Ethyl (ethoxymethylene)cyanoacetate Chemical Properties

Melting point:

49-51 °C(lit.)

Boiling point:

190-191 °C30 mm Hg(lit.)

Density 

1.2435 (rough estimate)

refractive index 

1.5100 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol

form 

Crystalline Mass or Crystals

color 

White to yellow

Water Solubility 

<0.01 g/L (20 ºC)

BRN 

878814

InChI

1S/C8H11NO3/c1-3-11-6-7(5-9)8(10)12-4-2/h6H,3-4H2,1-2H3/b7-6+

InChIKey

KTMGNAIGXYODKQ-VOTSOKGWSA-N

SMILES

CCO\C=C(/C#N)C(=O)OCC

LogP

1.376 at 25℃

CAS DataBase Reference

94-05-3(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester(94-05-3)

EPA Substance Registry System

2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester (94-05-3)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-42/43-41-37/38-22

Safety Statements 

26-37/39

RIDADR 

3276

WGK Germany 

1

Hazard Note 

Toxic

TSCA 

TSCA listed

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:2-Cyano-3-ethoxy-2-propenoic acid ethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl (ethoxymethylene)cyanoacetate Usage And Synthesis

Chemical Properties

white to light yellow crystalline solid

Uses

Ethyl Cyano(ethoxymethylene)acetate is an intermediate in the synthesis of anti-inflammatory agents with gastroprotective effect in rats.

Synthesis

a) General procedure for the preparation of ethyl 4-(2-cyano-2-ethoxycarbonylvinylamino)benzoate: triethyl orthoformate (33.3 mL, 0.2 mol) was mixed with ethyl cyanoacetate (21.3 mL, 0.2 mol) in acetic acid anhydride (80 mL), and the mixture was heated for 5 hr at 150-160 °C. Upon completion of the reaction, it was cooled to room temperature and the solvent was removed by distillation under reduced pressure to give ethyl 2-cyano-3-ethoxyacrylate as a yellow solid (28.5 g, 84% yield).

References

[1] Patent: US2006/4046, 2006, A1. Location in patent: Page/Page column 35
[2] Patent: WO2014/145986, 2014, A1. Location in patent: Paragraph 0274
[3] Arkivoc, 2017, vol. 2017, # 3, p. 73 - 86
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 3, p. 591 - 599
[5] Patent: US2012/277224, 2012, A1. Location in patent: Page/Page column 18

Ethyl (ethoxymethylene)cyanoacetate(94-05-3)Related Product Information

• Tris(trimethylsilyl)phosphate
• Ethyl 3-ethoxyacrylate
• POLY(ETHYL ACRYLATE)
• Ethyl acrylate
• Ethyl cellulose
• CHLOROETHANE
• Ethylbenzene
• Ethyl acetate
• Ethyl cyanoformate
• Ethyl methacrylate
• ETHYL 2-CYANOACRYLATE
• Ethyl isocyanoacetate
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Ethyl N-cyanoethanimideate
• Ethyl cyanoglyoxylate-2-oxime
• acetic acid, triethoxy-, ethyl ester
• Ethanol
• Cyanoacetic acid