[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium; tetrafluoroboranuide

• ChemBase ID: 93510
• Molecular Formular: C11H16BF4N5O
• Molecular Mass: 321.0822528
• Monoisotopic Mass: 321.13840344
• SMILES: n1(c2ccccc2nn1)OC(=[N+](C)C)N(C)C.[B-](F)(F)(F)F
• Canonical SMILES: F[B-](F)(F)F.CN(C(=[N+](C)C)On1nnc2c1cccc2)C
• InChI: InChI=1S/C11H16N5O.BF4/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1
• InChIKey: JKEKMBGUVUKMQB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium; tetrafluoroboranuide
• IUPAC Traditional name: [(1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium tetrafluoroborate
• Synonyms: TBTU; O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate; O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate; [(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium; tetrafluoroboranuide; O-(1H-Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 2-(1h-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; 苯并三唑四甲基四氟硼酸; O-苯并三氮唑-N,N,N′,N′-四甲基脲四氟硼酸酯; O-(1H-苯并三唑-1-基)-N,N,N',N'-四甲基脲四氟磷酸盐

Database IDs

• CAS Number: 125700-67-6
• EC Number: 423-040-4
• MDL Number: MFCD00077413
• Beilstein Number: 7066325
• PubChem SID: 162080195; 24847819; 24864035
• PubChem CID: 2733207

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -2.2450523
• LogD (pH = 7.4): -2.2450519
• Log P: -2.2450519
• Molar Refractivity: 87.227 cm^3
• Polarizability: 25.814367 Å^3
• Polar Surface Area: 46.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 195-198°C dec.; 195-205(dec.)°C; 200 - 202°C; 205 °C (dec.)(lit.)
• Hydrophobicity(logP): 0.0

Safety Information

• Storage Warning: Flammable/Irritant/Light Sensitive/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: 26-35; 26-36; 26-37
• TSCA Listed: 否
• 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; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (N); 95%; 97%; 98%; 99%
• Linear Formula: C11H16N5O · BF4

DETAILS

Apollo Scientific Ltd - PC0921

Peptide coupling reagent.

Sigma Aldrich - B2903

Application
Coupling reagent which is ideally suited for solid-phase peptide synthesis.

Sigma Aldrich - 385522

Application
Coupling reagent which is ideally suited for solid-phase peptide synthesis.
Used in a study of ten different uronium and phosphonium salt-based coupling reagents in the synthesis of four model peptides. Also used as a coupling reagent in a multi-gram solid-phase synthesis of a tetrahydrocarbazole substituted dipeptide.

Sigma Aldrich - 12806

Application
Coupling reagent which is ideally suited for solid-phase peptide synthesis.
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 compound1; Coupling reagent which is ideally suited for solid-phase peptide synthesis.2
Packaging
1 kg in glass bottle
5, 25, 100, 250 g in glass bottle