tetrafluoroboranuide ethyl cyano({[(dimethylamino)(dimethyliminiumyl)methoxy]imino})formate

• ChemBase ID: 151080
• Molecular Formular: C10H17BF4N4O3
• Molecular Mass: 328.0715928
• Monoisotopic Mass: 328.1329837
• SMILES: [B-](F)(F)(F)F.CCOC(=O)/C(=N/OC(=[N+](C)C)N(C)C)/C#N
• Canonical SMILES: F[B-](F)(F)F.CCOC(=O)/C(=N/OC(=[N+](C)C)N(C)C)/C#N
• InChI: InChI=1S/C10H17N4O3.BF4/c1-6-16-9(15)8(7-11)12-17-10(13(2)3)14(4)5;2-1(3,4)5/h6H2,1-5H3;/q+1;-1
• InChIKey: FPQVGDGSRVMNMR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrafluoroboranuide ethyl cyano({[(dimethylamino)(dimethyliminiumyl)methoxy]imino})formate; (E)-(ethyl cyano({[(dimethylamino)(dimethyliminiumyl)methoxy]imino})formate); tetrafluoroboranuide
• IUPAC Traditional name: ethyl cyano({[(dimethylamino)(dimethyliminio)methoxy]imino})formate tetrafluoroborate; (E)-(ethyl cyano({[(dimethylamino)(dimethyliminio)methoxy]imino})formate) tetrafluoroborate
• Synonyms: N-[[[(1-Cyano-2-ethoxy-2-oxoethylidene)amino]oxy](dimethylamino)methylene]-N-methyl-methanaminium tetrafluoroborate; TOTU; O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N′,N′-tetramethyluronium tetrafluoroborate; O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; O-[(乙氧羰基)氰基亚甲基氨基]-N,N,N′,N′-四甲基脲四氟硼酸酯; O-[(乙氧基羰基)氰基甲胺]-N,N,N',N'-四甲基硫尿四氟硼酸盐

Database IDs

• CAS Number: 136849-72-4
• MDL Number: MFCD00192127
• PubChem SID: 24863898; 162245238
• PubChem CID: 9601231

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.8784304
• LogD (pH = 7.4): -1.8784304
• Log P: -1.8784304
• Molar Refractivity: 73.1883 cm^3
• Polarizability: 23.429152 Å^3
• Polar Surface Area: 77.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 143-146°C dec.; 144-145 °C; 145 °C (dec.)(lit.)

Safety Information

• Storage Warning: 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: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; 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% (CHN); 97%; 98%
• Linear Formula: C2H5O2CC(CN)=NOC[N(CH3)2]=N(CH3)2BF4

DETAILS

Sigma Aldrich - 382469

Packaging
1 g in glass bottle
Application
Reactant for:Watson-Crick pairing of oligonucleotides1Esterification of nucleosides to solid phase supports2Reagent for:Synthesis of selective integrin avβ3 antagonists3Design and synthesis of double stranded DNA libraries4Preparation of conformationally contrained β-amino acid derivatives5Synthesis and application of methyleneoxy pseudopeptide building blocks6

Sigma Aldrich - 02580

Other Notes
New uronium-based coupling reagent for peptide synthesis suitable for critical cases7
Application
Reactant for:Watson-Crick pairing of oligonucleotides1Esterification of nucleosides to solid phase supports2Reagent for:Synthesis of selective integrin avβ3 antagonists3Design and synthesis of double stranded DNA libraries4Preparation of conformationally contrained β-amino acid derivatives5Synthesis and application of methyleneoxy pseudopeptide building blocks6

REFERENCES

• Low racemization peptide coupling agent: Proc. 21st Eur. Pept. Symp., 1990, E. Giralt, D. Andren Eds., ESCOM, Leiden (1991), p143; Tetrahedron Lett., 33, 6625 (1992). See Appendix 6.