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

pka

6.89±0.10(Predicted)

color 

Yellow

Water Solubility 

Insoluble in water.

BRN 

149557

InChI

InChI=1S/C5H3ClN2O3/c6-3-1-2-7-5(9)4(3)8(10)11/h1-2H,(H,7,9)

InChIKey

UKIZCTHOMJXNIX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

165547-79-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

4-Chloro-2-hydroxy-3-nitropyridine Usage And Synthesis

Uses

4-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

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(165547-79-5)Related Product Information

• Zinc pyrithione
• 4-Nitroacetophenone
• 2-Hydroxypyridine
• 3-Nitroacetophenone
• 4-Chloro-3-nitropyridine
• 4-Hydroxy-3-nitropyridine
• 1-Chloro-3-nitrobenzene
• Clopidol
• 3-Nitro-2-pyridinol
• 2-Chloro-5-chloromethylpyridine
• CHLOROPHOSPHONAZO III
• 4-Chloronitrobenzene
• NITROGEN DIOXIDE
• Difluorochloromethane
• 3-Chloro-2-hydroxy-5-nitropyridine ,97%,3-CHLORO-2-HYDROXY-5-NITROPYRIDINE
• 5-CHLORO-2-HYDROXY-3-NITROPYRIDINE,5-Chloro-2-hydroxy-3-nitropyridine 95+%,5-Chloro-2-hydroxy-3-nitropyridine ,97%
• 4-CHLORO-6-METHYL-3-NITROPYRIDIN-2(1H)-ONE
• 4-Chloro-2-hydroxy-5-nitropyridine