| Identification | More | [Name]
3-Bromo-4-hydroxypyridine | [CAS]
36953-41-0 | [Synonyms]
3-BROMO-4-HYDROXYPYRIDINE
3-BROMO-4-PYRIDINOL
4-HYDROXY-3-BROMOPYRIDINE
3-BROMO-4-HYDROXYPYRIDINE 97%
3-Bromopyridin-4-ol | [Molecular Formula]
C5H4BrNO | [MDL Number]
MFCD01646107 | [Molecular Weight]
174 | [MOL File]
36953-41-0.mol |
| Hazard Information | Back Directory | [Uses]
3-Bromo-4-hydroxypyridine is a pyrrole that can be used in cancer treatment. It inhibits the growth of cancer cells by binding to MKN-45 on the cell surface, thereby preventing it from binding to other proteins and triggering cell proliferation. | [Synthesis]
3-Bromo-4-hydroxypyridine is synthesized from 3-bromo-5 hydroxypyridine by reacting it with ammonia or methylamine.
Concentrated sulfuric acid (85.0mL) and the 3-bromo-4-aminopyridine (113.0g, 0.65mol) were added successively to the distilled water (550.0mL) at 0°C, and then NaNO2 (63.1g, 0.91mol) aqueous solution (130.0mL) was added drop-wise to maintain the temperature between 0 and 5°C. After stirring at r. t. for 1h, the reaction mixture was heated at 95°C for a further 0.5h. Upon cooling to below 0°C, the mixture was alkalized to pH 6 with saturated sodium hydroxide solution, washed with ethyl acetate (200mL×3) and brine (200mL), dried over anhydrous Na2SO4, filtered and concentrated to yield 3-Bromo-4-hydroxypyridine as a yellow solid (75.1g, 66.2percent).
| [References]
[1] Patent: US2010/93720, 2010, A1. Location in patent: Page/Page column 58
[2] Synlett, 2003, # 11, p. 1678 - 1682
[3] Patent: WO2012/148808, 2012, A1. Location in patent: Page/Page column 51 |
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