| Identification | Back Directory | [Name]
Methyl 5-amino-2,4-difluorobenzoate | [CAS]
125568-73-2 | [Synonyms]
Methyl 5-amino-2,4-difluorobenzoate
Methyl 5-amino-2,4-difluorobenzoate USP/EP/BP
Benzoic acid, 5-amino-2,4-difluoro-, methyl ester
Benzoic acid, 5-amino-2,4-difluoro-, methyl ester (9CI) | [Molecular Formula]
C8H7F2NO2 | [MDL Number]
MFCD09396710 | [MOL File]
125568-73-2.mol | [Molecular Weight]
187.14 |
| Chemical Properties | Back Directory | [Boiling point ]
284.0±40.0 °C(Predicted) | [density ]
1.355±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
2.12±0.10(Predicted) | [Appearance]
Off-white to gray Solid |
| Hazard Information | Back Directory | [Uses]
Methyl 5-amino-2,4-difluorobenzoate is a carboxylic acid ester derivative used in pharmaceutical synthesis and experimental research.
| [Synthesis]
General procedure for the synthesis of methyl 5-amino-2,4-difluorobenzoate from methyl 2,4-difluoro-5-nitrobenzoate: to a solution of methyl 2,4-difluoro-5-nitrobenzoate (12.0 g, 0.06 mol, 1 eq.) in acetic acid (150 mL) and water was added iron powder (12.3 g, 0.22 mol, 4 eq.). The reaction mixture was heated to 40 °C and kept for 1.5 hours. After completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford methyl 5-amino-2,4-difluorobenzoate (10.0 g, 96% yield) as a brown solid.1H NMR (400 MHz, DMSO-d6) δppm: 7.27 (dd, J=9.98,7.42 Hz, 1H), 7.14 (t, J=10.99 Hz, 1H), 5.28 (s, 2H), 3.77 (s, 3H).ES-LCMS: m/z 189.0 (M+H). | [References]
[1] Patent: WO2009/75960, 2009, A1. Location in patent: Page/Page column 22
[2] Patent: WO2009/58919, 2009, A1. Location in patent: Page/Page column 23
[3] Patent: WO2009/58923, 2009, A1. Location in patent: Page/Page column 12
[4] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044 |
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