(1H-1,2,3-benzotriazol-1-yloxy)bis(piperidin-1-yl)methylium; hexafluoro-λ5-phosphanuide

• ChemBase ID: 150079
• Molecular Formular: C17H24F6N5OP
• Molecular Mass: 459.3695402
• Monoisotopic Mass: 459.16226636
• SMILES: c1ccc2c(c1)nnn2OC(=[N+]1CCCCC1)N1CCCCC1.F[P-](F)(F)(F)(F)F
• Canonical SMILES: C1CCN(CC1)C(=[N+]1CCCCC1)On1nnc2c1cccc2.F[P-](F)(F)(F)(F)F
• InChI: InChI=1S/C17H24N5O.F6P/c1-5-11-20(12-6-1)17(21-13-7-2-8-14-21)23-22-16-10-4-3-9-15(16)18-19-22;1-7(2,3,4,5)6/h3-4,9-10H,1-2,5-8,11-14H2;/q+1;-1
• InChIKey: YNOBMGHLCWIWCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1H-1,2,3-benzotriazol-1-yloxy)bis(piperidin-1-yl)methylium; hexafluoro-λ^5-phosphanuide; 1-[(1H-1,2,3-benzotriazol-1-yloxy)(piperidin-1-yl)methylidene]-1λ^5-piperidin-1-ylium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: (1,2,3-benzotriazol-1-yloxy)bis(piperidin-1-yl)methylium hexafluorophosphate; 1-[(1,2,3-benzotriazol-1-yloxy)(piperidin-1-yl)methylidene]-1λ^5-piperidin-1-ylium hexafluorophosphate
• Synonyms: HBPipU; O-(Benzotriazol-1-yl)-N,N,N′,N′-bis(pentamethylene)uronium hexafluorophosphate; (Benzotriazol-1-yloxy)dipiperidinocarbenium hexafluorophosphate; O-Benzotriazol-1-yl-N,N,N′,N′-bis(pentamethylene)uronium hexafluorophosphate; O-苯并三唑-1-基-N,N,N',N'-二(五亚甲基)六氟磷酸脲; (苯并三氮唑-1-基氧基)二哌啶碳鎓六氟磷酸盐; (苯并三氮唑-1-基氧基)二哌啶碳六氟磷酸盐

Database IDs

• CAS Number: 190849-64-0; 206752-41-2
• MDL Number: MFCD01882881; MFCD00191769
• PubChem SID: 24847806; 162244241; 24866324
• PubChem CID: 10863473

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.32176
• LogD (pH = 7.4): -0.3217607
• Log P: -0.3217607
• Molar Refractivity: 101.2941 cm^3
• Polarizability: 35.377674 Å^3
• Polar Surface Area: 46.42 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble0.1 g/mL, clear
• Melting Point: 206 °C (dec.); 206 °C (dec.)(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC); 98%
• Empirical Formula (Hill Notation): C17H24F6N5OP

DETAILS

Sigma Aldrich - 420271

Packaging
1 g in glass bottle

Sigma Aldrich - 12792

Other Notes
Recent studies show that crystal and solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound3; Non-hygroscopic, extremely reactive reagent for peptide coupling. It is an analogue of the bis(tetramethylene) derivative described recently4
Packaging
5 g in glass bottle
Application
Reactant used for: comparison of racemization during peptide coupling1 esterification of nucleosides to solid phase supports for oligonucleotide synthesis2