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

• ChemBase ID: 99116
• Molecular Formular: C11H16F6N5OP
• Molecular Mass: 379.2418202
• Monoisotopic Mass: 379.09966611
• SMILES: [P-](F)(F)(F)(F)(F)F.n1(c2ccccc2nn1)OC(=[N+](C)C)N(C)C
• Canonical SMILES: F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)On1nnc2c1cccc2)C
• InChI: InChI=1S/C11H16N5O.F6P/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1
• InChIKey: UQYZFNUUOSSNKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide; [(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: [(1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium; hexafluoro-$l^{5}-phosphanuide; [(1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylidene]dimethylazanium hexafluorophosphate
• Synonyms: HBTU; O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate; o-Benzotriazole-N,N,N’,N’-tetramethyl-uronium-hexafluoro-phosphate); O-(1H-Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; O-Benzotriazol-1-yl-N,N,N',N'-tetraMethyluroniuM hexafluorophosphate; O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate; O-(1H-苯并三唑-1-基)-N,N,N',N'-四甲基硫尿六氟磷酸盐; N,N,N′,N′-四甲基-O-(1H-苯并三氮唑)六氟磷酸脲; 苯并三氮唑-N,N,N′,N′-四甲基脲六氟磷酸酯

Database IDs

• CAS Number: 94790-37-1
• EC Number: 423-020-5
• MDL Number: MFCD00075445
• Beilstein Number: 7328329
• PubChem SID: 24847817; 162085413
• PubChem CID: 2733084

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

• Solubility: acetonitrile: soluble0.1 g/mL, clear
• Melting Point: 200 °C (dec.)(lit.); 200(dec.)°C; ca 200°C dec.

Safety Information

• Storage Warning: Irritant/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: 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: ≥98.0% (T); 97%; 98%
• Empirical Formula (Hill Notation): C11H16F6N5OP

DETAILS

Apollo Scientific Ltd - PC6587

Peptide coupling reagent.

Sigma Aldrich - B2778

Application
最近研究显示这种偶联试剂的晶体和溶液结构是胍的 N-氧化物形式，而不是一种脲化合物；1 用于肽合成的偶联剂；其优点在于：外消旋作用极低、反应条件简单、反应时间极短，以及极高的产率。2,3

Sigma Aldrich - 12804

Application
Recent studies show that crystal as well as solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound;1 Coupling reagent for peptide synthesis; advantages are: very low racemization, simple reaction conditions, very short reaction time, and high yields.2,3
Packaging
1, 5, 25 g in glass bottle

REFERENCES

• Peptide coupling reagent giving high yields with minimal racemization: Synthesis, 572(1984). See Appendix 6.