3-(1H-Pyrrol-2-yl)propanoic acid Chemical Properties

Melting point:

85-86 °C

Boiling point:

130-135 °C(Press: 0.5 Torr)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.51±0.10(Predicted)

Appearance

Yellow to brown Solid

3-(1H-Pyrrol-2-yl)propanoic acid Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-(1H-pyrrol-2-yl)propionic acid from ethyl 3-(1H-pyrrol-2-yl)propionate: sodium hydroxide (3.8 g, 95.00 mmol) was added batchwise to ethyl 3-(1H-pyrrol-2-yl)propionate (8 g, 47.85 mmol) in a mixed solution of ethanol/water (80 mL/40 mL) at 0-5 °C. . The reaction temperature was maintained at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction process was monitored by LCMS. After completion of the reaction, the reaction solution was concentrated under reduced pressure. Subsequently, the pH of the concentrate was adjusted to 3-4 with 10% hydrochloric acid solution and then extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and finally concentrated under reduced pressure to give 7 g (95% yield) of 3-(1H-pyrrol-2-yl)propionic acid as a white solid.

References

[1] Patent: WO2009/139834, 2009, A1. Location in patent: Page/Page column 161
[2] European Journal of Organic Chemistry, 2010, # 19, p. 3611 - 3620
[3] Tetrahedron, 2004, vol. 60, # 7, p. 1505 - 1511

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