(Z)-(trimethylsilyl N-(trimethylsilyl)ethenecarboximidate)

• ChemBase ID: 301840
• Molecular Formular: C8H21NOSi2
• Molecular Mass: 203.42944
• Monoisotopic Mass: 203.11616736
• SMILES: C/C(=N/[Si](C)(C)C)/O[Si](C)(C)C
• Canonical SMILES: C/C(=N/[Si](C)(C)C)/O[Si](C)(C)C
• InChI: InChI=1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8-
• InChIKey: SIOVKLKJSOKLIF-HJWRWDBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (Z)-(trimethylsilyl N-(trimethylsilyl)ethenecarboximidate)
• IUPAC Traditional name: (Z)-(trimethylsilyl N-(trimethylsilyl)ethenecarboximidate)
• Synonyms: BSA; N,O-Bis(trimethylsilyl)acetamide; N,O-双三甲硅基乙酰胺

Database IDs

• CAS Number: 10416-59-8
• EC Number: 233-892-7
• MDL Number: MFCD00008270
• Beilstein Number: 1306669

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7573494
• LogD (pH = 7.4): 3.0714154
• Log P: 3.1974
• Molar Refractivity: 47.6538 cm^3
• Polarizability: 22.749172 Å^3
• Polar Surface Area: 21.59 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -24°C
• Boiling Point: 71-73°C/35mm
• Flash Point: 42°C(107°F)
• Density: 0.829
• Refractive Index: 1.4170

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: AK3000000
• European Hazard Symbols: Corrosive (C); X
• UN Number: UN2920
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 10-14-22-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Hazard statements: H301-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A

Product Information

• Purity: 95%

REFERENCES

• O-Silylation in the presence of TBAF (0.02 equiv.) occurs under very mild conditions: Tetrahedron Lett., 35, 8409 (1994).
• Powerful silylation reagent for a wide range of functional groups under mild conditions. See Appendix 4. Reviews: J. Prakt. Chem./ Chem. Ztg., 337, 332 (1995); Synthesis, 357 (1998). Unlike halosilanes, silylated amides often need no added base catalysts. For an example of use without added solvent or catalyst for the silylation of a tertiary ɑ-hydroxy ketone, see: Org. Synth. Coll., 7, 381 (1990). Silylating power can be increased in polar solvents such as DMF or acetonitrile, or by addition of acidic catalysts, often TMS chloride, or an acid such as TFA or HCl.
• BSA catalyzes the acylation of acylphosphoranes with activated derivatives of carboxylic acids. Subsequent ozonolysis, or oxidation with singlet oxygen or dimethyldioxirane, provides a route to 1,2,3-triketones: J. Org. Chem., 54, 2785 (1989); 60, 8231 (1995):