Ethyl 3-(benzylamino)propanoate Chemical Properties

Boiling point:

150 °C

Density 

1.017 g/mL at 25 °C

refractive index 

1.503

Flash point:

150°C/0.2mm

storage temp. 

-20°C

pka

8.57±0.19(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

InChI

InChI=1S/C12H17NO2/c1-2-15-12(14)8-9-13-10-11-6-4-3-5-7-11/h3-7,13H,2,8-10H2,1H3

InChIKey

HCTJHQFFNDLDPF-UHFFFAOYSA-N

SMILES

C(C1C=CC=CC=1)NCCC(=O)OCC

CAS DataBase Reference

23583-21-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/38-52/53-22

Safety Statements 

26-36/37/39-61

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:ALFA

Ethyl 3-(benzylamino)propanoate Usage And Synthesis

Chemical Properties

Solid

Uses

N-Benzyl-β-alanine Ethyl Ester is used as a reagent in organic synthesis including that of dipivaloyloxyphenyl aminopropionate β-agonist prodrugs which are used in the treatment of psoriasis. It is also used in the synthesis of N,N''-dithiobis(N-benzyl-β-alanine) dethyl ester, which is an important intermediate of insecticide OK-135, and in synthesis of spiropiperidine-based orexin-2 receptor (OX2R) antagonists.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

GENERAL METHODS: Benzylamine (7.5 mmol) was mixed with ethyl acrylate (5 mmol) in a molar ratio of 1.5:1 under acidic alumina (1 g, 200 mol%) as a catalyst and the reaction was carried out by refluxing under stirring. The reaction was heated by oil bath and the progress of the reaction was monitored by thin layer chromatography (TLC) and gas chromatography (GC) until completion. After completion of the reaction, it was cooled to room temperature and the catalyst was removed by filtration through filter paper. The catalyst was rinsed with a solvent mixture of ethyl acetate/hexane and the filtrate was subsequently concentrated by rotary evaporation. The crude product was purified by silica gel column chromatography, using hexane/ethyl acetate as eluent of choice. For aliphatic amine derivatives, a hexane/ethyl acetate ratio of 7:3, 6:4, or 5:5 was typically used to elute the monoadducts, while for aromatic compounds, a hexane/ethyl acetate ratio of 8:2 was used. The yields of the purified products were recorded and infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) analyses were performed to confirm the product structures.

References

[1] Molecules, 2016, vol. 21, # 6,
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 971
[3] New Journal of Chemistry, 2004, vol. 28, # 2, p. 183 - 184
[4] Synthetic Communications, 2013, vol. 43, # 5, p. 758 - 767

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