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HomeProduct name list(1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

(1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

Synonym(s):Cyclopropanone ethyl trimethylsilyl acetal

(1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE Structural

What is (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE?

Chemical properties

clear colorless liquid

Physical properties

bp 50–53 °C/22 mmHg.

The Uses of (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

(1-Ethoxycyclopropoxy)trimethylsilane was used in the preparation of N-(1′-alkoxy)cyclopropyl-2-haloanilines.

The Uses of (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

The 1-Ethoxy-1-(trimethylsilyloxy)cyclopropane can be used as preparation of 3-metallopropionates; metal homoenolate precursor; γ-hydroxy esters; cyclopentenones; 3-aminopropionates; cyclopropylamine formation; 1-aminocyclopropanecarboxylic acids and 1-aminocyclopropanephosphonic acids; β- and γ-amino acids.
The 1-Ethoxy-1-(trimethylsilyloxy)cyclopropane is widely used in various reactions. Cyclization of optically pure β-halo esters gives cyclopropanone acetals enantiomerically pure at C-2 and a 1:1 diastereomeric mixture at C-1.
Use of Cyclopropanone Hemiacetals. Heating cyclopropanone hemiacetal at 100°Cin an aqueous buffer provides the cyclopropanone hydrate. It also serves as a source of homoenolate radical species with a catalytic amount of AgNO3.Use of Cyclopropanone Hemiacetals

Preparation

For the synthesis of the parent and the 2-monoalkyl-substituted compounds, reduction of ethyl 3- chloropropionate with sodium–potassium alloy in the presence of chlorotrimethylsilane in ether. A recent modification using ultrasound irradiation is much more convenient and more widely applicable. Other substituted derivatives are prepared by cyclopropanation of alkyl silyl ketene acetals with the Furukawa reagent (diiodomethane/diethylzinc).

Properties of (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

Boiling point: 50-53 °C/22 mmHg (lit.)
Density  0.867 g/mL at 25 °C (lit.)
refractive index  n20/D 1.407(lit.)
Flash point: 79 °F
storage temp.  Inert atmosphere,2-8°C
solubility  insol H2O.
form  Liquid
color  Clear colorless
Specific Gravity 0.867
Hydrolytic Sensitivity 7: reacts slowly with moisture/water
BRN  1924720
CAS DataBase Reference 27374-25-0

Safety information for (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

Signal word Warning
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H226:Flammable liquids
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

InChIKey BZMMRNKDONDVIB-UHFFFAOYSA-N

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