| Identification | More | [Name]
4-BROMOPYRIDIN-2-OL | [CAS]
36953-37-4 | [Synonyms]
4-BROMO-2-HYDROXYPYRIDINE
4-BROMO-2-PYRIDINOL
4-BROMOPYRIDIN-2-OL
4-Iodoopyridin-2(1H)-one
4-Iodo-1H-pyridin-2-one
2-HYDROXY-4-BROMOPYRIDINE
4-IODOPYRIDIN-2(1H)-ONE
4-Iodo-1H-pyridin-2-one 97%
4-BROMO-2-HYDROXYPYRIDINE 97%
4-CYANO-3,5-DIFLUOROANISOLE | [Molecular Formula]
C5H4BrNO | [MDL Number]
MFCD00234041 | [Molecular Weight]
174 | [MOL File]
36953-37-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
186 °C | [Boiling point ]
305.9±42.0 °C(Predicted) | [density ]
1.776±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Powder | [pka]
10.54±0.10(Predicted) | [color ]
White | [InChI]
InChI=1S/C5H4BrNO/c6-4-1-2-7-5(8)3-4/h1-3H,(H,7,8) | [InChIKey]
SSLMGOKTIUIZLY-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=CC(Br)=C1 | [CAS DataBase Reference]
36953-37-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
4-Bromo-2-hydroxypyridine is used as a reagent to synthesize trans-3,4’-bispyridinylethylenes, compounds that act as inhibitors of protein kinase B that are used to treat cancer. | [Synthesis]
General procedure for the synthesis of 4-bromo-2-hydroxypyridine from 4-bromo-2-methoxypyridine:
Step a: Preparation of 4-bromopyridin-2(1H)-one; To a solution of 1,4-dioxane (26 mL) of 4-bromo-2-methoxypyridine (1.0 g, 5.3 mmol) was added an aqueous 4M HCl solution (13 mL). The reaction mixture was heated at 90 °C for 5 h, followed by heating at 50 °C overnight. Upon completion of the reaction, it was neutralized to pH 8-9 with 1N NaOH solution and extracted with ethyl acetate. The organic phase was dried with anhydrous MgSO4 and concentrated to give 4-bromopyridin-2(1H)-one as a white solid (490 mg, 53% yield). The aqueous phase was concentrated and the residue was stirred with dichloromethane and filtered. The filtrate was concentrated to give additional 4-bromopyridin-2(1H)-one (320 mg, 35% yield).ESI-MS m/z calculated value 173.0, measured value 174.3 (M+1)+. Retention time 0.32 min. 1H NMR (400 MHz, DMSO-d6) δ 11.87 (s, 1H), 7.36 (d, J=7.0 Hz, 1H), 6.64 (d, J=2.0 Hz, 1H), 6.37 (dd, J=2.0,7.0 Hz, 1H). | [References]
[1] Patent: WO2008/141119, 2008, A2. Location in patent: Page/Page column 97
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 21, p. 6262 - 6267 |
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