| Identification | Back Directory | [Name]
3-BROMO-4-METHOXYANILINE | [CAS]
19056-41-8 | [Synonyms]
4-Amino-2-bromoanisole
3-BROMO-4-METHOXYANILINE
3-Bromo-4-methoxyaniline >
Benzenamine, 3-bromo-4-methoxy-
4-Amino-2-bromoanisole, 3-Bromo-p-anisidine
3-BROMO-4-METHOXYANILINE ISO 9001：2015 REACH | [Molecular Formula]
C7H8BrNO | [MDL Number]
MFCD04094339 | [MOL File]
19056-41-8.mol | [Molecular Weight]
202.05 |
| Chemical Properties | Back Directory | [Melting point ]
62 °C | [Boiling point ]
282.2±20.0 °C(Predicted) | [density ]
1.531±0.06 g/cm3(Predicted) | [storage temp. ]
Room temperature. | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
4.13±0.10(Predicted) | [color ]
White to Brown | [InChIKey]
NMUFTXMBONJQTC-UHFFFAOYSA-N | [CAS DataBase Reference]
19056-41-8 |
| Hazard Information | Back Directory | [Uses]
3-Bromo-4-methoxyaniline is an intermediate used to prepare triazole analogs of combretastatin A-4 as cytotoxic agents and inhibitors of tubulin. It is also used in the synthesis of (1,2,4-oxadiazolyl)biphenylcarbonyltetrahydrospiro[furo]indolepiperidine (SB-224289) as selective 5-HT1B receptor inverse agonist. | [Synthesis]
General procedure for the synthesis of 3-bromo-4-methoxyaniline from 2-bromo-4-nitroanisole: 2-bromo-4-nitroanisole (0.1 g, 0.43 mmol) was suspended in unstabilized 57% hydriodic acid (1.3 mL), and the reaction was heated for 5 hr at 90 °C. After completion of the reaction, the reaction mixture was cooled, diluted with ethyl acetate (5 mL) and washed sequentially with saturated aqueous sodium thiosulfate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was further purified by silica gel column chromatography to afford 3-bromo-4-methoxyaniline (0.07 g, 80% yield). | [References]
[1] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[2] Patent: WO2011/98776, 2011, A1. Location in patent: Page/Page column 60
[3] Patent: US2013/53372, 2013, A1. Location in patent: Paragraph 0584; 0585
[4] Patent: US2007/123515, 2007, A1. Location in patent: Page/Page column 24
[5] Justus Liebigs Annalen der Chemie, 1883, vol. 217, p. 44 |
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