209120
Ethyl trimethylsilylacetate
≥98%
Synonym(s):
ETSA
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About This Item
Linear Formula:
(CH3)3SiCH2CO2C2H5
CAS Number:
Molecular Weight:
160.29
Beilstein:
1755902
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
≥98%
form
liquid
refractive index
n20/D 1.415 (lit.)
bp
156-159 °C (lit.)
density
0.876 g/mL at 25 °C (lit.)
SMILES string
CCOC(=O)C[Si](C)(C)C
InChI
1S/C7H16O2Si/c1-5-9-7(8)6-10(2,3)4/h5-6H2,1-4H3
InChI key
QQFBQBDINHJDMN-UHFFFAOYSA-N
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General description
Reaction of ethyl trimethylsilylacetate (ETSA) with dilute hydrochloric acid, dilute alkali, anhydrous HCl, anhydrous bromine and absolute ethanol has been reported. ETSA undergoes condensation with aromatic aldehydes in the presence of base catalyst to yield β-trimethylsiloxycarboxylates. Lithium ETSA reacts with ketones to yield α,β-unsaturated esters.
Application
Ethyl trimethylsilylacetate (ETSA) was used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate. It was also used to silylate the enolizable aldehydes and ketones
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Flam. Liq. 2
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
<73.4 °F - closed cup
Flash Point(C)
< 23 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Synthesis and Cleavage of Ethyl Trimethylsilylacetate1, 2.
Gold JR, et al.
Journal of the American Chemical Society, 70(9), 2874-2876 (1948)
Synthetic Communications, 19, 2441-2441 (1989)
Mitsuru Shindo et al.
Chemical & pharmaceutical bulletin, 51(4), 477-478 (2003-04-04)
Aliphatic alpha,alpha-dibromo esters, precursors of ynolates, were synthesized via bromination of lithium alpha-bromo ester enolates with 1,2-dibromotetrafluoroethane in good yields. alpha-Trimethylsilyl-alpha,alpha-dibromo esters were synthesized via radical bromination.
Journal of the Chemical Society. Perkin Transactions 1, 3217-3217 (1988)
New synthesis of. alpha.,. beta.-unsaturated carboxylic esters.
Shimoji K, et al.
Journal of the American Chemical Society, 96(5), 1620-1621 (1974)
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