Ethyl 2-acetyl-3-(dimethylamino)acrylate Chemical Properties

Melting point:

41-44 °C(Solv: isopropyl ether (108-20-3))

Boiling point:

128°C 0,2mm

Density 

1.038±0.06 g/cm3(Predicted)

refractive index 

1.5330-1.5370

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

3.52±0.70(Predicted)

form 

Liquid

color 

Pale red

λmax

304nm(EtOH(95vol%))(lit.)

CAS DataBase Reference

51145-57-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34

Safety Statements 

26-36/37/39-45-23

RIDADR 

UN2735

HazardClass 

IRRITANT

HS Code 

2922500090

Ethyl 2-acetyl-3-(dimethylamino)acrylate Usage And Synthesis

Chemical Properties

Yellow Oil

Uses

Ethyl 2-Dimethylaminomethylene-3-oxobutanoate (cas# 51145-57-4) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate from ethyl acetoacetate and N,N-dimethylformamide dimethyl acetal was as follows: referring to Example 75, ethyl acetoacetate (79 mL, 0.62 mol) was added to N,N-dimethylformamide dimethyl acetal (100 mL, 0.68 mol) and the mixture was heated to reflux for 1 hour. Upon completion of the reaction, the excess acetal was removed by subtractive distillation, followed by subtractive distillation of the residue to afford the target product (Z)-ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate (85 g, 74% yield). The boiling point of the product was 125-130 °C (400 Pa).1H-NMR (CDCl3) δ: 1.33 (3H, t, J = 7.1 Hz), 2.33 (3H, s), 3.04 (6H, br s), 4.23 (2H, q, J = 7.1 Hz), 7.68 (1H, s).

References

[1] Patent: WO2006/73361, 2006, A1. Location in patent: Page/Page column 147
[2] Patent: US2007/244088, 2007, A1. Location in patent: Page/Page column 38
[3] Patent: US2008/9523, 2008, A1. Location in patent: Page/Page column 18; 19
[4] Patent: WO2008/4943, 2008, A1. Location in patent: Page/Page column 59
[5] Patent: WO2008/4942, 2008, A1. Location in patent: Page/Page column 56

Ethyl 2-acetyl-3-(dimethylamino)acrylate(51145-57-4)Related Product Information

• 3-Dimethylaminopropylamine
• Acetyl chloride
• Ethylparaben
• Acetylacetone
• Ethyl methacrylate
• Ethyl acetate
• Ethyl acrylate
• ETHYL 2-CYANOACRYLATE
• 2-Hydroxyethyl acrylate
• 2-Hydroxyethyl methacrylate
• Ethanol
• ISOXADIFEN-ETHYL
• POLY(ETHYL METHACRYLATE)
• POLY(ETHYL ACRYLATE)
• Ethyl cyanoacetate
• Trinexapac-ethyl
• N,N-Dimethyl-1,4-phenylenediamine
• Ethyl propiolate