2-Chloro-5-iodo-3-nitropyridine Chemical Properties

Melting point:

77-81 °C

Boiling point:

334.0±37.0 °C(Predicted)

Density 

2.213±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-4.74±0.10(Predicted)

form 

solid

Appearance

Off-white to gray Solid

InChI

InChI=1S/C5H2ClIN2O2/c6-5-4(9(10)11)1-3(7)2-8-5/h1-2H

InChIKey

PIJMRJPJERUFNI-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

2933599590

2-Chloro-5-iodo-3-nitropyridine Usage And Synthesis

Uses

2-Chloro-5-iodo-3-nitropyridine is used in preparation of nitrogen heterocycles as colony stimulating factor-1 receptor (CSF-1R) inhibitors.

Synthesis

b) General procedure for the synthesis of 2-chloro-5-iodo-3-nitropyridine from 2-amino-5-iodo-3-nitropyridine: 5-iodo-3-nitropyridin-2-amine (1.3 g, 4.9 mmol) was dissolved in concentrated hydrochloric acid at 0 °C, followed by slow addition of sodium nitrite (6.73 g, 97.13 mmol). Next, a solution of 20 molar equivalents of copper (I) bromide was added dropwise, followed by copper (I) chloride (0.5 g, 4.9 mmol, 1 equiv). The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the mixture was poured into a mixture of ammonium hydroxide and water (1:1, v/v) and extracted with ethyl acetate (3 x 150 mL). The organic phases were combined and washed sequentially with water, aqueous sodium thiosulfate and saturated saline, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to afford the target product 2-chloro-5-iodo-3-nitropyridine in 43% (0.6 g) yield.

References

[1] Patent: WO2013/53983, 2013, A1. Location in patent: Page/Page column 37
[2] Patent: US2015/11548, 2015, A1. Location in patent: Paragraph 0153
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[4] Patent: US6538010, 2003, B1

2-Chloro-5-iodo-3-nitropyridine(426463-05-0)Related Product Information

• 2-CHLORO-5-IODO-3-METHYLPYRIDINE
• 2-Nitrocinnamic acid
• 2-CHLORO-5-IODO-PYRIDIN-3-YLAMINE
• 2-Chloro-5-iodopyridine
• 5-IODO-PYRIDIN-3-YLAMINE
• 2-CHLORO-3-NITROPYRIDINE
• 2-Chloro-5-iodo-3-nitropyridine