(1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE
Synonym(s):Cyclopropanone ethyl trimethylsilyl acetal
- CAS NO.:27374-25-0
- Empirical Formula: C8H18O2Si
- Molecular Weight: 174.31
- MDL number: MFCD00074986
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-04-23 13:52:06
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.
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 | n |
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) |
Flame Flammables GHS02 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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