2-Chloro-3-iodo-5-nitropyridine

2-Chloro-3-iodo-5-nitropyridine Property

Melting point:

102-106°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

Appearance

Off-white to gray Solid

Safety

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

Synthesis

General procedure for the synthesis of 2-chloro-3-iodo-5-nitropyridine from 3-iodo-2-hydroxy-5-nitropyridine: 1. a mixture of 3-iodo-5-nitropyridin-2-ol (37.60 mmol, 10 g), phosphorus trichloride (POCl3, 86.47 mmol, 7.94 mL), and phosphorus pentachloride (PCl5, 48.87 mmol, 10.2 g) was heated under argon protection for 45 min at 140 °C. 2. After completion of the reaction, the mixture was cooled to room temperature, slowly poured into ice water and extracted with dichloromethane (DCM). 3. The organic phase was washed sequentially with water, aqueous sodium bicarbonate (NaHCO3) and brine. 4. The solvent was removed by evaporation and the crude product was purified by column chromatography on silica gel (SiO2), eluting with a hexane/dichloromethane solvent mixture to afford the target product, 2-chloro-3-iodo-5-nitropyridine (7.32 g, 69% yield). 5. The structure of the product was determined by 1H NPD analysis. 5. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 8.90 (s, 1H), 9.19 (s, 1H). Note: Repeat steps have been combined to ensure conciseness and accuracy of experimental steps.

References

[1] Australian Journal of Chemistry, 2008, vol. 61, # 6, p. 438 - 445
[2] Patent: EP2599771, 2013, A1. Location in patent: Paragraph 0505
[3] Patent: WO2015/73528, 2015, A1. Location in patent: Page/Page column 191
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 13, p. 2841 - 2849
[5] Patent: WO2009/21696, 2009, A1. Location in patent: Page/Page column 37-38; 41; 69