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4-BROMOPYRIDIN-2-OL

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CAS:36953-37-4
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4-BROMOPYRIDIN-2-OL Basic information
Product Name:4-BROMOPYRIDIN-2-OL
Synonyms:4-Iodoopyridin-2(1H)-one;4-BROMO-2-PYRIDINOL;4-BROMO-2-HYDROXYPYRIDINE;4-BROMOPYRIDIN-2-OL;4-Iodo-1H-pyridin-2-one;2-HYDROXY-4-BROMOPYRIDINE;4-IODOPYRIDIN-2(1H)-ONE;4-Iodo-1H-pyridin-2-one 97%
CAS:36953-37-4
MF:C5H4BrNO
MW:174
EINECS:
Product Categories:Heterocycle-Pyridine series;pharmacetical;Halides;Pyridines;Pyridine;Pyridine Series
Mol File:36953-37-4.mol
4-BROMOPYRIDIN-2-OL Structure
4-BROMOPYRIDIN-2-OL Chemical Properties
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
pka10.54±0.10(Predicted)
color White
InChIInChI=1S/C5H4BrNO/c6-4-1-2-7-5(8)3-4/h1-3H,(H,7,8)
InChIKeySSLMGOKTIUIZLY-UHFFFAOYSA-N
SMILESC1(=O)NC=CC(Br)=C1
CAS DataBase Reference36953-37-4(CAS DataBase Reference)
Safety Information
Risk Statements 36/38
Safety Statements 36
Hazard Note Harmful
HS Code 29333990
MSDS Information
4-BROMOPYRIDIN-2-OL Usage And Synthesis
Uses4-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
4-Bromo-2-methoxypyridine

100367-39-3

4-BROMOPYRIDIN-2-OL

36953-37-4

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
4-BROMOPYRIDIN-2-OL Preparation Products And Raw materials
Raw materials2-(Benzyloxy)-4-bromopyridine-->2-Chloro-4-bromopyridine-->4-Bromo-2-methoxypyridine-->Water-->Hydrochloric acid-->Sodium hydroxide-->1,4-Dioxane
Tag:4-BROMOPYRIDIN-2-OL(36953-37-4) Related Product Information
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