1-fluoropyridin-1-ium trifluoromethanesulfonate

• ChemBase ID: 9973
• Molecular Formular: C6H5F4NO3S
• Molecular Mass: 247.1674128
• Monoisotopic Mass: 246.99262691
• SMILES: F[n+]1ccccc1.FC(F)(F)S(=O)(=O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)C(F)(F)F.F[n+]1ccccc1
• InChI: InChI=1S/C5H5FN.CHF3O3S/c6-7-4-2-1-3-5-7;2-1(3,4)8(5,6)7/h1-5H;(H,5,6,7)/q+1;/p-1
• InChIKey: JFZMMCYRTJBQQI-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-fluoropyridin-1-ium trifluoromethanesulfonate
• IUPAC Traditional name: 1-fluoropyridin-1-ium triflate
• Synonyms: N-Fluoropyridinium trifluoromethanesulfonate; 1-Fluoropyridinium trifluoromethanesulfonate; 1-Fluoropyridinium triflate; N-Fluoropyridinium trifluoromethanesulphonate 99%; N-Fluoropyridinium triflate; N-Fluoropyridinium trifluoromethanesulfonate; 1-氟吡啶三氟甲磺酸盐; 三氟甲磺酸 N-吡啶鎓; N-氟吡啶鎓三氟甲磺酸盐

Database IDs

• CAS Number: 107263-95-6
• MDL Number: MFCD00013458
• Beilstein Number: 4222821
• PubChem SID: 160973280; 24859409
• PubChem CID: 2724576

CALCULATED PROPERTIES

• Acid pKa: -3.4301212
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.2283616
• LogD (pH = 7.4): -1.2283617
• Log P: 1.1480371
• Molar Refractivity: 15.8602 cm^3
• Polarizability: 7.460577 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 180-185°C; 185-186 °C(lit.); 185-187°C

Safety Information

• Storage Warning: Irritant; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 35
• Safety Statements: 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 95%; 98%; 99%
• Empirical Formula (Hill Notation): C6H5F4NO3S

DETAILS

Apollo Scientific Ltd - PC4202

Electrophilic fluorinating agent. Tet Lett., 27,3271,4465 (1986): alpha - fluoro ketones Chem Rev., 96, 1737 (1996): electrophilic fluorination.

Sigma Aldrich - 323659

Application
General purpose electrophilic fluorinating reagent.4
Reactant for:
• Pd-catalyzed arylation reactions1
• Preparation of small molecule botulinum neurotoxin A endopeptidase inhibitors2
• Fluorination agent3
Packaging
1, 5 g in glass bottle

REFERENCES

• Alkyl or silyl enol ethers give ɑ-fluoro ketones: Tetrahedron Lett., 27, 3271, 4465 (1986); Org. Synth. Coll., 8, 286 (1993). For regioselective mono-ɑ-fluorination of steroids bearing several silyl enol ether groups, see: J. Am. Chem. Soc., 112, 8563 (1990).
• Reagent for electrophilic fluorination:
• For a review of electrophilic N-F fluorinating agents, see: Chem. Rev., 96, 1737 (1996).