[(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide

• ChemBase ID: 100172
• Molecular Formular: C9H16F6N3O3P
• Molecular Mass: 359.2058202
• Monoisotopic Mass: 359.08334734
• SMILES: [P-](F)(F)(F)(F)(F)F.O(N1C(=O)CCC1=O)C(=[N+](C)C)N(C)C
• Canonical SMILES: F[P-](F)(F)(F)(F)F.O=C1CCC(=O)N1OC(=[N+](C)C)N(C)C
• InChI: InChI=1S/C9H16N3O3.F6P/c1-10(2)9(11(3)4)15-12-7(13)5-6-8(12)14;1-7(2,3,4,5)6/h5-6H2,1-4H3;/q+1;-1
• InChIKey: STWZCCVNXFLDDD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide; [(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: [(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide; [(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium hexafluorophosphate
• Synonyms: HSTU; O-(N-Succinimidyl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; O-(N-Succinimidyl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate; N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate; N,N,N′,N′-四甲基-O-(N-琥珀酸亚胺基)脲六氟磷酸盐; N,N,N′,N′-四甲基脲-O-(N-琥珀酸亚胺基)六氟磷酸盐

Database IDs

• CAS Number: 265651-18-1
• MDL Number: MFCD01863753
• PubChem SID: 162086270; 24846381
• PubChem CID: 16211151

CALCULATED PROPERTIES

• Acid pKa: 17.644016
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -3.8706825
• LogD (pH = 7.4): -3.8706825
• Log P: -3.8706825
• Molar Refractivity: 65.131 cm^3
• Polarizability: 20.799934 Å^3
• Polar Surface Area: 52.86 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble0.5 g/mL, slightly hazy, colorless
• Melting Point: 218-221 °C (dec.)

Safety Information

• Storage Warning: Irritant
• 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: -20°C

Product Information

• Purity: ≥99.0% (TLC/N)
• Empirical Formula (Hill Notation): C9H16F6N3O3P

DETAILS

Sigma Aldrich - 09668

Other Notes
Coupling reagent for peptide synthesis and the formation of other amides. Even in aqueous solution yields are excellent4,5
Application
Reactant for: Synthesis of liposomal contrast agents for magnetic resonance imaging1 Synthesis of thiol-reactive Cy5 derivatives2 Synthesis of protein labeling molecules3