[(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium; tetrafluoroboranuide

• ChemBase ID: 100171
• Molecular Formular: C9H16BF4N3O3
• Molecular Mass: 301.0462528
• Monoisotopic Mass: 301.12208467
• SMILES: N1(C(=O)CCC1=O)OC(=[N+](C)C)N(C)C.[B-](F)(F)(F)F
• Canonical SMILES: F[B-](F)(F)F.O=C1CCC(=O)N1OC(=[N+](C)C)N(C)C
• InChI: InChI=1S/C9H16N3O3.BF4/c1-10(2)9(11(3)4)15-12-7(13)5-6-8(12)14;2-1(3,4)5/h5-6H2,1-4H3;/q+1;-1
• InChIKey: YEBLHMRPZHNTEK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium; tetrafluoroboranuide
• IUPAC Traditional name: [(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene]dimethylazanium tetrafluoroborate
• Synonyms: O-(N-Succinimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate; N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate; TSTU; N-{(Dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene}-N-methylmethylaminium tetrafluoroborate; O-(N-Succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2-Succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate; O-(N-琥珀酰亚胺基)-N,N,N′,N′-四甲基四氟硼酸脲; N,N,N′,N′-四甲基-O-(N-琥珀酰亚胺)脲四氟硼酸盐; 2-琥珀酰亚胺基-1,1,3,3-四甲基脲鎓四氟硼酸酯

Database IDs

• CAS Number: 105832-38-0
• EC Number: 000-000-0
• MDL Number: MFCD00077875
• PubChem SID: 24888487; 162087384; 24864036
• PubChem CID: 9857522

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: soluble0.1 g/mL, clear
• Melting Point: 195-200 °C; 195-200°C; 198-201 °C(lit.); 198-201°C

Safety Information

• Storage Warning: Irritant/Light Sensitive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 97%; 98%
• Grade: purum
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C9H16BF4N3O3

DETAILS

Sigma Aldrich - 385530

Packaging
1, 5 g in glass bottle
Application
Reactant for: Linking sensor molecules with amino groups to amino functionalized AFM tips1 Reactant for synthesis of: A polymer supported oranotin reagent for prosthetic group labeling of biological macromolecules with radioiodine2 L-Rhamnose antigen3 Fluorinated rhodamines for optical microscopy and nanoscopy3 c(RGDyK) targeted SN38 prodrug4 Polyelectrolytes for thin film construction5

Sigma Aldrich - 85972

Other Notes
Reagent for the clean in-situ formation of N-succinimidyl active esters6; Coupling reagent for peptide synthesis7,8
Application
Reactant for: Linking sensor molecules with amino groups to amino functionalized AFM tips1 Reactant for synthesis of: A polymer supported oranotin reagent for prosthetic group labeling of biological macromolecules with radioiodine2 L-Rhamnose antigen3 Fluorinated rhodamines for optical microscopy and nanoscopy3 c(RGDyK) targeted SN38 prodrug4 Polyelectrolytes for thin film construction5

REFERENCES

• Reagent for the formation of succinimidyl active esters, used for attaching Ru complexes to 5'-amino modified oligonuleotides for use in time-resolved fluorescence techniques: Helv. Chim. Acta, 71, 2085 (1988). In situ formation of succinimidyl active esters can be used in peptide coupling in aqueous solutions: Tetrahedron Lett., 30, 1927 (1989). For peptide reagents, see Appendix 6.