2-BROMO-6-CHLORO-3-NITROPYRIDINE Chemical Properties

Boiling point:

277.2±35.0℃ (760 Torr)

Density 

1.936±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

121.5±25.9℃

storage temp. 

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

form 

solid

pka

-7.39±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C5H2BrClN2O2/c6-5-3(9(10)11)1-2-4(7)8-5/h1-2H

InChIKey

WISCKHBEOBONJA-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

2-BROMO-6-CHLORO-3-NITROPYRIDINE Usage And Synthesis

Synthesis

Example P3: Preparation of 2-bromo-6-chloro-3-nitropyridine. Under nitrogen protection, tert-butyl nitrite (990 mg, 9.60 mmol) was added batchwise to a stirred solution of 2-amino-6-chloro-3-nitropyridine (1.00 g, 5.76 mmol) and copper(II) bromide (1.56 g, 6.91 mmol) in acetonitrile (25 mL) at a reaction temperature of 65 °C. Stirring of the reaction mixture was continued for 30 minutes. After completion of the reaction, it was cooled to room temperature and the reaction mixture was partitioned between ethyl acetate and 2M aqueous hydrochloric acid solution. The organic layer was separated and dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: heptane-dichloromethane gradient) to afford the target product 2-bromo-3-nitro-6-chloropyridine (1.11 g, 81% yield) as a yellow solid. Mass spectrometry (EI) analysis showed m/z of 235.9/237.9 (relative abundance 78/100, [M]+).

References

[1] Patent: US2007/185154, 2007, A1. Location in patent: Page/Page column 10
[2] Patent: US2015/57260, 2015, A1. Location in patent: Paragraph 0575; 0576
[3] Patent: WO2015/25026, 2015, A1. Location in patent: Page/Page column 142
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 10151 - 10171

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