5-BROMO-2-HYDROXY-3-NITRO-4-PICOLINE Chemical Properties

Melting point:

240-243

Boiling point:

298.2±40.0 °C(Predicted)

Density 

1.84±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

6.34±0.10(Predicted)

color 

yellow

InChI

InChI=1S/C6H5BrN2O3/c1-3-4(7)2-8-6(10)5(3)9(11)12/h2H,1H3,(H,8,10)

InChIKey

QXPNHVCGSASGIX-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

2933399990

5-BROMO-2-HYDROXY-3-NITRO-4-PICOLINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-bromo-4-methyl-3-nitro-2(1H)-pyridinone from 2-amino-5-bromo-3-nitro-4-methylpyridine: to a solution of 5-bromo-4-methyl-3-nitro-pyridin-2-amine (28 g, 121 mmol) in water (900 ml) was slowly added concentrated sulfuric acid (28 ml) at 0 °C, followed by batchwise addition of sodium nitrite (20.91 g, 303 mmol). Water (100 ml) was added dropwise to control the reaction temperature. The reaction mixture was stirred at 0°C and then slowly warmed up to room temperature and kept for 2 hours. Subsequently, the reaction mixture was heated to 100 °C and maintained for 4 hours. Upon completion of the reaction, it was cooled to room temperature, the precipitated solid was collected by filtration, washed with water and dried to afford the target product 5-bromo-4-methyl-3-nitro-2(1H)-pyridinone as a light yellow solid (24.0 g, 85% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 12.97 (s, 1H), 8.01 (s, 1H), 2.21 (s, 3H); LC/MS analysis showed m/z 233 ([M+H]+).

References

[1] Patent: WO2014/125408, 2014, A2. Location in patent: Page/Page column 38

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