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

pka

10.54±0.10(Predicted)

form 

Crystalline Powder

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)

Safety Information

Risk Statements 

36/38

Safety Statements 

36

Hazard Note 

Harmful

HS Code 

29333990

4-BROMOPYRIDIN-2-OL Usage And Synthesis

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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