Selectfluor

Structural formula
General
Surname	Selectfluor
other names	1-chloromethyl-4-fluoro-1,4-diazonia bicyclo [2.2.2] octanebis (tetrafluoroborate); N -chloromethyl- N ′ -fluorotriethylene diammonium bis (tetrafluoroborate); F-TEDA;
Molecular formula	C 7 H 14 B 2 ClF 9 N 2
Brief description	White dust
External identifiers / databases
EC number	414-380-4
ECHA InfoCard	100.101.349
PubChem	2724933
Wikidata	Q2649515
properties
Molar mass	354.26 g mol −1
Physical state	firmly
Melting point	260 ° C
solubility	Easily soluble in water (176 g l −1 at 20 ° C)
safety instructions
H and P phrases	H: 252-302-317-318-412
	P: 235 + 410-273-280-305 + 351 + 338
Toxicological data	640 mg kg −1 ( LD 50 , rat , oral , male)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Selectfluor is a fluorinating reagent and a derivative of DABCO . Selectfluor was first described by Eric Banks and co-workers in 1992 and has been used for electrophilic fluorination ever since. The compound is extremely stable and less toxic than pure fluorine .

different representation

Extraction and presentation

The synthesis of Selectfluor begins with the alkylation of DABCO with dichloromethane . The chloride counterions are then exchanged with sodium tetrafluoroborate . The sodium chloride is precipitated from the acetonitrile solution . The intermediate product is fluorinated with F ₂ in the last step .

use

Selectfluor has a wide range of uses in organofluorochemistry as a source of electrophilic fluorine as well as in radical fluorination .

Individual evidence

↑ ^a ^b Data sheet Selectfluor ^® fluorinating reagent,> 95% in F + active from Sigma-Aldrich , accessed on January 20, 2015 ( PDF ).
↑ ^a ^b ^c Entry on 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo (2.2.2) octane-bis-tetrafluoroborate) in the GESTIS substance database of the IFA , accessed on February 5, 2017(JavaScript required) .
↑ Entry on 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octanbis (tetrafluoroborate) Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 13, 2017. Manufacturers or distributors can use the expand harmonized classification and labeling .
↑ ^a ^b ^c ^d Paul T. Nyffeler, Sergio Gonzalez Durón, Michael D. Burkart, Stéphane P. Vincent, Chi-Huey Wong: Selectfluor: Mechanisms and Applications . In: Angewandte Chemie . tape 117 , no. 2 , January 2005, p. 196-217 , doi : 10.1002 / anie.200400648 .
^ R. Eric Banks, Suad N. Mohialdin-Khaffaf, G. Sankar Lal, Iqbal Sharif, Robert G. Syvret: 1-Alkyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octane salts: a novel family of electrophilic fluorinating agents . In: Journal of the Chemical Society, Chemical Communications . No. 8 , 1992, pp. 595 , doi : 10.1039 / C39920000595 .
↑ Laxmi Manral: Selectfluor (F-TEDA-BF ₄ ) C ₇ H ₁₄ B ₂ ClF ₉ N ₂ . In: Synlett . No. 5 , 2006, p. 0807-0808 , doi : 10.1055 / s-2006-933124 .

[Sigma-1] Data sheet Selectfluor ^® fluorinating reagent,> 95% in F + active from Sigma-Aldrich , accessed on January 20, 2015 ( PDF ).

[GESTIS-2] Entry on 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo (2.2.2) octane-bis-tetrafluoroborate) in the GESTIS substance database of the IFA , accessed on February 5, 2017(JavaScript required) .

[CLP_100.101.349-3] Entry on 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octanbis (tetrafluoroborate) Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 13, 2017. Manufacturers or distributors can use the expand harmonized classification and labeling .

[angewandte-4] Paul T. Nyffeler, Sergio Gonzalez Durón, Michael D. Burkart, Stéphane P. Vincent, Chi-Huey Wong: Selectfluor: Mechanisms and Applications . In: Angewandte Chemie . tape 117 , no. 2 , January 2005, p. 196-217 , doi : 10.1002 / anie.200400648 .

[banks-5] R. Eric Banks, Suad N. Mohialdin-Khaffaf, G. Sankar Lal, Iqbal Sharif, Robert G. Syvret: 1-Alkyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octane salts: a novel family of electrophilic fluorinating agents . In: Journal of the Chemical Society, Chemical Communications . No. 8 , 1992, pp. 595 , doi : 10.1039 / C39920000595 .

[synlett-6] Laxmi Manral: Selectfluor (F-TEDA-BF ₄ ) C ₇ H ₁₄ B ₂ ClF ₉ N ₂ . In: Synlett . No. 5 , 2006, p. 0807-0808 , doi : 10.1055 / s-2006-933124 .