3-AMINO-3-(4-CHLOROPHENYL)PROPIONIC ACID Chemical Properties

Melting point:

223 °C (dec.)(lit.)

Boiling point:

345.8±32.0 °C(Predicted)

Density 

1.2409 (rough estimate)

refractive index 

1.5790 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

3.62±0.10(Predicted)

form 

Powder

color 

Off-white

BRN 

2365902

CAS DataBase Reference

19947-39-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

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

3-AMINO-3-(4-CHLOROPHENYL)PROPIONIC ACID Usage And Synthesis

Chemical Properties

off-white powder

Synthesis

To 25 mL of ethanol were sequentially added 5.00 g (35.6 mmol) of 4-chlorobenzaldehyde, 3.70 g (35.6 mmol) of malonic acid and 4.10 g (53.2 mmol) of ammonium acetate, and the reaction mixture was stirred at reflux for 8 hr at 75 to 80°C. The reaction was carried out by stirring the mixture for 1 hr at room temperature. After completion of the reaction, the mixture was continued to be stirred at room temperature for 1 h. Subsequent filtration afforded 5.9 g of 3-amino-3-(4-chlorophenyl)propionic acid (racemic mixture) as a white powder (82.3% isolated yield based on 4-chlorobenzaldehyde). The physical properties of the compound were as follows: 1H-NMR (δ, ppm, D2O): 2.93 (dd, 1H, J = 17.1, 6.8 Hz), 3.04 (dd, 1H, J = 17.1, 7.8 Hz), 4.63 (dd, 1H, J = 7.8, 6.8 Hz), 7.22 (s, 1H), 7.24 (s, 1H), 7.47 (s, 1H), 7.49 (s, 1H); 13C-NMR (δ, ppm, D2O): 40.4, 53.9, 126.0, 131.9, 135.3, 137.1, 175.9; MS (EI) m/z: 199 (M+); MS (CI, i-C4H10) m/z: 200 (MH+).

References

[1] Patent: EP1621529, 2006, A1. Location in patent: Page/Page column 31
[2] Preparative Biochemistry and Biotechnology, 2013, vol. 43, # 2, p. 207 - 216
[3] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268
[4] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
[5] Heterocycles, 1989, vol. 28, # 2, p. 1015 - 1035

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