4-Morpholinobenzoic acid Chemical Properties

Melting point:

278 °C

Boiling point:

413.2±40.0 °C(Predicted)

Density 

1.253±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.70±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture & Light Sensitive

CAS DataBase Reference

7470-38-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934999090

4-Morpholinobenzoic acid Usage And Synthesis

Uses

4-(4-Morpholinyl)benzoic acid, is used as an intermediate in organic synthesis. The water based additive is used in a variety of applications as a heat-sealing and anti-blocking agent.

Definition

ChEBI: 4-morpholinobenzoic acid is a member of morpholines.

Synthesis

Example 1: Preparation of 4-(4-morpholinyl)benzoic acid by alkaline hydrolysis one-pot method using ethyl 4-fluorobenzoate and morpholine as raw materials. The procedure was as follows: ethyl 4-fluorobenzoate (3.5 g, 21 mmol) was mixed with morpholine (6.2 g, 70 mmol), and the reaction was heated at 130 °C for 12 hours until the ethyl 4-fluorobenzoate was completely converted. Subsequently, water (15 mL) and 20% NaOH solution (10 mL) were added to the reaction mixture and refluxing was continued for 3.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and acidified by adding 5% HCl solution with effective stirring. The precipitate was collected by filtration, washed with water and dried under vacuum at 60 °C to afford 4-morpholino benzoic acid (3.9 g) in 90% yield, melting point 275-277 °C. Mass spectrometric analysis showed the molecular ion peaks m/z 207 (100, M+).1H NMR (DMSO-d6) δ: 12.33 (br s, 1H), 7.78 (d, J=8.5 Hz. 2H), 6.95 (d, J=8.5 Hz, 2H), 3.72 (t, J=4.5 Hz, 2H), 3.23 (t, J=4.5 Hz, 2H).13C NMR (CDCl3) δ: 167.25, 153.90, 130.81, 119.91, 113.22, 65.87, 46.97.

References

[1] Patent: US2003/171581, 2003, A1

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