| Identification | Back Directory | [Name]
2-BROMO-3-AMINOANISOLE | [CAS]
112970-44-2 | [Synonyms]
SA021377
2-Bromo-3-methoxyaniline
2-bromo-3-methoxybenzenamine
2-Bromo-3-methoxy-phenylamine
BenzenaMine, 2-broMo-3-Methoxy-
3-AMino-2-broMoanisole[2-BroMo-3-Methoxyaniline] | [Molecular Formula]
C7H8BrNO | [MDL Number]
MFCD07787450 | [MOL File]
112970-44-2.mol | [Molecular Weight]
202.05 |
| Chemical Properties | Back Directory | [Boiling point ]
273.1±20.0 °C(Predicted) | [density ]
1.531±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Off white/cream, fluffy/wooly flakes | [pka]
2.11±0.10(Predicted) | [Appearance]
Gray to black Solid |
| Hazard Information | Back Directory | [Uses]
2-Bromo-3-methoxyaniline can be used to treat epilepsy. | [Synthesis]
Step 1. Synthesis of 2-bromo-3-methoxyaniline (C23)
Iron powder (1.94 g, 34 mmol) was added to an ethanol solution (18 mL) of 2-bromo-1-methoxy-3-nitrobenzene (2.50 g, 10.77 mmol) followed by concentrated hydrochloric acid (1 mL). The reaction mixture was heated to reflux for 1.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, filtered through a pad of diatomaceous earth, and the filtrate was concentrated under vacuum to afford the title compound 2-bromo-3-methoxyaniline as a solid.
Yield: 2.57 g (10.77 mmol, 100%).
LCMS m/z: 202.1 [M + H]+.
1H NMR (400 MHz, CD3OD) δ: 3.77 (s, 3H), 6.30 (d, J = 8.0 Hz, 1H), 6.43 (d, J = 8.0 Hz, 1H), 6.98 (dd, J = 8.0, 8.0 Hz, 1H). | [References]
[1] Patent: US2012/252758, 2012, A1. Location in patent: Page/Page column 27
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9287 - 9295
[3] Patent: US2007/78147, 2007, A1. Location in patent: Page/Page column 67
[4] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 318
[5] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0441 |
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