Ethyl N-cyanoethanimideate Chemical Properties

Melting point:

78-81 °C(Solv: ethyl ether (60-29-7))

Boiling point:

133.2±23.0 °C(Predicted)

Density 

0.94

refractive index 

1.45

Flash point:

34°

storage temp. 

2-8°C

pka

-2.94±0.50(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C5H8N2O/c1-3-8-5(2)7-4-6/h3H2,1-2H3

InChIKey

PLVWUINOWYHRAA-UHFFFAOYSA-N

SMILES

C(=NC#N)(OCC)C

CAS DataBase Reference

1558-82-3(CAS DataBase Reference)

Safety Information

RIDADR 

UN3273

HS Code 

2926.90.5050

HazardClass 

3, 6.1

Ethyl N-cyanoethanimideate Usage And Synthesis

Preparation

To a flask equipped as in Preparation 2-6 is added 162.0 gm (1.0 mole) of ethyl orthoacetate, 42.0 gm (1.0 mole) of cyanamide, and 134.0 gm (2.0 moles) of acetic anhydride. The reaction mixture is heated to 130-140°C and the ethyl acetate and acetic acid are distilled over. The heat is removed until the initial vigorous reaction subsides and then the heat­ing is continued at 135-140°C until most of the remaining ethyl acetate and acetid acid have distilled over (approx. 1 hr). The residue is then distilled under reduced pressure to afford 100.8 gm (90%), b.p. 90-95°C (20 mm Hg).

Synthesis

General methodology: The compound was synthesized with reference to literature methods. The standard procedure we used is detailed below: the mixed system of the original triethyl acetate (0.12 mol), cyanamide (0.1 mol) and a small amount of acetic acid (a few drops) was refluxed for 6 hours, followed by distillation and purification under reduced pressure (14 mmHg).

References

[1] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 5, p. 759 - 764
[2] Patent: US5750545, 1998, A
[3] Patent: WO2008/42928, 2008, A2. Location in patent: Page/Page column 33
[4] Patent: WO2008/42928, 2008, A2. Location in patent: Page/Page column 33
[5] Journal of Organic Chemistry, 1963, vol. 28, p. 1816 - 1821

Ethyl N-cyanoethanimideate(1558-82-3)Related Product Information

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