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ChemicalBook CAS DataBase List ETHYL 2-CYANOACRYLATE
7085-85-0

ETHYL 2-CYANOACRYLATE synthesis

5synthesis methods
Ethyl cyanoacrylate is an acrylate compound used in instant glues to mend broken nails and to adhere glue-impregnated silk or linen to the nail plate. It was prepared from paraformaldehyde and ethylcyanoacetate  by stirring in acetonitrile with ytterbium triflate for 23h at room temperature.
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Yield:7085-85-0 70.67%

Reaction Conditions:

Stage #1:formaldehyd;ethyl 2-cyanoacetate in acetonitrile at 90; for 0.5 h;
Stage #2: with ytterbium(III) triflate in acetonitrileTemperature;Solvent;

Steps:

1 Example 1 :
To a 25ml round bottomed flask was added 1.80g (0096) (60mmol) of paraformaldehyde, 3.39g (30mmol) of ethyl (0097) cyanoacetate and lOmL of acetonitrile . The flask was fitted with a reflux condenser and magnetic stirrer before being immersed in an oil bath at a temperature of 90°C. The mixture was stirred at this temperature for a period of time of 30 minutes before a solution of 1.86g (3mmol, 10mol%) ytterbium triflate in 5mL of acetonitrile was added. The reaction was stopped at 23 hours. The relative conversion of cyanoacetate to cyanoacrylate was monitored by 500MHz 1E NMR. (0098) Relative Conversion by NMR: 17hr 55 59 (0099) 19hr 60 98 (0100) 21hr 66 58 (0101) 23hr 70 67

References:

HENKEL IP & HOLDING GMBH;DUFFY, Cormac;PHELAN, Marisa;BURNS, Barry WO2018/114458, 2018, A1 Location in patent:Paragraph 0049; 0050

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