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4-Chloro-2-hydroxy-3-nitropyridine

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4-Chloro-2-hydroxy-3-nitropyridine Basic information
Product Name:4-Chloro-2-hydroxy-3-nitropyridine
Synonyms:4-Chloro-2-hydroxy-3-nitropyridine;4-Chloro-3-nitro-2-hydroxypyridine;2--3--4-;4-CHLORO-3-NITRO-2-PYRIDONE;4-CHLORO-3-NITROPYRIDONE;2-HYDROXY-3-NITRO-4-CHLOROPYRIDINE;2(1H)-Pyridinone, 4-chloro-3-nitro-;4-Chloro-3-nitro-1H-pyridin-2-one
CAS:165547-79-5
MF:C5H3ClN2O3
MW:174.54
EINECS:000-000-0
Product Categories:Pyridine;Heterocycle-Pyridine series
Mol File:165547-79-5.mol
4-Chloro-2-hydroxy-3-nitropyridine Structure
4-Chloro-2-hydroxy-3-nitropyridine Chemical Properties
Melting point 222-224°C
Boiling point 283.4±40.0 °C(Predicted)
density 1.61±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Store in freezer, under -20°C
form solid
pka6.89±0.10(Predicted)
color Yellow
Water Solubility Insoluble in water.
BRN 149557
InChIInChI=1S/C5H3ClN2O3/c6-3-1-2-7-5(9)4(3)8(10)11/h1-2H,(H,7,9)
InChIKeyUKIZCTHOMJXNIX-UHFFFAOYSA-N
SMILESC1(=O)NC=CC(Cl)=C1[N+]([O-])=O
CAS DataBase Reference165547-79-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
HS Code 2933399990
MSDS Information
ProviderLanguage
ALFA English
4-Chloro-2-hydroxy-3-nitropyridine Usage And Synthesis
Uses4-Chloro-3-nitro-2-pyridone finds an important application as raw material in organic synthesis and pharmaceuticals. It is also used as an intermediate in agrochemicals and dyestuffs.
Synthesis
2,4-Dihydroxy-3-nitropyridine

89282-12-2

4-Chloro-2-hydroxy-3-nitropyridine

165547-79-5

General procedure for the synthesis of 2-hydroxy-3-nitro-4-chloropyridine from 4-hydroxy-3-nitropyridin-2(1H)-one: to 2,4-dihydroxy-3-nitropyridine (5.00 g, 0.032 mol), dimethyl chloride (4.07 g, 0.032 mol), and 5 drops of DMF were added to 2,4-dihydroxy-3-nitropyridine (5.00 g, 0.032 mol) and slowly added dropwise to dichloromethane (80 mL) at 0°C. . The reaction mixture was stirred at room temperature for 4 hours. After the reaction was complete, it was diluted by adding dichloromethane (100 mL). The organic layer was washed sequentially with saturated sodium bicarbonate solution, water and saturated saline. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-hydroxy-3-nitro-4-chloropyridine (5.00 g, 89% yield).

References[1] Organic Process Research and Development, 2013, vol. 17, # 12, p. 1561 - 1567
[2] Patent: CN108498516, 2018, A. Location in patent: Paragraph 0023; 0025; 0026; 0027; 0028
[3] Patent: WO2017/14323, 2017, A1. Location in patent: Paragraph 0250
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4986 - 4989
[5] Patent: US2012/289497, 2012, A1. Location in patent: Page/Page column 29
4-Chloro-2-hydroxy-3-nitropyridine Preparation Products And Raw materials
Raw materials2,4-Dihydroxy-3-nitropyridine-->2,4-Dichloro-3-nitropyridine-->N,N-Dimethylformamide-->Dichloromethane-->Oxalyl chloride
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