| Identification | Back Directory | [Name]
3-Amino-3-(3,4-dimethoxyphenyl)propionic acid | [CAS]
34841-09-3 | [Synonyms]
ZERO/001614
BAS 01906516
Oprea1_306666
Oprea1_623871
573426_ALDRICH
AG-205/40088415
3-AMINO-3-(3 4-DIMETHOXYPHENYL)PROPIONI&
3-ammonio-3-(3,4-dimethoxyphenyl)propanoate
3-ammonio-3-(3,4-dimethoxyphenyl)propionate
3-azaniumyl-3-(3,4-dimethoxyphenyl)propanoate
3-Amino-3-(3,4-dimethoxyphenyl)propionic acid
Benzenepropanoic acid, β-amino-3,4-dimethoxy-
3-aMino-3-(3,4-
diMethoxyphenyl)propionoic acid
3-Amino-3-(3,4-dimethoxyphenyl)propionicAcid>
Propanoic acid, 3-amino-3-(3,4-dimethoxyphenyl)-
3-Amino-3-(3,4-dimethoxyphenyl)propionic acid, beta-Amino-3,4-dimethoxyhydrocinnamic acid | [EINECS(EC#)]
202-110-6 | [Molecular Formula]
C11H15NO4 | [MDL Number]
MFCD00735172 | [MOL File]
34841-09-3.mol | [Molecular Weight]
225.24 |
| Chemical Properties | Back Directory | [Melting point ]
223 °C (dec.)(lit.)
| [Boiling point ]
379.7±42.0 °C(Predicted) | [density ]
1.212±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
powder to crystal | [pka]
3.73±0.10(Predicted) | [color ]
White to Almost white | [InChI]
1S/C11H15NO4/c1-15-9-4-3-7(5-10(9)16-2)8(12)6-11(13)14/h3-5,8H,6,12H2,1-2H3,(H,13,14) | [InChIKey]
FGCXSFRGPCUBPW-UHFFFAOYSA-N | [SMILES]
COc1ccc(cc1OC)C(N)CC(O)=O |
| Hazard Information | Back Directory | [Synthesis]
3,4-dimethoxybenzaldehyde (50 g, 0.33 mol) and ammonium acetate (50 g) were mixed in 95% ethanol (50 ml). The mixture was heated to 50 °C, followed by slow addition of malonic acid (63 g, 0.6 mol) and supplemented with 95% ethanol (25 ml). The reaction mixture was refluxed for 3 hours and then the reaction was continued at 80°C for 24 hours. Upon completion of the reaction, the precipitate was collected by filtration, washed with ethanol and recrystallized in 50% ethanol to afford 47.8 g of the target product 3-amino-3-(3,4-dimethoxyphenyl)propionic acid as a white solid (yield: 65%). The product was characterized by 1H NMR (300 MHz, D2O): δ 6.90-6.87 (m, 3H), 4.44-4.39 (t, 1H), 3.69 (s, 3H), 3.67 (s, 3H), 2.76-2.57 (m, 2H). Mass spectrum (EI) m/z: 226 (M++H). | [References]
[1] Chemical Communications, 2011, vol. 47, # 20, p. 5894 - 5896
[2] Patent: WO2010/16939, 2010, A1. Location in patent: Page/Page column 57
[3] Synlett, 2013, vol. 24, # 6, p. 733 - 736
[4] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 11, p. 1207 - 1212
[5] Tetrahedron Asymmetry, 2008, vol. 19, # 17, p. 2072 - 2077 |
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