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| | ETHYL 3-(N-METHYLAMINO) PROPIONATE Basic information |
| Product Name: | ETHYL 3-(N-METHYLAMINO) PROPIONATE | | Synonyms: | ETHYL 3-(N-METHYLAMINO) PROPIONATE;Ethyl N-methyl-beta-alaninate;.beta.-Alanine, N-methyl-, ethyl ester;3-(Methylamino)propionic acid ethyl ester;3-methylaminopropanoic acid ethyl ester;3-methylaminopropionic acid ethyl ester;N-Methyl-b-alanine ethyl ester;114537 | | CAS: | 2213-08-3 | | MF: | C6H13NO2 | | MW: | 131.17 | | EINECS: | | | Product Categories: | | | Mol File: | 2213-08-3.mol |  |
| | 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 |
| | 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 |
| | ETHYL 3-(N-METHYLAMINO) PROPIONATE Preparation Products And Raw materials |
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