1-[fluoro(pyrrolidin-1-yl)methylidene]-1λ5-pyrrolidin-1-ylium; hexafluoro-λ5-phosphanuide

• ChemBase ID: 152382
• Molecular Formular: C9H16F7N2P
• Molecular Mass: 316.1993234
• Monoisotopic Mass: 316.09393269
• SMILES: C1CCN(C1)C(=[N+]1CCCC1)F.F[P-](F)(F)(F)(F)F
• Canonical SMILES: F[P-](F)(F)(F)(F)F.FC(=[N+]1CCCC1)N1CCCC1
• InChI: InChI=1S/C9H16FN2.F6P/c10-9(11-5-1-2-6-11)12-7-3-4-8-12;1-7(2,3,4,5)6/h1-8H2;/q+1;-1
• InChIKey: MNJUGQKOHJQOCK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[fluoro(pyrrolidin-1-yl)methylidene]-1λ^5-pyrrolidin-1-ylium; hexafluoro-λ^5-phosphanuide; (1E)-1-[fluoro(pyrrolidin-1-yl)methylidene]-1λ^5-pyrrolidin-1-ylium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: 1-[fluoro(pyrrolidin-1-yl)methylidene]-1λ^5-pyrrolidin-1-ylium hexafluorophosphate; (1E)-1-[fluoro(pyrrolidin-1-yl)methylidene]-1λ^5-pyrrolidin-1-ylium hexafluorophosphate
• Synonyms: BTFFH; Fluoro-dipyrrolidinocarbenium hexafluorophosphate; Fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate; Fluorobis(tetramethylene)formamidinium hexafluorophosphate; Bis(tetramethylene)fluoroformamidinium hexafluorophosphate; 氟代二吡咯烷碳鎓六氟磷酸盐; 双(四亚甲基)氟代甲酰胺六氟磷酸; 双(四亚甲基)氟代甲酰胺 六氟磷酸

Database IDs

• CAS Number: 164298-25-3
• MDL Number: MFCD02683430
• PubChem SID: 24850472; 162246527
• PubChem CID: 10935980

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -2.1829324
• LogD (pH = 7.4): -2.1829324
• Log P: -2.1829324
• Molar Refractivity: 58.8827 cm^3
• Polarizability: 17.722263 Å^3
• Polar Surface Area: 6.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 154-160 °C; ca 155°C

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN1759
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (T)
• Empirical Formula (Hill Notation): C9H16F7N2P

DETAILS

Sigma Aldrich - 17380

Other Notes
Convenient peptide coupling reagent2,3
Packaging
5, 25 g in poly bottle
Application
Reagent for synthesis of immonium-type coupling reagents1

REFERENCES

• Reagent for peptide coupling via the acyl fluoride, which may be generated in situ without separate isolation, and has been found advantageous for solid-phase synthesis of peptides incorporating sensitive amino acids for which the acid fluoride is of limited stability: Chem. Lett., 671 (1998). For peptide reagents, see Appendix 6.