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3-Chloro-2-hydroxy-5-nitropyridine

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3-Chloro-2-hydroxy-5-nitropyridine Basic information

Product Name:
3-Chloro-2-hydroxy-5-nitropyridine
Synonyms:
  • 3-CHLORO-5-NITRO-PYRIDIN-2-OL
  • 3-CHLORO-2-HYDROXY-5-NITROPYRIDINE
  • 2-HYDROXY-3-CHLORO-5-NITROPYRIDINE
  • 3-chloro-5-nitro-2-pyridinol
  • 3-Chloro-2-hydroxy-5-nitropyridine ,97%
  • 2-Hydroxy-3-Chloro-5-Methyl Pyridine
  • 3-Chloro-5-nitro-2-pyridone
  • 2(1H)-Pyridinone, 3-chloro-5-nitro-
CAS:
22353-38-4
MF:
C5H3ClN2O3
MW:
174.54
Product Categories:
  • Heterocycle-Pyridine series
  • Pyridine
  • Pyridines, Pyrimidines, Purines and Pteredines
  • Pyridines
Mol File:
22353-38-4.mol
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3-Chloro-2-hydroxy-5-nitropyridine Chemical Properties

Melting point:
187-189°
Boiling point:
286.1±40.0 °C(Predicted)
Density 
1.61±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
soluble in Methanol
form 
powder to crystal
pka
6.58±0.10(Predicted)
color 
White to Light yellow
InChI
InChI=1S/C5H3ClN2O3/c6-4-1-3(8(10)11)2-7-5(4)9/h1-2H,(H,7,9)
InChIKey
GTOXJMNILNYXLE-UHFFFAOYSA-N
SMILES
C1(=O)NC=C([N+]([O-])=O)C=C1Cl
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 2811 6.1 / PGIII
HazardClass 
IRRITANT
HS Code 
2933399990
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3-Chloro-2-hydroxy-5-nitropyridine Usage And Synthesis

Uses

3-Chloro-2-hydroxy-5-nitropyridine is a nitropyridine analogue. It is used as a raw material for organic synthesis or as a pharmaceutical intermediate compound.

Synthesis

5418-51-9

22353-38-4

2-Hydroxy-5-nitropyridine (200 g, 1.42 mol) was added in batches to 800 mL of concentrated hydrochloric acid under constant stirring and subsequently heated to 50 °C. Aqueous sodium chlorate solution (80.0 g, 0.75 mol dissolved in an appropriate amount of water) was added slowly and dropwise. The reaction temperature was maintained at 50 °C with continued stirring for 1 h. The reaction was cooled to 0 °C upon completion. The precipitated solid product was collected by filtration, washed thoroughly with cold water and dried to give 2-hydroxy-3-chloro-5-nitropyridine. Yield: 240 g, 1.37 mol (96.0% yield). Melting point: 195-197 °C. 1H NMR (300 MHz, DMSO-d6): δ 8.65 (d, 1H, J = 2.5 Hz), 8.36 (d, 1H, J = 2.5 Hz). 13C NMR (300 MHz, DMSO-d6): δ 153.40, 144.29, 143.59, 135.08. 130.44. mass spectrum (ES): m/z 175 ([M + H]+).

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 355 - 360
[2] Patent: WO2004/50637, 2004, A2. Location in patent: Page 66-67
[3] Synthesis, 1990, # 6, p. 499 - 501
[4] Patent: WO2014/115080, 2014, A1. Location in patent: Page/Page column 67; 68
[5] Patent: US6133253, 2000, A

3-Chloro-2-hydroxy-5-nitropyridine Preparation Products And Raw materials

Raw materials

3-Chloro-2-hydroxy-5-nitropyridineSupplier

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