ETHYL 3-(N-METHYLAMINO) PROPIONATE Chemical Properties

Boiling point:

242.49°C (rough estimate)

Density 

1.0070

refractive index 

1.4443 (estimate)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Oil

pka

9.55±0.10(Predicted)

color 

Colourless

InChI

InChI=1S/C6H13NO2/c1-3-9-6(8)4-5-7-2/h7H,3-5H2,1-2H3

InChIKey

XVIJMHJTEHBUJI-UHFFFAOYSA-N

SMILES

C(=O)(OCC)CCNC

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2922498590

ETHYL 3-(N-METHYLAMINO) PROPIONATE Usage And Synthesis

Uses

Ethyl N-Methyl-beta-alaninate is an intermediate in the synthesis of Tolafentrine (T531000), which is a dual-selective phosphodiesterase 3/4 inhibitor used in chronic experimental pulmonary hypertension.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2124, 1949 DOI: 10.1021/ja01174a061

Synthesis

1. cool 33% methylamine ethanol solution (100 mL, 805 mmol) in an ice bath at 0 °C. 2. Ethyl acrylate (11.0 mL, 10.1 g, 101 mmol) was added slowly, keeping the reaction temperature at 0 °C with continuous stirring for 2 hours. 3. Gradually warm the reaction mixture to room temperature and continue stirring for 15 minutes. 4. All volatiles were removed by distillation under reduced pressure. 5. The resulting residue (ethyl 3-(methylamino)propionate crude, 11.2 g) was used directly in the subsequent reaction without further purification.

References

[1] Monatshefte fur Chemie, 2011, vol. 142, # 10, p. 1055 - 1059
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 1739 - 1745
[3] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 87 - 91
[4] Liebigs Annalen der Chemie, 1980, # 9, p. 1438 - 1447
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 2129

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