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Ethyl (trimethylsilyl)acetate, 98%, Thermo Scientific Chemicals
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Catalog number A17707.30
also known as A17707-30
Price (USD)/ Each
1,016.00
-
Quantity:
250 g
Price (USD)/ Each
1,016.00
Ethyl (trimethylsilyl)acetate, 98%, Thermo Scientific Chemicals
Catalog numberA17707.30
Price (USD)/ Each
1,016.00
-
Chemical Identifiers
CAS4071-88-9
IUPAC Nameethyl 2-(trimethylsilyl)acetate
Molecular FormulaC7H16O2Si
InChI KeyQQFBQBDINHJDMN-UHFFFAOYSA-N
SMILESCCOC(=O)C[Si](C)(C)C
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless
FormLiquid
Assay (GC)≥97.5%
Refractive Index1.4130-1.4170 @ 20°C
Ethyl trimethylsilylacetate is used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate. It was also used to silylate the enolizable aldehydes and ketones.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Ethyl trimethylsilylacetate is used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate. It was also used to silylate the enolizable aldehydes and ketones.
Solubility
Decomposes in water.
Notes
Moisture Sensitive. Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.
Ethyl trimethylsilylacetate is used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate. It was also used to silylate the enolizable aldehydes and ketones.
Solubility
Decomposes in water.
Notes
Moisture Sensitive. Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.
RUO – Research Use Only
General References:
- Thomas Poisson.; Vincent Gembus.; Sylvain Oudeyer.; Francis Marsais.; Vincent Levacher. Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination. J. Org. Chem. 2009, 74, (9), 3516-3519.
- O. W. Webster.; W. R. Hertler.; D. Y. Sogah.; W. B. Farnham.; T. V. RajanBabu. Group-transfer polymerization. 1. A new concept for addition polymerization with organosilicon initiators. J. Am. Chem. Soc. 1983, 105, (17), 5706-5708.
- 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 ɑß-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.