| Identification | Back Directory | [Name]
N(alpha),N(alpha)-Dimethylalanine | [CAS]
2812-31-9 | [Synonyms]
N,N-dimethylalanine
L-Alanine, N,N-dimethyl-
N(alpha),N(alpha)-Dimethylalanine
(2S)-2-(dimethylamino)propanoic acid | [Molecular Formula]
C5H11NO2 | [MOL File]
2812-31-9.mol | [Molecular Weight]
117.15 |
| Chemical Properties | Back Directory | [Melting point ]
184-185 °C | [Boiling point ]
179.9±23.0 °C(Predicted) | [density ]
1.033±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
2.34±0.11(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
N,?N-?Dimethylalanine has been used as a reactant in the synthesis of Aplyronine A, a potent antitumor substance of marine origin. | [Definition]
ChEBI: A methyl-L-alanine in which both the amino hydrogens of L-alanine are replaced by methyl groups. | [Synthesis]
GENERAL STEPS: A mixture of L-alanine (2.5 g, 28 mmol), formaldehyde (8.4 g, 37 wt.%), 1N HCl (30 mL), and 10% Pd/C (500 mg) in methanol (30 mL) was subjected to a hydrogen atmosphere (50 psi), and the reaction was stirred for 5 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth (Celite) and the filtrate was concentrated under vacuum to afford an oily salt of (S)-2-(dimethylamino)propionic acid, which was solidified upon vacuum standing (4.4 g; yield higher than the theoretical value). The resulting product was used in subsequent steps without further purification.1H NMR (DMSO-d6, δ= 2.5, 500 MHz) data were as follows: δ 12.1 (br s, 1H), 4.06 (q, J = 7.4 Hz, 1H), 2.76 (s, 6H), 1.46 (d, J = 7.3 Hz, 3H). | [References]
[1] Tetrahedron Asymmetry, 2011, vol. 22, # 4, p. 464 - 467
[2] Organic Letters, 2013, vol. 15, # 12, p. 3118 - 3121
[3] Tetrahedron Letters, 2007, vol. 48, # 43, p. 7680 - 7682
[4] Synthesis, 2011, # 3, p. 490 - 496
[5] Bulletin of the Chemical Society of Japan, 1968, vol. 41, # 7, p. 1679 - 1681 |
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