only 4&nbsp;°C.		'''Fluorobenzene''' is an ] and the simplest of the ], with the formula C<sub>6</sub>H<sub>5</sub>F, often abbreviated ]F. A colorless liquid, it is a precursor to many fluorophenyl compounds.
	== Preparation ==		==Preparation==
		⚫	PhF was first reported in 1886 by O. Wallach at the ], who prepared the compound in two steps. ] chloride was first converted to a ] using piperidine:
⚫	On the laboratory scale, PhF is conveniently prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate<ref>{{OrgSynth|author = Flood, D. T.|year = 1943|title=Fluorobenzene|collvol = 2|collvolpages = 295|prep= CV2P0295}}.</ref>
	:PhN<sub>2</sub>BF<sub>4</sub> &rarr; PhF + ] + ]		:Cl + 2 (CH<sub>2</sub>)<sub>5</sub>NH → PhN=N-N(CH<sub>2</sub>)<sub>5</sub> + Cl
			The triazine was then cleaved with ]:
		⚫	:PhN=N-N(CH<sub>2</sub>)<sub>5</sub> + 2 HF → PhF + N<sub>2</sub> + F
		⚫	Historical note: in Wallach's era, the element fluorine was symbolized with "Fl". Thus, his procedure is subtitled "Fluorbenzol, C<sub>6</sub>H<sub>5</sub>Fl".<ref>{{cite journal | doi = 10.1002/jlac.18862350303 | title = Ueber einen Weg zur leichten Gewinnung organischer Fluorverbindungen | date = 1886 | last1 = Demselben | journal = Justus Liebigs Annalen der Chemie | volume = 235 | issue = 3 | pages = 255–271 }}</ref>
⚫	According to the procedure, solid BF<sub>4</sub> is heated with a flame to initiate an ] that affords two volatile products, PhF and BF<sub>3</sub>, which are readily separated because of their differing ]s.
		⚫	On the laboratory scale, PhF is prepared by the ] of the ] tetrafluoroborate:
⚫	PhF was first reported in 1886 by O. Wallach at the ], who prepared the compound in two steps, starting also with a phenyldiazonium salt. The diazonium chloride was first converted to its piperidinide, which in turn was cloven using ].
			:PhN<sub>2</sub>BF<sub>4</sub> → PhF + BF<sub>3</sub> + N<sub>2</sub>
		⚫	According to the procedure, solid BF<sub>4</sub> is heated with a flame to initiate an ], which also affords ] and nitrogen gas. Product PhF and BF<sub>3</sub> are readily separated because of their differing ]s.<ref>{{cite journal|author = Flood, D. T.|year = 1933|title=Fluorobenzene|volume=13|page=46|journal=Org. Synth. |doi=10.15227/orgsyn.013.0046}}.</ref>
		⚫	The technical synthesis is by the reaction of ] with ]. The initially formed ] undergoes a ring expansion and subsequent elimination of ].
	:Cl + 2 C<sub>5</sub>H<sub>10</sub>NH &rarr; PhN=N-NC<sub>5</sub>H<sub>10</sub> + Cl
			==Reactions==
⚫	:PhN=N-NC<sub>5</sub>H<sub>10</sub> + 2 HF &rarr; PhF + N<sub>2</sub> + F
			PhF behaves rather differently from other halobenzene derivatives owing to the pi-donor properties of fluoride. For example, the para position is more activated than benzene toward electrophiles. For this reason, it can be converted to 1-bromo-4-fluorobenzene with relatively high efficiency.<ref>{{cite journal|title=The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena|first1=Joel|last1=Rosenthal|first2=David I.|last2=Schuster|journal=J. Chem. Educ.|year=2003|volume=80|issue=6|page= 679|doi=10.1021/ed080p679|bibcode=2003JChEd..80..679R}}</ref>
			==Solvent properties==
⚫	An interesting historical note: in Wallach’s era, the element fluorine was symbolized with “Fl”. Thus, his procedure is subtitled “Fluorbenzol, C<sub>6</sub>H<sub>5</sub>Fl”.<ref>Wallach, O. “Über einen Weg zur leichten Gewinnung organischer Fluorverbindungen” (Concerning a method for easily preparing organic fluorine compounds) Justus Liebig's Annalen der Chemie, 1886, Volume 235, p.&nbsp;255–271; {{doi|10.1002/jlac.18862350303}}</ref>
		⚫	:<sup>+</sup>, a coordination complex of fluorobenzene.]]
			PhF is a useful solvent for highly reactive species. Its melting point at -44&nbsp;°C is lower than that of benzene. In contrast, the boiling points of PhF and benzene are very similar, differing by only 4&nbsp;°C. It is considerably more polar than benzene, with a dielectric constant of 5.42 compared to 2.28 for benzene at 298 K.<ref>{{Cite book|title=Table of Dielectric Constants of Pure Liquids|publisher=National Bureau of Standards|year=1951}}</ref> Fluorobenzene is a relatively inert compound reflecting the strength of the C–F bond.
			Although it is usually considered a non-coordinating solvent, a metal complex of PhF has been crystallized.<ref>{{cite book | doi = 10.1016/B0-08-045047-4/00028-5 | chapter = Transition Metal-mediated C–F Bond Activation | title = Comprehensive Organometallic Chemistry III | date = 2007 | last1 = Perutz | first1 = R.N. | last2 = Braun | first2 = T. | pages = 725–758 | isbn = 978-0-08-045047-6 }}</ref>
⚫	The technical synthesis is by the reaction of ] with ]. The initially formed cyclopropane undergoes a ring expansion and subsequent elimination of ].
	== Reactions ==		==See also==
			*]
	PhF is a relatively inert compound because the C–F bond is very strong. PhF is a useful solvent for highly reactive species, but a metal complex has been crystallized.<ref>R.N. Perutz and T. Braun “Transition Metal-mediated C–F Bond Activation” Comprehensive Organometallic Chemistry III, 2007, Volume 1, p.&nbsp;725–758; {{doi|10.1016/B0-08-045047-4/00028-5}}.</ref>
			*]
⚫	:<sup>+</sup>, a coordination complex of fluorobenzene.]]
			*]
	Fluorination of fluorobenzene gives mainly ].
	== References ==		==References==
	{{reflist}}		{{reflist}}
			{{fluorine compounds}}
	]		]
	]		]
	]
	]
	]
	]
	]