5-Bromo-2-methyl-3-nitropyridine Chemical Properties

Melting point:

38.0 to 42.0 °C

Boiling point:

253 °C

Density 

1.709

Flash point:

107 °C

storage temp. 

Inert atmosphere,Room Temperature

pka

-0.44±0.20(Predicted)

form 

powder to crystal

color 

Light yellow to Amber to Dark green

InChI

InChI=1S/C6H5BrN2O2/c1-4-6(9(10)11)2-5(7)3-8-4/h2-3H,1H3

InChIKey

FZZLWWNOYMHSIS-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

5-Bromo-2-methyl-3-nitropyridine Usage And Synthesis

Uses

5-Bromo-2-methyl-3-nitropyridine is used as a reactant in the synthesis of MLN0905, a potent and orally bioavailable inhibitor of Polo-like kinase 1 (PLK1).

Synthesis

Step 2 - Synthesis of 5-bromo-2-methyl-3-nitropyridine Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (1.2 g, 3.3 mmol) was dissolved in 7.0 N HCl (10 mL). The mixture was heated to reflux for 5 hours. After completion of the reaction, it was cooled to room temperature and extracted with dichloromethane: methanol (10:1, v/v). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using petroleum ether: ethyl acetate (4:1, v/v) as eluent to afford 5-bromo-2-methyl-3-nitropyridine (0.7 g, yield: 89.7%). 1H-NMR (CDCl3, 400 MHz) δ 8.76 (s, 1H), 8.40 (s, 1H), 2.80 (s, 3H).

References

[1] Patent: US2008/194552, 2008, A1. Location in patent: Page/Page column 40
[2] Patent: WO2010/68292, 2010, A1. Location in patent: Page/Page column 78
[3] Patent: WO2013/33899, 2013, A1. Location in patent: Page/Page column 39
[4] Patent: WO2013/34048, 2013, A1. Location in patent: Page/Page column 46; 47
[5] Patent: WO2012/88411, 2012, A1. Location in patent: Page/Page column 64

5-Bromo-2-methyl-3-nitropyridine(911434-05-4)Related Product Information

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• 5-BROMO-3-NITROPYRIDINE-2-CARBOXYLIC ACID
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• (5-BROMO-3-NITRO-PYRIDIN-2-YL)-ACETONITRILE
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• (5-BROMO-3-NITRO-PYRIDIN-2-YL)-ACETIC ACID