ChemicalBook CAS DataBase List ETHYL 2-CYANOACRYLATE

ETHYL 2-CYANOACRYLATE synthesis

5synthesis methods

Product Name:ETHYL 2-CYANOACRYLATE
CAS Number:7085-85-0
Molecular formula:C6H7NO2
Molecular Weight:125.13

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.

50-00-0 Synthesis

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7085-85-0
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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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