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4071-88-9 - Ethyl (trimethylsilyl)acetate, 98+% - ETSA - (Trimethylsilyl)acetic acid ethyl ester - A17707 - Alfa Aesar

A17707 Ethyl (trimethylsilyl)acetate, 98+%

CAS Number
4071-88-9
Synonyms
ETSA
(Trimethylsilyl)acetic acid ethyl ester

Size Price ($) Quantity Availability
10g 53.30
50g 206.00
250g 865.00
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Ethyl (trimethylsilyl)acetate, 98+%

MDL
MFCD00009172
EINECS
223-783-2

Chemical Properties

Formula
(CH3)3SiCH2CO2CH2CH3
Formula Weight
160.29
Boiling Point
156-158°
Flash Point
35°(95°F)
Density
0.876
Refractive Index
1.4150
Sensitivity
Moisture Sensitive
Solubility
Decomposes in water.

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.

Notes

Moisture Sensitive. Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.

Literature 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226

Flammable liquid and vapour.

Precautionary Statements: P210-P280a-P240-P241-P303+P361+P353-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1755902
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No

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