Ethyl (trimethylsilyl)acetate

• Catalog No.: A17707
• CAS Number: 4071-88-9
• M. F.: C7H16O2Si
• M. W.: 160.28624
• Purity: 98+%

SYNONYMS

• Title: (三甲基硅基)醋酸乙酯
• IUPAC name: ethyl 2-(trimethylsilyl)acetate
• IUPAC Traditional name: ethyl 2-(trimethylsilyl)acetate
• Synonyms: (Trimethylsilyl)acetic acid ethyl ester; ETSA

DATABASE IDS

• MDL Number: MFCD00009172
• EC Number: 223-783-2
• Beilstein Number: 1755902
• CAS Number: 4071-88-9

PROPERTIES

• Purity: 98+%
• Boiling Point: 156-158°C
• Density: 0.876
• Flash Point: 35°C(95°F)
• Refractive Index: 1.4150
• GHS Hazard statements: H226
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Risk Statements: 10
• Safety Statements: 7-33-43-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 3
• UN Number: UN3272
• Packing Group: III

REFERENCES

• Reagent for silylation, under nucleophilic catalysis by TBAF, particularly of sensitive substrates, since the by-product (ethyl acetate) is neutral and filtration is avoided: J. Am. Chem. Soc., 98, 2346 (1976).Alcohols, phenols, ketones, thiols, carboxylic acids and terminal alkynes can be silylated: Bull. Chem. Soc. Jpn., 54, 805 (1981). For conversion of ketones to silyl enol ethers, see: Org. Synth. Coll., 7, 512 (1990).
• Aromatic aldehydes undergo F^- promoted Reformatsky-like addition: Tetrahedron Lett., 1699 (1976). Further heating results in Peterson-type elimination to give the ɑ?-unsaturated ester: J. Org. Chem., 60, 6582 (1995):
  
• Grignard reagents give tertiary carbinols which give 1,1-disubstituted ethylenes by Peterson elimination: Tetrahedron Lett., 23, 1035 (1982). See Appendix 4.