ETHYL 2-(TRIMETHYLSILYLMETHYL)ACRYLATE

ETHYL 2-(TRIMETHYLSILYLMETHYL)ACRYLATE Property

Boiling point:

70-72 °C/10 mmHg (lit.)

Density 

0.897 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.438(lit.)

Flash point:

140 °F

storage temp. 

2-8°C

form 

liquid

BRN 

4658894

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

1993

WGK Germany 

3

F 

10-21

HazardClass 

3.2

PackingGroup 

III

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ETHYL 2-(TRIMETHYLSILYLMETHYL)ACRYLATE Chemical Properties,Usage,Production

Uses

2-Ethoxycarbonylallyltrimethylsilane is used for 2-ethoxycarbonylallylation of aldehydes and acetals; the allylation products are useful precursors to α- methylene-γ-butyrolactones; precursor of allyl cation equivalents for [3 + 2] and [3 + 4] cycloadditions.

Preparation

Preparative Methods of 2-Ethoxycarbonylallyltrimethylsilane: a three-step synthesis from Diethyl Malonate has been reported. t-Butyl and trimethylsilyl esters are also prepared by this method. Syntheses from ethyl diethylphosphonoacetate and ethyl α-bromoacrylate also have been reported, but the simplest procedure involves the reaction of ethoxalyl chloride with two equivalents of Trimethylsilylmethylmagnesium Chloride followed by treatment with Thionyl Chloride (53% yield). The CeIII-mediated reaction of trimethylsilylmethylmagnesium chloride with Diethyl Oxalate is also reported to give 2- ethoxycarbonylallyltrimethylsilane in 45% yield.

storage

2-Ethoxycarbonylallyltrimethylsilane can be stored in a glass bottle.