1-[(1H-1,2,3-benzotriazol-1-yloxy)(pyrrolidin-1-yl)methylidene]-1λ5-pyrrolidin-1-ylium; hexafluoro-λ5-phosphanuide

• ChemBase ID: 138453
• Molecular Formular: C15H20F6N5OP
• Molecular Mass: 431.3163802
• Monoisotopic Mass: 431.13096624
• SMILES: c1ccc2c(c1)nnn2OC(=[N+]1CCCC1)N1CCCC1.F[P-](F)(F)(F)(F)F
• Canonical SMILES: C1CCN(C1)C(=[N+]1CCCC1)On1nnc2c1cccc2.F[P-](F)(F)(F)(F)F
• InChI: InChI=1S/C15H20N5O.F6P/c1-2-8-14-13(7-1)16-17-20(14)21-15(18-9-3-4-10-18)19-11-5-6-12-19;1-7(2,3,4,5)6/h1-2,7-8H,3-6,9-12H2;/q+1;-1
• InChIKey: XKTRAGMCMJYRRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1H-1,2,3-benzotriazol-1-yloxy)(pyrrolidin-1-yl)methylidene]-1λ^5-pyrrolidin-1-ylium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: 1-[(1,2,3-benzotriazol-1-yloxy)(pyrrolidin-1-yl)methylidene]-1λ^5-pyrrolidin-1-ylium hexafluorophosphate
• Synonyms: HBPyU; (Benzotriazol-1-yloxy)dipyrrolidinocarbenium hexafluorophosphate; O-(Benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate; (苯并三氮唑-1-基氧基)二吡咯烷碳六氟磷酸盐; O-(苯并三唑-1-基)-N,N,N′,N′-二(四亚甲基)六氟磷酸脲

Database IDs

• CAS Number: 105379-24-6
• MDL Number: MFCD00191770
• PubChem SID: 24847825; 162232709; 24866323
• PubChem CID: 13685355

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.4334575
• LogD (pH = 7.4): -1.433457
• Log P: -1.433457
• Molar Refractivity: 102.309 cm^3
• Polarizability: 31.723886 Å^3
• Polar Surface Area: 46.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 176 °C (dec.)(lit.)

Safety Information

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

Product Information

• Purity: ≥98.0%; 98%
• Empirical Formula (Hill Notation): C15H20F6N5OP

DETAILS

Sigma Aldrich - 420263

Packaging
1 g in glass bottle
Application
Catalyst for synthesis of dyes1Reagent for peptide coupling 2

Sigma Aldrich - 12809

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 giving low racemization. Reaction by-products are non-cytotoxic4
Packaging
5 g in glass bottle
Application
Catalyst for synthesis of dyes1Reagent for peptide coupling 2