3-Amino-3-(4-fluorophenyl)propanoic acid Chemical Properties

Melting point:

224-228 °C (dec.) (lit.)

Boiling point:

308.8±32.0 °C(Predicted)

Density 

1.289±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.66±0.10(Predicted)

color 

White to Almost white

optical activity

0.20°(C=0.55g/100mL, HCL, 20°C, 589nm)

BRN 

3258498

InChIKey

CPGFMWPQXUXQRX-UHFFFAOYSA-N

CAS DataBase Reference

325-89-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29225090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Amino-3-(4-fluorophenyl)propanoic acid Usage And Synthesis

Uses

3-Amino-3-(4-fluorophenyl)propionic acid is a carboxylic acid derivative that can be used as a pharmaceutical intermediate for pharmaceutical synthesis and experimental research.

Chemical Properties

White powder

Synthesis

To a 150 mL round bottom flask was added 30.5 g (0.25 mol) of 4-fluorobenzaldehyde, 25.6 g (0.25 mol) of malonic acid and 28.4 g (0.37 mol) of ammonium acetate dissolved in ethanol. The reaction mixture was heated to 75-80°C and the reaction was stirred under reflux conditions for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and stirring was continued for 1 hour. Subsequently, the precipitate was collected by filtration and dried under reduced pressure at 45°C to give 28.3 g of 3-amino-3-(4-fluorophenyl)propionic acid (racemic mixture) in 62.8% yield (calculated based on 4-fluorobenzaldehyde), the product was a white powder. The physical properties of 3-amino-3-(4-fluorophenyl)propionic acid (racemic mixture) were as follows: 1H-NMR (δ, ppm, D2O): 2.49 (dd, 1H, J = 17.1, 6.8 Hz), 2.62 (dd, 1H, J = 17.1, 7.8 Hz), 4.20 (dd, 1H, J = 7.8, 6.8 Hz), 6.58-6.62 (m, 2H), 6.88-6.91 (m, 1H) 13C-NMR (δ, ppm, D2O): 37.1, 50.5, 115.5, 115.8, 128.9, 130.4, 172.6 MS (EI) m/z: 183 (M+) MS (CI, i-C4H10) m/z: 184 (MH+)

References

[1] Chemical Communications, 2011, vol. 47, # 20, p. 5894 - 5896
[2] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 260 - 264
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1938 - 1950
[4] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268
[5] European Journal of Medicinal Chemistry, 1992, vol. 27, # 9, p. 961 - 965

3-Amino-3-(4-fluorophenyl)propanoic acid(325-89-3)Related Product Information

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• (S)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID
• BOC-(S)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID
• FMOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID
• (R)-3-amino-3-(4-fluorophenyl)propanoic acid
• BOC-(R)-2-AMINO-3-(4'-FLUOROPHENYL)PROPANOIC ACID
• (R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID
• 3-[(TERT-BUTOXYCARBONYL)AMINO]-3-(3-FLUOROPHENYL)PROPANOIC ACID
• rac-(R*)-2-Amino-3-(4-fluorophenyl)propanoic acid,2-amino-3-(4-fluorophenyl)propanoic acid
• 3-[(TERT-BUTOXYCARBONYL)AMINO]-3-(4-FLUOROPHENYL)PROPANOIC ACID