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Ethyl (trimethylsilyl)acetate

Product Name
Ethyl (trimethylsilyl)acetate
CAS No.
4071-88-9
Chemical Name
Ethyl (trimethylsilyl)acetate
Synonyms
ETSA;2-trimethylsilylbutanoate;Ethyl(Trimethylsily)Acetate;ETHYL (TRIMETHYLSILYL)ACETATE;ETHYL(2-TRIMETHYLSILYL)ACETATE;ETHYL TRI METHYLSILYLACETATE 99%;Ethyl (trimethylsilyl)acetate,97%;Ethyl acetatethree Methylsilicone;Ethyl (trimethylsilyl)acetate, 98+%;(TRIMETHYLSILYL)ACETIC ACID ETHYL ESTER
CBNumber
CB7271085
Molecular Formula
C7H16O2Si
Formula Weight
160.29
MOL File
4071-88-9.mol
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Ethyl (trimethylsilyl)acetate Property

Boiling point:
156-159 °C (lit.)
Density 
0.876 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.415(lit.)
Flash point:
95 °F
storage temp. 
Inert atmosphere,Room Temperature
solubility 
sol ethereal and chlorinated solvents; reacts with protic solvents.
form 
clear liquid
color 
Colorless to Almost colorless
Specific Gravity
0.876
Water Solubility 
Decomposition
Hydrolytic Sensitivity
2: reacts with aqueous acid
Sensitive 
Moisture Sensitive
BRN 
1755902
CAS DataBase Reference
4071-88-9(CAS DataBase Reference)
NIST Chemistry Reference
Ethyl (trimethylsilyl)acetate(4071-88-9)
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Safety

Risk Statements 
10
Safety Statements 
16-24/25
RIDADR 
UN 3272 3/PG 3
WGK Germany 
3
10-21
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H226Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
209120
Product name
Ethyl trimethylsilylacetate
Purity
≥98%
Packaging
25g
Price
$244
Updated
2022/05/15
TCI Chemical
Product number
T1584
Product name
Ethyl (Trimethylsilyl)acetate
Purity
>93.0%(GC)
Packaging
5g
Price
$54
Updated
2024/03/01
TCI Chemical
Product number
T1584
Product name
Ethyl (Trimethylsilyl)acetate
Purity
>93.0%(GC)
Packaging
25g
Price
$162
Updated
2024/03/01
Alfa Aesar
Product number
A17707
Product name
Ethyl (trimethylsilyl)acetate, 98+%
Packaging
10g
Price
$59.65
Updated
2024/03/01
Alfa Aesar
Product number
A17707
Product name
Ethyl (trimethylsilyl)acetate, 98+%
Packaging
50g
Price
$257
Updated
2024/03/01
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Ethyl (trimethylsilyl)acetate Chemical Properties,Usage,Production

Chemical Properties

Ethyl trimethylsilylacetate is a clear colorless liquid. It is stable to the usual manipulations, and can be stored in glass containers for years without change of physical and spectral properties.

Uses

(silylating agent; source of an ethyl acetate anion equivalent.Ethyl trimethylsilylacetate is reactive to nucleophiles and readily undergoes desilylation reactions with acid or alkali,ethanol, and bromine.

Uses

Ethyl trimethylsilylacetate is used in the synthesis of ethyl-2,2-dibromo-2-(trimethylsilyl)acetate and α,β-unsaturated esters. It was also used to silylate the enolizable aldehydes and ketones.

Preparation

ethyl trimethylsilylacetate synthesis: Available by a Reformatsky reaction from ethyl bromoacetate, and by reaction of trimethylsilylmethylmagnesium chloride with ethyl chloroformate. An alternative approach requires the treatment of ethyl acetate with triphenylmethylsodium followed by chlorotrimethylsilane The use of a nitrogen base with ethyl acetate in THF followed by reaction with chlorotrimethylsilane results in a mixture of C- and O-silylation. The use of HMPA as additive in the reaction medium increases the amount of O-silylation to 90%. Similar methods can be used to prepare analogs.

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.

Purification Methods

Purify it by distilling ca 10g of reagent through a 15cm, Vigreux column (p 11) and then redistilling it through a 21cm glass helices-packed column [Hauze & Hauser J Am Chem Soc 75 994 1953]. Alternatively, dissolve it in Et2O, wash with H2O, dilute Na2CO3, dry over Na2CO3, evaporate Et2O, and distil it through a column of 15 theoretical plates. [Gold et al. J Am Chem Soc 70 2874 1948, Beilstein 4 IV 3974.]

Ethyl (trimethylsilyl)acetate Preparation Products And Raw materials

Raw materials

Preparation Products

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Ethyl (trimethylsilyl)acetate Suppliers

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View Lastest Price from Ethyl (trimethylsilyl)acetate manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Ethyl (trimethylsilyl)acetate 4071-88-9
Price
US $30.00-20.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200000KG
Release date
2024-07-30
Career Henan Chemical Co
Product
Ethyl (trimethylsilyl)acetate 4071-88-9
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1000KGS
Release date
2019-12-20

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