[(dimethylamino)({3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy})methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide

• ChemBase ID: 100325
• Molecular Formular: C10H15F6N6OP
• Molecular Mass: 380.2298802
• Monoisotopic Mass: 380.09491508
• SMILES: n1(c2c(cccn2)nn1)OC(=[N+](C)C)N(C)C.[P-](F)(F)(F)(F)(F)F
• Canonical SMILES: F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)On1nnc2c1nccc2)C
• InChI: InChI=1S/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
• InChIKey: JNWBBCNCSMBKNE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(dimethylamino)({3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy})methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide; [(dimethylamino)({3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy})methylidene]dimethylazanium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: [(dimethylamino)({[1,2,3]triazolo[4,5-b]pyridin-3-yloxy})methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide; [(dimethylamino)({[1,2,3]triazolo[4,5-b]pyridin-3-yloxy})methylidene]dimethylazanium; hexafluoro-λ^5-phosphanuide; [(dimethylamino)({[1,2,3]triazolo[4,5-b]pyridin-3-yloxy})methylidene]dimethylazanium hexafluorophosphate
• Synonyms: O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; HATU; N-[(Dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethylaminium hexafluorophosphate; N-[(Dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate; HATU; 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, ChemDose™ tablets; 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate impregnated tablets; N-[(Dimethylamino)-1H-1,2,3-triazolo-[4,5,b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide impregnated tablets; ChemDose™ 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate tablets; HATU impregnated tablets; N,N,N′,N′-四甲基-O-(7-氮杂苯并三唑-1-基)六氟磷酸脲; ChemDose™ O-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基脲六氟磷酸酯片剂; HATU 浸渍片剂; O-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基脲六氟磷酸酯，ChemDose™ 片剂; N,N,N′,N′-四甲基-O-(7-氮杂苯并三唑-1-基)六氟磷酸脲浸渍片剂; O-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基脲六氟磷酸酯浸渍片剂

Database IDs

• CAS Number: 148893-10-1
• MDL Number: MFCD00274639
• PubChem SID: 162086526; 24847146; 24868183
• PubChem CID: 9886157
• Chemspider ID: 8061830
• Wikipedia Title: HATU

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -3.0952623
• LogD (pH = 7.4): -3.0952623
• Log P: -3.0952623
• Molar Refractivity: 85.0227 cm^3
• Polarizability: 24.284819 Å^3
• Polar Surface Area: 59.08 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 183-185 °C(lit.); 183-188 °C (dec.); 186(dec.)°C

Safety Information

• Storage Warning: Irritant/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Explosive (E); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 2-36/37/38; 36/37/38
• Safety Statements: 26; 26-35
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H228-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P210-P261-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% (CHN); 97%
• Matrix: magnesium aluminometasilicate base material
• Empirical Formula (Hill Notation): C10H15F6N6OP

DETAILS

Sigma Aldrich - 685739

Frequently Asked Questions
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Legal Information
ChemDose is a trademark of Reaxa Ltd.

Sigma Aldrich - 445460

Application
Peptide coupling reagent.
Preparation of N-arylsulfonamide-linked peptides by solid-phase synthesis.1
Reagent for: Synthesis of Aurora A kinase inhibitors1 HPLC assay to determine D- and L- acid enantiomers in human plasma2 Amide bond formation reactions3Catalyst for: Selective acylation4 Selecocyclization-oxidation deselenation sequence5
Packaging
1, 5 g in glass bottle
25 g in poly bottle

Sigma Aldrich - 11373

Other Notes
Recent studies show that crystal as well as solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound;6 Advantageous coupling reagent for solid-phase peptide synthesis7.
Packaging
1, 5, 25 g in poly bottle
Application
Reagent for: Synthesis of Aurora A kinase inhibitors1 HPLC assay to determine D- and L- acid enantiomers in human plasma2 Amide bond formation reactions3Catalyst for: Selective acylation4 Selecocyclization-oxidation deselenation sequence5