27374-25-0

Basic information

• Product Name: (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE
• Synonyms: (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE;[(1-ETHOXYCYCLOPROPYL)OXY]TRIMETHYLSILANE;1-ETHOXY-1-TRIMETHYLSILOXYL CYCLOPROPANE;CYCLOPROPANONE ETHYL TRIMETHYLSILYL ACETAL;SILANE, [(1-ETHOXYCYCLOPROPYL)OXY]TRIMETHYL-;1-Ethoxy-1-(trimethylsiloxy)cyclopropane;1-Ethoxy-1-(trimethylsilyloxy)cyclopropane;2- 1-Ethoxy-1-trimethylsiloxylcyclopropane
• CAS NO: 27374-25-0
• Molecular Formula: C₈H₁₈O₂Si
• Molecular Weight: 174.31
• Mol File: 27374-25-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 50-53 °C22 mm Hg(lit.)
• Flash Point: 79 °F
• Appearance: Clear colorless/Liquid
• Density: 0.867 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.25mmHg at 25°C
• Refractive Index: n20/D 1.407(lit.)
• Storage Temp.: Flammables area
• Solubility: insol H2O.
• BRN: 1924720
• CAS DataBase Reference: (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE(27374-25-0)
• EPA Substance Registry System: (1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE(27374-25-0)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 27374-25-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Physical properties

bp 50–53 °C/22 mmHg.

Uses

Different sources of media describe the Uses of 27374-25-0 differently. You can refer to the following data:
1. 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.
2. (1-Ethoxycyclopropoxy)trimethylsilane was used in the preparation of N-(1′-alkoxy)cyclopropyl-2-haloanilines.

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).

InChI:InChI=1/C8H18O2Si/c1-5-9-8(6-7-8)10-11(2,3)4/h5-7H2,1-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 623-71-2 ethyl 3-chloropropanoate 
• 7677-24-9 trimethylsilyl cyanide 
• 74592-24-8 Cyclopropanone Ethyl Hemiketal Magnesium Iodide 
• 13837-45-1 1-ethoxy-1-cyclopropanol 

Downstream Products

• 84098-47-5 4-Hydroxy-4-(4-nitro-phenyl)-butyric acid ethyl ester 
• 10264-12-7 N-benzylpropanamide 
• 137360-53-3 1-(benzylamino)-1-methoxycyclopropane 
• 137360-52-2 1-(benzylamino)cyclopropanecarbonitrile 
• 13837-45-1 1-ethoxy-1-cyclopropanol 
• 70623-01-7 N-[cyclopropyl(phenyl)methyl]propionamide 
• 137360-50-0 1-methoxy-1-<(methylbenzyl)amino>cyclopropane 
• 137360-49-7 (+/-)-1-<(methylbenzyl)amino>cyclopropanecarbonitrile 
• 96790-96-4 (E)-6-Phenyl-4-trimethylsilanyloxy-hex-5-enoic acid ethyl ester 
• 6270-17-3 ethyl 3-benzoylpropanoate 
• 2021-28-5 ethyl dihydrocinnamate 
• 4192-77-2 ethyl cinnamate 
• 121748-58-1 ethyl (trans)-6-phenyl-4-oxo-5-hexenoate 
• 22768-07-6 (E)-ethyl 5-phenylpent-4-enoate 

Relevant articles and documents

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Enantioselective organocatalytic iodination-initiated Wagner-Meerwein rearrangement

The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent S9 and the lipophilic phosphoric acid L9 act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcohols A x to β-iodo spiroketones Bx in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement.

Process for production of 1-alkoxy-1-trimethylsilyloxy cyclopropanes

The present invention provides a process for producing 1-alkoxy-1-trimethylsilyloxycyclopropane represented by the following general formula: STR1 by reacting microgranular metallic sodium dispersed in a hydrocarbon solvent, β-halogenocarboxylic acid ester represented by the following general formula: STR2 and chlorotrimethylsilane. According to the present invention, by using no ether compound solvent (the ether compound solvent has various problems in safety) and using microgranular metallic sodium dispersed in a hydrocarbon solvent, 1-alkoxy-1-trimethylsilyloxycyclopropane can be industrially produced simply (no special apparatus is required) at an advantageous cost at a yield at least equal to that obtained when an ether is used as solvent.