| Identification | Back Directory | [Name]
1-Amino-2-methylpropan-2-ol | [CAS]
2854-16-2 | [Synonyms]
EOS-60808
NSC 17697
1-amino-2-methyL
TIANFU-CHEM 2854-16-2
2-Hydroxyisobutylamine
1,1-Dimethylethanolamine
-Amino-2-methylpropan-2-ol
2-Amino-a,a-dimethylethanol
1-Amino-2-methylpropan-2-ol
1-Amino-2-methyl-2-propanol
3-Amino-2-methyl-2-propanol
2-Propanol, l-aMino-2-Methyl
2-Methyl-2-hydroxypropylamine
1-azanyl-2-methyl-propan-2-ol
Amino-2-methyl-2-propanol, 1-
2-Propanol, 1-aMino-2-Methyl-
1-Amino-2-methyl-2-propanol >
2-Hydroxy-2-methyl-1-propylamine
1-Amino-2-methylpropan-2-ol-13C3
1,1-Dimethylethanolamine 1-amino-2-methylpropan-2-ol
2-Hydroxy-2-methylpropylamine, 1-Amino-2-hydroxy-2-methylpropane | [Molecular Formula]
C4H11NO | [MDL Number]
MFCD01697283 | [MOL File]
2854-16-2.mol | [Molecular Weight]
89.14 |
| Chemical Properties | Back Directory | [Melting point ]
8.72°C (estimate) | [Boiling point ]
151°C(lit.) | [density ]
1.915 g/mL at 25 °C | [refractive index ]
n20/D1.448 | [Fp ]
73℃ | [storage temp. ]
2-8°C | [solubility ]
Chloroform, Ethyl Acetate (Slightly) | [form ]
Oil | [pka]
12.99±0.50(Predicted) | [color ]
Clear Colourless | [InChI]
InChI=1S/C4H11NO/c1-4(2,6)3-5/h6H,3,5H2,1-2H3 | [InChIKey]
LXQMHOKEXZETKB-UHFFFAOYSA-N | [SMILES]
C(N)C(C)(O)C | [CAS DataBase Reference]
2854-16-2 | [NIST Chemistry Reference]
1-Amino-2-methyl-2-propanol(2854-16-2) |
| Hazard Information | Back Directory | [Chemical Properties]
Pale yellow liquid | [Uses]
3-Amino-2-methyl-2-propanol, is a versatile intermediate used for the synthesis of more complex compounds, including inhibitors. It is an intermediate in the preparation of metabolites of Darunavir (D193500), such as (A581405). | [Synthesis]
The general procedure for the synthesis of 1-amino-2-methyl-2-propanol from acetone cyanohydrin is as follows:
Step A: Synthesis of 1-amino-2-methyl-2-propanol [Chem.17]
To a tetrahydrofuran (180 mL) suspension of lithium aluminum hydride (6.08 g, 160 mmol), a tetrahydrofuran (20 mL) solution of acetone cyanohydrin (7.32 mL, 80.0 mmol) was slowly added dropwise over a controlled period of 15 min at 0 °C. The reaction mixture was then refluxed for 4 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched with sodium sulfate decahydrate and potassium fluoride. After continued stirring at 35°C for 30 minutes, the mixture was filtered through a diatomaceous earth pad. The filtrate was concentrated in vacuum to give the oily product 1-amino-2-methyl-2-propanol (3.98 g, 56% yield).
[0229] 1H-NMR (300 MHz, CDCl3) δ: 2.60 (s, 2H), 1.69 (s, 6H), no peaks for OH and NH2 were observed. | [References]
[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4336 - 4351
[2] Patent: WO2010/84767, 2010, A1. Location in patent: Page/Page column 50-51
[3] Tetrahedron Letters, 1996, vol. 37, # 40, p. 7319 - 7322
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 18, p. 3347 - 3359
[5] Patent: EP1591446, 2005, A1. Location in patent: Page/Page column 96 |
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