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Home > Encyclopedia > 3-Amino-3-(4-methoxyphenyl)propionicacid

3-Amino-3-(4-methoxyphenyl)propionicacid

3-Amino-3-(4-methoxyphenyl)propionicacid structure

3-Amino-3-(4-methoxyphenyl)propionicacid 

structure
  • CAS No:

    5678-45-5

  • Formula:

    C10H13NO3

  • Chemical Name:

    3-Amino-3-(4-methoxyphenyl)propionicacid

  • Synonyms:

    RARECHEM AK HC T257;DL--(p-Methoxyphenyl)alanine;DL-BETA-(P-METHOXYPHENYL)ALANINE;3-(P-METHOXYPHENYL)-DL-BETA-ALANINE;Benzenepropanoicacid,β-aMino-4-Methoxy-;3-AMINO-3-(4-METHOXYPHENYL)PROPIONIC AC&;3-AMINO-3-(4-METHOXYPHENYL)PROPANOIC ACID;3-AMINO-3-(P-METHOXYPHENYL)PROPIONIC ACID;3-AMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID;3-Amino-3-(p-methoxyphenyl)propionic acid,98%

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

white to beige crystalline powder

3-Amino-3-(4-methoxyphenyl)propionicacid Basic Attributes

195.22

195.089539

2922509090

Characteristics

72.6

-1.4

1.2±0.1 g/cm3

230 °C (dec.)(lit.)

169.3±26.5 °C

1.559

Safety Information

IRRITANT

NONH for all modes of transport

3

36/37/38

37/39-26

Xi

Irritant

3-Amino-3-(4-methoxyphenyl)propionicacid Use and Manufacturing

To 150 mL of ethanol were added 28.5 g (0.21 mol) of 4-methoxybenzaldehyde, 21.8 g (0.21 mol) of malonic acid and 32.3 g (0.42 mol) of ammonium acetate, and the mixture was reacted while stirring under reflux (75 to 80°C) for 8 hours. After completion of the reaction, the obtained reaction mixture was stirred at room temperature for 20 hours, and filtered at room temperature to give 23.6 g of 3-amino-3-(4-methoxyphenyl)propionic acid (racemic mixtures) (isolation yield based on 4-methoxybenzaldehyde: 82.3percent) as white powder. Incidentally, physical properties of the 3-amino-3-(4-methoxyphenyl)propionic acid (racemic mixtures) were as follows. General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction. 4.1.1.1. 3-Amino-3-(4-methoxyphenyl)propanoic acid (A-1).Yield: 70percent, mp 236-8 °C, FT IR ( cm1): 3250-2900 (NH3), 3050 (CHsp2), 1613asym (CO), 1255 (C-O), 1156 (C-N). 1H NMR (500 MHz, DMSO‑d6): d 7.11 (d, 2H, C6H4), 6.77 (d, 2H, C6H4), 4.12 (q, 1H, CHN), 3.61 (s, 3H, OCH3), 2.32-2.41 (d, 2H, CHCH2). 13C NMR (126 MHz, DMSO‑d6): d 179.3, 161.8, 137.5, 129.7, 118.4, 59.8, 53.3, 49.1.

Computed Properties

Molecular Weight:195.21
XLogP3:-1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:195.08954328
Monoisotopic Mass:195.08954328
Topological Polar Surface Area:72.6
Heavy Atom Count:14
Complexity:188
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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