3-Amino-3-(4-methoxyphenyl)propionic acid Chemical Properties

Melting point:

230 °C (dec.)(lit.)

Boiling point:

331.88°C (rough estimate)

Density 

1.1926 (rough estimate)

refractive index 

1.5150 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder to crystal

pka

3.74±0.10(Predicted)

color 

White to Almost white

CAS DataBase Reference

5678-45-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2922500090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-Amino-3-(4-methoxyphenyl)propionic acid Usage And Synthesis

Chemical Properties

white to beige crystalline powder

Synthesis

To a 150 mL round bottom flask was added 28.5 g (0.21 mol) of p-methoxybenzaldehyde, 21.8 g (0.21 mol) of malonic acid and 32.3 g (0.42 mol) of ammonium acetate dissolved in 150 mL of ethanol. The reaction mixture was heated to 75-80°C and the reaction was stirred under reflux conditions for 8 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and stirring was continued for 20 hours. Subsequently, a white solid was collected by filtration to afford 23.6 g of 3-amino-3-(4-methoxyphenyl)propionic acid (racemic mixture) in 82.3% yield (based on p-methoxybenzaldehyde). The product was a white powder and its physical properties were as follows: 1H-NMR (δ, ppm, D2O): 2.50 (dd, 1H, J = 17.1, 6.8 Hz), 2.65 (dd, 1H, J = 17.1, 7.8 Hz), 3.24 (s, 3H), 6.46 (s, 1H), 6.48 (s, 1H), 6.86 (s, 1H), 6.88 (s, 1H); 13C-NMR (δ, ppm, D2O): 37.1, 50.7, 55.1, 114.3, 126.9, 128.2, 159.1, 172.7; MS (EI) m/z: 195 (M+); MS (CI, i-C4H10) m/z: 196 (MH+).

References

[1] Patent: EP1621529, 2006, A1. Location in patent: Page/Page column 40
[2] Chemical Communications, 2011, vol. 47, # 20, p. 5894 - 5896
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1938 - 1950
[4] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 395 - 406
[5] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268

3-Amino-3-(4-methoxyphenyl)propionic acid(5678-45-5)Related Product Information

• 3-Amino-3-phenylpropionic acid
• (Trifluoromethoxy)benzene
• Propionic acid
• 6-Aminocaproic acid
• Glycine
• 4-Methoxyphenylacetone
• Phenprobamate
• β-Alanine
• D-Alanine
• EC 2.6.1.2
• Anisole
• p-Anisaldehyde
• 1-Isoquinolineacetic acid, 1,2,3,4-tetrahydro-6,7-dimethoxy-, ethyl ester
• (S)-3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID
• (S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID
• 3-(BOC-AMINO)-3-(3-METHOXYPHENYL)PROPIONIC ACID
• (R)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID
• 3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID