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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-Nummer
4071-88-9
Synonyme
ETSA
(Trimethylsilyl)acetic acid ethyl ester

Größe Preis ($) Menge Verfügbarkeit
10g 53,25
50g 208,06
250g 678,40
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Ethyl (trimethylsilyl)acetate, 98+%

MDL
MFCD00009172
EINECS
223-783-2

Chemische Eigenschaften

Formel
(CH3)3SiCH2CO2CH2CH3
Molmasse
160.29
Siedepunkt
156-158°
Flammpunkt
35°(95°F)
Dichte
0.876
Brechungsindex
1.4150
Sensitivität
Moisture Sensitive
Löslichkeit
Decomposes in water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H226

Flammable liquid and vapour.

Sicherheitshinweise: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
1755902
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2931.90
TSCA
No

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