2,4-DIBROMO-5-NITROPYRIDINE Chemical Properties

Melting point:

99 °C

Boiling point:

292.0±35.0 °C(Predicted)

Density 

2?+-.0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-2.18±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C5H2Br2N2O2/c6-3-1-5(7)8-2-4(3)9(10)11/h1-2H

InChIKey

RZZGFCFQBVRQSX-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C([N+]([O-])=O)C(Br)=C1

CAS DataBase Reference

4487-57-4

Safety Information

HS Code 

2933399990

2,4-DIBROMO-5-NITROPYRIDINE Usage And Synthesis

Uses

2,4-Dibromo-5-nitropyridine is a tri-substituted pyridine derivative used in the preparation of AKT kinase inhibitors and antihypertensive agents.

Synthesis

The general procedure for the synthesis of 2,4-dibromo-5-nitropyridine from 4-methoxy-5-nitropyridin-2(1H)-one is as follows: step 2. Phosphoribromide (5.73 g, 20 mmol) was slowly added to a suspension of the product of step 1 (1.70 g, 10 mmol) in acetonitrile (20 mL) at room temperature. Subsequently, the reaction mixture was heated to reflux and maintained for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and carefully poured into ice water and left to stratify. The aqueous layer was extracted with ethyl acetate (EtOAc) and the organic phases were combined. The organic phase was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give the title compound 2,4-dibromo-5-nitropyridine (2.1 g, 75% yield) as a dark solid.

References

[1] Patent: WO2005/37197, 2005, A2. Location in patent: Page/Page column 94
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1508 - 1511
[3] Patent: WO2006/113837, 2006, A2. Location in patent: Page/Page column 36; 63
[4] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 1, p. 42 - 46

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