2-Hydroxy-5-iodo-3-nitropyridine

2-Hydroxy-5-iodo-3-nitropyridine Property

Melting point:

252-256°C

Boiling point:

314.0±42.0 °C(Predicted)

Density 

2.27±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

6.50±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Hydroxy-5-iodo-3-nitropyridine Chemical Properties,Usage,Production

Synthesis

3-Nitropyridin-2(1H)-one (10.3 g, 73.4 mmol, 1 eq.) was used as a raw material and suspended in a mixed solution of 46 mL acetic acid, 20 mL water, 1.4 mL concentrated sulfuric acid and periodate (3.5 g, 18 mmol, 0.25 eq.). The reaction mixture was stirred at 90 °C for 15 min until completely dissolved. Subsequently, iodine crystals (7.7 g, 30.1 mmol, 0.4 eq.) were added in batches and formation of a dense yellow precipitate was observed after 20 min of reaction. The reaction mixture was cooled to room temperature and 50 mL of saturated sodium thiosulfate solution was added to quench the reaction. The solid product was collected by filtration and washed sequentially with 50 mL of saturated sodium thiosulfate solution and water. Finally, the solid was dried under vacuum to give 5-iodo-3-nitropyridin-2-ol (XIII-2, 14 g, 72% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 12, p. 3973 - 3977
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5785 - 5788
[3] Patent: US2014/94456, 2014, A1. Location in patent: Paragraph 0656-0657
[4] Patent: WO2015/153683, 2015, A1. Location in patent: Paragraph 0413
[5] Bioorganic & Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 525 - 528