ChemicalBook--->CAS DataBase List--->22353-38-4

22353-38-4

22353-38-4 Structure

22353-38-4 Structure
IdentificationBack Directory
[Name]

3-CHLORO-2-HYDROXY-5-NITROPYRIDINE
[CAS]

22353-38-4
[Synonyms]

3-Chloro-5-nitro-2-pyridone
3-chloro-5-nitro-2-pyridinol
3-CHLORO-5-NITRO-PYRIDIN-2-OL
3-Chloro-2-Hydroxy-5-Picoline
3-CHLORO-2-HYDROXY-5-NITROPYRIDINE
2-HYDROXY-3-CHLORO-5-NITROPYRIDINE
2(1H)-Pyridinone, 3-chloro-5-nitro-
2-Hydroxy-3-Chloro-5-Methyl Pyridine
3-Chloro-2-hydroxy-5-nitropyridine ,97%
3-CHLORO-2-HYDROXY-5-NITROPYRIDINE ISO 9001:2015 REACH
[Molecular Formula]

C5H3ClN2O3
[MDL Number]

MFCD06656618
[MOL File]

22353-38-4.mol
[Molecular Weight]

174.54
Chemical PropertiesBack Directory
[Melting point ]

187-189°
[Boiling point ]

286.1±40.0 °C(Predicted)
[density ]

1.61±0.1 g/cm3(Predicted)
[storage temp. ]

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
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

45
[RIDADR ]

UN 2811 6.1 / PGIII
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

N,N-Dimethylformamide-->N-Chlorosuccinimide-->2-Hydroxy-5-nitropyridine-->2,3-Dichloro-5-nitropyridine-->2-Amino-3-chloro-5-nitropyridine-->Salicylhydroxamic acid-->2-Amino-5-nitropyridine
[Preparation Products]

2-Benzoxazolinone-->5-Amino-2,3-dichloropyridine
Hazard InformationBack Directory
[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]

2-Hydroxy-5-nitropyridine

5418-51-9

3-Chloro-2-hydroxy-5-nitropyridine

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
Spectrum DetailBack Directory
[Spectrum Detail]

3-Chloro-2-hydroxy-5-nitropyridine(22353-38-4)1HNMR
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