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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 411791150
			| Watchedfields = changed
⚫	|ImageFileL1=F-TEDA-BF4.svg
		⚫	| verifiedrevid = 443880836
	|ImageSizeL1=100px
		⚫	| ImageFileL1=F-TEDA-BF4.svg
⚫	|ImageFileR1=Selectfluor-from-xtal-3D-balls.png
	|ImageSizeR1=100px		| ImageSizeL1=100px
		⚫	| ImageFileR1=Selectfluor-from-xtal-3D-balls.png
⚫	|IUPACName=1-(chloromethyl)-4-fluoro-1,4-diazo<br/>niabicyclooctane ditetrafluoroborate
			| ImageSizeR1=100px
⚫	|OtherNames=F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)
		⚫	| IUPACName=1-(Chloromethyl)-4-fluoro-1,4-diazabicyclooctane-1,4-diium ditetrafluoroborate
		⚫	| OtherNames=F-TEDA, N-Chloromethyl-N-fluorotriethylenediammonium bis(tetrafluoroborate)<br/>1-Chloromethyl-4-fluoro-1,4-diazoniabicyclooctane bis(tetrafluoroborate)
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo=140681-55-6		| CASNo=140681-55-6
⚫	| PubChem= 2724933
			| EINECS = 414-380-4
	| SMILES=
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 2007047
		⚫	| PubChem= 2724933
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 4P1ZA6R76D
			| InChI = 1/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1
			| InChIKey = TXRPHPUGYLSHCX-UHFFFAOYAI
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = TXRPHPUGYLSHCX-UHFFFAOYSA-N
			| SMILES = (F)(F)(F)F.(F)(F)(F)F.C1C2(CC1(CC2)CCl)F
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>7</sub>H<sub>14</sub>B<sub>2</sub>ClF<sub>9</sub>N<sub>2</sub>		| Formula=C<sub>7</sub>H<sub>14</sub>B<sub>2</sub>ClF<sub>9</sub>N<sub>2</sub>
	| MolarMass=354.26 g/mol		| MolarMass=354.26 g/mol
	| Appearance=colourless solid		| Appearance=colourless solid
	| Density=		| Density=
			| MeltingPtC=190
	| MeltingPt=234
			| MeltingPt_notes= decomposes >80 °C, exact m.p. is uncertain<ref name=eEROS/>
	| BoilingPt=
	| Solubility=		| BoilingPt=
			| Solubility=
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
	'''1-Chloromethyl-4-fluoro-1,4-diazoniabicyclooctane bis(tetrafluoroborate)''' or '''Selectfluor® ''', a trademark of ], is a ] in ] that is used as a ] donor. This compound is a derivative of the ] ]® . This colourless salt was first described in 1992<ref>{{cite journal| doi = 10.1039/C39920000595| title = 1-Alkyl-4-fluoro-1,4-diazoniabicyclooctane salts: a novel family of electrophilic fluorinating agents| year = 1992| author = Banks, R. Eric| journal = Journal of the Chemical Society Chemical Communications| pages = 595| last2 = Mohialdin-Khaffaf| first2 = Suad N.| last3 = Lal| first3 = G. Sankar| last4 = Sharif| first4 = Iqbal| last5 = Syvret| first5 = Robert G.| issue = 8}}</ref> and has since been commercialized for use in ].		'''Selectfluor''', a trademark of ], is a ] in ] that is used as a ] donor. This compound is a derivative of the nucleophillic base ]. It is a colourless salt that tolerates air and even water. It has been commercialized for use for ].<ref name=eEROS>{{cite book |doi=10.1002/047084289X.rc116.pub2|chapter=1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo&#91;2.2.2&#93;octane Bis(tetrafluoroborate)|title=Encyclopedia of Reagents for Organic Synthesis|year=2007|last1=Banks|first1=R. Eric|last2=Murtagh|first2=Vincent|last3=An|first3=Ilhwan|last4=Maleczka|first4=Robert E.|isbn=978-0471936237}}</ref>
	==Preparation==		==Preparation==
		⚫	:]
	Selectfluor® reagent is commercially available. It is synthesized by the ] of diazabicyclooctane (DABCO® ) with ], followed by ] with ] (replacing the chloride ] for the tetrafluoroborate). Finally, this salt is treated with elemental fluorine and sodium tetrafluoroborate:<ref>{{cite journal | doi = 10.1039/C39920000595 | title = 1-Alkyl-4-fluoro-1,4-diazoniabicyclooctane salts: a novel family of electrophilic fluorinating agents | year = 1992 | author = Banks, R. Eric et. al. | journal = J. Chem. Soc., Chem. Commun. | issue = 8 | pages = 595–596}}</ref>		Selectfluor is synthesized by the ''N''-] of octane (DABCO)]] with ] in a ], followed by ] with ] (replacing the chloride ] for the tetrafluoroborate). The resulting salt is treated with elemental fluorine and sodium tetrafluoroborate:<ref name=Angew/>
			The cation is often depicted with one skewed ethylene ((CH<sub>2</sub>)<sub>2</sub>) group. In fact, these pairs of CH<sub>2</sub> groups are eclipsed so that the cation has idealized C<sub>3h</sub> ].
⚫	:]
			==Mechanism of fluorination==
			Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an ] attack at fluorine. This distinction has not been decided.<ref name=Angew>{{cite journal|doi=10.1002/anie.200400648|title=Selectfluor: Mechanistic Insight and Applications|year=2005|last1=Nyffeler|first1=Paul T.|last2=Durón|first2=Sergio Gonzalez|last3=Burkart|first3=Michael D.|last4=Vincent|first4=Stéphane P.|last5=Wong|first5=Chi-Huey|journal=Angewandte Chemie International Edition|volume=44|issue=2|pages=192–212|pmid=15578736|doi-access=free}}</ref> By using a charge-spin separated probe,<ref name="TojoMorishima1995">{{cite journal|last1=Tojo|first1=Sachiko|last2=Morishima|first2=Kazuhiro|last3=Ishida|first3=Akito|last4=Majima|first4=Tetsuro|last5=Takamuku|first5=Setsuo|title=Remarkable Enhancements of Isomerization and Oxidation of Radical Cations of Stilbene Derivatives Induced by Charge-Spin Separation|journal=The Journal of Organic Chemistry|volume=60|issue=15|year=1995|pages=4684–4685|issn=0022-3263|doi=10.1021/jo00120a004}}</ref> it was possible to show that the electrophilic fluorination of stilbenes with Selectfluor proceeds through an SET/fluorine atom transfer mechanism.<ref name="BrandtLee2014">{{cite journal|last1=Brandt|first1=Jochen R.|last2=Lee|first2=Eunsung|last3=Boursalian|first3=Gregory B.|last4=Ritter|first4=Tobias|title=Mechanism of electrophilic fluorination with Pd(iv): fluoride capture and subsequent oxidative fluoride transfer|journal= Chem. Sci.|volume=5|issue=1|year=2014|pages=169–179|issn=2041-6520|doi=10.1039/C3SC52367E|pmc=3870902|pmid=24376910}}</ref>
			In certain cases Selectfluor can ].<ref>{{Cite journal|title = Recent advances in radical fluorination|journal = ]|year = 2015|pages = 2554–2569|volume = 47|issue = 17|doi = 10.1055/s-0034-1378824|first1 = J.-F.|last1 = Paquin|first2 = G.|last2 = Sammis|first3 = C.|last3 = Chatalova-Sazepin|first4 = R.|last4 = Hemelaere| s2cid=196807570 }}</ref>
	==Applications==		==Applications==
	The conventional source of "electrophilic fluorine," i.e. the equivalent to the ] F<sup>+</sup>, is gaseous fluorine, which requires specialised equipment for manipulation. Selectfluor® reagent is a salt that requires only routine procedures for its use. Like F<sub>2</sub>, the salt delivers the equivalent of F<sup>+</sup>. It is mainly used in the synthesis of ]s:<ref>{{cite journal | doi = 10.1055/s-2006-933124 | title = Selectfluor® (F-TEDA-BF<sub>4</sub>) C<sub>7</sub>H<sub>14</sub>B<sub>2</sub>ClF<sub>9</sub>N<sub>2</sub> | year = 2006 | author = Manral, Laxmi | journal = Synlett | pages = 0807 | issue = 5}}</ref><ref>{{cite journal | author = Stojan Stavbera and Marko Zupana | year = 2005		The conventional source of "electrophilic fluorine", i.e. the equivalent to the ] F<sup>+</sup>, is gaseous fluorine, which requires specialised equipment for manipulation. Selectfluor reagent is a salt, the use of which requires only routine procedures. Like F<sub>2</sub>, the salt delivers the equivalent of F<sup>+</sup>. It is mainly used in the synthesis of ]s:<ref name=Angew/>
	| title = Selectfluortm F-TEDA-BF4 As a Versatile Mediator or Catalyst in Organic Chemistry | journal = Acta Chim. Slov. | volume = 52| pages = 13–26 | url = http://acta.chem-soc.si/52/52-1-13.pdf}}</ref><ref>{{cite journal | last1 = Singh | first1 = R.P. | last2 = Shreeve | first2 = J. M. | year = 2004 | title = Recent Highlights in Electrophilic Fluorination with 1-Chloromethyl-4-Fluoro-1,4-DiazoniabicycloOctane Bis(Tetrafluoroborate) | volume = 37 | issue = 1 | pages = 31–44 | journal = ] | doi = 10.1021/ar030043v | pmid=14730992}}</ref>
	]		]
	===Specialized applications===		===Specialized applications===
	Selectfluor® reagent also serves as a strong oxidant, a property that is useful in other reactions in ]. ] of ]s and ]. As applied to ], Selectfluor® reagent activates I<sub>2</sub> bond.		Selectfluor reagent also serves as a strong oxidant, a property that is useful in other reactions in ]. ] of ]s and ]. As applied to ], Selectfluor reagent activates the I–I bond in I<sub>2</sub> molecule.<ref>{{Cite journal|last1=Stavber|first1=Stojan|last2=Kralj|first2=Petra|last3=Zupan|first3=Marko|date=2002-08-01|title=Progressive Direct Iodination of Sterically Hindered Alkyl Substituted Benzenes|journal=Synthesis|language=en|volume=2002|issue=11|pages=1513–1518|doi=10.1055/s-2002-33339|issn=0039-7881}}</ref>
			==Related reagents==
			Similar to Selectfluor are ''N''-fluorosulfonimides:<ref name=OR>{{cite book|doi=10.1002/0471264180.or069.02 |chapter=Electrophilic Fluorination with N–F Reagents |title=Organic Reactions |date=2008 |last1=Baudoux |first1=Jérôme |last2=Cahard |first2=Dominique |pages=1–326 |isbn=978-0-471-26418-7 }}</ref>
			]
	==References==		==References==
	{{Reflist}}		{{Reflist}}
	==Other References==
	# Lal, G. S., J. Org. Chem. 1993, 58, 2791.
	# Lal, G. S., Synth. Commun. 1995, 25 (5), 725
	# Banks, R. E.; Lawrence, N. J.; Popplewell, A. L., J. Chem. Soc., Chem. Commun. 1994, 343.
	# Zupan, M.; Iskra, J.; Stavber, S., J. Fluorine Chem., 1995, 70, 7.
	# Matthews, D.P.; Miller, S. C.; Jarvi E. T.; Sabol, J. S.; McCarthy, J. R., Tettrahedron Lett. 1993, 34 (19), 3057.
	# Brunaus, M.; Dell, C. P.; Owton, W. M., J. Fluorine Chem. 1994, 201.
	# McClinton, M. A. ; Sik, V., J. Chem. Soc., Perkin Trans. I, 1992, 1891.
	# Hodson, H. F.; Madge, D. J.; Slawin, A. N. Z.; Widdawson, D. A.; Williams, D. J., Tetrahedron, 1994, 50 (6), 1899.
	# Stavber, S.; Zupan, M., J. Chem. Soc., Chem. Commun. 1994, 149.
	# Stavber, S.; Sotler, J.; Zupan, M., Tettrahedron Lett. 1994, 35 (7), 1105.
	== Patents ==		== Patents ==
	* {{patent|US|5459267|"1-substituted-4-fluoro-1,4-diazoniabicyclooctane salts and their application as fluorinating agents"}}		* {{patent|US|5459267|"1-substituted-4-fluoro-1,4-diazoniabicyclooctane salts and their application as fluorinating agents"}}
⚫	]
⚫	]
	]
	* {{patent|US|55227493|"Fluorinated Sulfonamide Derivatives"}}		* {{patent|US|55227493|"Fluorinated Sulfonamide Derivatives"}}
	* {{patent|US|5086178|"Fluorinated Diazabicycloalkane Derivatives"}}		* {{patent|US|5086178|"Fluorinated Diazabicycloalkane Derivatives"}}
	* {{patent|US|5473065|"Fluorinated Diazabicycloalkane Derivatives"}}		* {{patent|US|5473065|"Fluorinated Diazabicycloalkane Derivatives"}}
		⚫	* {{patent|US|5442084|"Method of Selective Fluorination"}}
			{{Tetrafluoroborates}}
		⚫	]
⚫	* {{patent|US|5442084|"Method of Selective Fluorination"}}
		⚫	]
			]
			]
			]
			]
			]