1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium; bis(tetrafluoroboranuide)

• ChemBase ID: 7710
• Molecular Formular: C7H14B2ClF9N2
• Molecular Mass: 354.2600888
• Monoisotopic Mass: 354.08879092
• SMILES: [N+]12(CC[N+](CCl)(CC1)CC2)F.[B-](F)(F)(F)F.[B-](F)(F)(F)F
• Canonical SMILES: F[B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](CC1)(CC2)F
• InChI: InChI=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
• InChIKey: TXRPHPUGYLSHCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium; bis(tetrafluoroboranuide); 4-(chloromethyl)-1-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium; bis(tetrafluoroboranuide)
• IUPAC Traditional name: 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate; 4-(chloromethyl)-1-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate
• Synonyms: 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate); F-TEDA; 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate); N-Chloromethyl-N′-fluorotriethylenediammonium bis(tetrafluoroborate); Selectfluor® fluorinating reagent; N-Fluoro-N'-chloromethyltriethylenediamine bis(tetrafluoroborate); Selectfluor; 1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate); 1-(Chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate; F-TEDA-BF4; SELECTFLUOR Fluorinating Reagent; 1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷二(四氟硼酸)盐; 1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷二(四氟硼酸)盐; N-氯甲基-N′-氟三乙二铵双(四氟硼酸盐); Selectfluor® 氟化剂; 1-氯甲基-4-氟-1,4-重氮化二环2.2.2辛烷双(四氟硼酸盐)

Database IDs

• CAS Number: 140681-55-6
• EC Number: 414-380-4
• MDL Number: MFCD00142607
• Beilstein Number: 5368649
• PubChem SID: 160971017; 24867509
• PubChem CID: 2724933

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -4.414943
• LogD (pH = 7.4): -4.414943
• Log P: -4.414943
• Molar Refractivity: 56.7255 cm^3
• Polarizability: 16.74862 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 250°C dec; 260 °C(lit.); 260°C; ca 250°C dec.

Safety Information

• Storage Warning: IRRITANT, KEEP COLD, SELF-HEATING SOLID; Self-Heating/Harmful/Corrosive/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 3088; UN3088
• German water hazard class: 2
• Hazard Class: 4.2
• Packing Group: 2; II
• Risk Statements: 22-41-43-52/53
• Safety Statements: 21-26-36/37/39-61
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H252-H302-H317-H318-H412; H302-H317-H318-H412; H318-H302-H317-H313-H402-H412
• GHS Precautionary statements: P235 + P410-P273-P280-P305 + P351 + P338; P261-P280-P273-P270-P305+P351+P338; P273-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3088 4.2/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (NMR); 95+%; 98+%
• Concentration: >95% in F+ active
• Grade: purum
• Suitability: in accordance for 19F-, 1H-NMR
• Empirical Formula (Hill Notation): C7H14B2ClF9N2

DETAILS

Apollo Scientific Ltd - PC3728K

Electrophilic fluorinating agent. Ask for technical literature(SelectfluorR - Registered trademark of Air Products). Decomposes exothermally at >1000C

Sigma Aldrich - 439479

Application
A highly effective and versatile source of electrophilic fluorine.
Electrophilic fluorinating reagent used, e.g., in the preparation of fluorinated acylsilanes.
Fluorinating reagent that effects oxidative ring opening of 2,5-diarylfurans to cis-1,4-enediones.2 Also used for direct fluorination of silyl ketene acetals leading to α-fluoro-α-arylcarboxylic acids.3
Packaging
5, 25, 100 g in poly bottle
Citation
A review.1
Legal Information
Selectfluor is a registered trademark of Air Products & Chemicals, Inc.

Sigma Aldrich - 25140

Other Notes
Reagent for electrophilic fluorination 1,2,3; Selective oxidizing agent4

REFERENCES

• SELECTFLUOR is a registered trademark of Air Products & Chemicals Inc.
• Stabilized carbanions can be selectively mono- or difluorinated: J. Chem. Soc., Chem. Commun., 343 (1994); Tetrahedron, 51, 3587 (1995). Fluorinated steroids have been prepared from enol acetates or silyl enol ethers: J. Org. Chem., 58, 2791 (1993). 5-Fluoropyrimidine nucleosides can be obtained by treatment of protected nucleosides with the reagent in the presence of water or methanol, followed by elimination of the resulting fluorohydrin derivative: J. Org. Chem., 60, 7340 (1995).
• For application to N-fluorination of amines, see: Chem. Commun., 1196 (2001). Review of mechanistic insight and applications of the reagent: Angew. Chem. Int Ed., 44, 192 (2005).Brief feature on uses in synthesis: Synlett, 807 (2006). Review of electrophilic N-F fluorinating agents: Chem. Rev., 96, 1737 (1996).
• Water- and organic-soluble reagent developed by R. E. Banks and co-workers for electrophilic fluorination of a variety of substrates under mild conditions: USP 5,086,178 (1992 to Air Products & Chemicals, Inc.); review: J. Fluorine Chem., 87, 1 (1998). In acetonitrile, activated aromatics can be fluorinated in good yield: J. Chem. Soc., Perkin 1., 2069 (1996). Less active substrates can be fluorinated in the presence of triflic acid: Israel J. Chem., 39, 207 (1999). In acetonitrile, vinylsilanes undergo fluorodesilylation to give vinyl fluorides with retention of configuration: Chem. Commun., 233 (2001).
• For use in the synthesis of fluorinated carbohydrates by reaction with glycals, see: J. Am. Chem. Soc., 119, 11743 (1997); J. Org. Chem., 64, 5264 (1999).