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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+%

Numéro de CAS
4071-88-9
Synonymes
ETSA
(Trimethylsilyl)acetic acid ethyl ester

Conditionnement Prix ($) Quantité Disponibilité
10g 53,30
50g 206,00
250g 865,00
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Ethyl (trimethylsilyl)acetate, 98+%

MDL
MFCD00009172
EINECS
223-783-2

Propriétés chimiques

Formule
(CH3)3SiCH2CO2CH2CH3
Poids moleculaire
160.29
Point d'ébullition
156-158°
Point d'éclair
35°(95°F)
Densité
0.876
Indice de réfraction
1.4150
Sensibilité
Moisture Sensitive
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226

Flammable liquid and vapour.

Mentions de prudence: 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.

Autres références

Beilstein
1755902
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2931.90
TSCA
No

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Analytique et matériel de laboratoire