209120
Ethyl trimethylsilylacetate
≥98%
Synonym(s):
ETSA
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About This Item
Linear Formula:
(CH3)3SiCH2CO2C2H5
CAS Number:
Molecular Weight:
160.29
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-783-2
Beilstein/REAXYS Number:
1755902
MDL number:
Product Name
Ethyl trimethylsilylacetate, ≥98%
InChI key
QQFBQBDINHJDMN-UHFFFAOYSA-N
InChI
1S/C7H16O2Si/c1-5-9-7(8)6-10(2,3)4/h5-6H2,1-4H3
SMILES string
CCOC(=O)C[Si](C)(C)C
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.)
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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
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.
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
<73.4 °F - closed cup
flash_point_c
< 23 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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New synthesis of. alpha.,. beta.-unsaturated carboxylic esters.
Shimoji K, et al.
Journal of the American Chemical Society, 96(5), 1620-1621 (1974)
Synthetic Communications, 19, 2441-2441 (1989)
Synthesis and Cleavage of Ethyl Trimethylsilylacetate1, 2.
Gold JR, et al.
Journal of the American Chemical Society, 70(9), 2874-2876 (1948)
Journal of the Chemical Society. Perkin Transactions 1, 3217-3217 (1988)
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.
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