N,O-Bis(trimethylsilyl)acetamide

• Catalog No.: L00183
• CAS Number: 10416-59-8
• M. F.: C8H21NOSi2
• M. W.: 203.42944
• Purity: 95%

SYNONYMS

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

DATABASE IDS

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

PROPERTIES

• Purity: 95%
• Boiling Point: 71-73°C/35mm
• Density: 0.829
• Flash Point: 42°C(107°F)
• Melting Point: -24°C
• Refractive Index: 1.4170
• GHS Hazard statements: H301-H314-H318-H226
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-14-22-34
• RTECS: AK3000000
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2920
• Packing Group: II

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):