2-AMINO-5-IODO-3-NITROPYRIDINE Chemical Properties

Melting point:

215-219 °C (lit.)

Boiling point:

365.4±42.0 °C(Predicted)

Density 

2.229±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

0.41±0.49(Predicted)

Appearance

Light yellow to yellow Solid

CAS DataBase Reference

25391-57-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich

2-AMINO-5-IODO-3-NITROPYRIDINE Usage And Synthesis

Uses

2-Amino-5-iodo-3-nitropyridine is used in the synthetic preparation of disubstituted pyridinyl azabicyclo heptanes as epibatidine analogs. These analogs are evaluated for its affinity for nicotinic acetylcholine receptors via in vitro and antinociceptive properties via in vivo in rats.

Synthesis

To a 250 mL three-necked flask were added 2-amino-3-nitropyridine (10.0 g, 72.0 mmol), acetic acid (44 mL) and water (10 mL). The mixture was heated to 90°C and then periodic acid (3.28 g, 14.4 mmol) and concentrated sulfuric acid (1.3 mL) at a mass percent concentration of 98% were added sequentially. After stirring for 10 min, iodine (9.1 g, 36.0 mmol) was added and stirring was continued for 60 min at this temperature. Upon completion of the reaction, the reaction solution was cooled to room temperature and subsequently poured into saturated aqueous sodium thiosulfate solution (100 mL). The solid product was separated by filtration and washed sequentially with saturated brine (50 mL x 2) and petroleum ether (50 mL x 2). The crude product was recrystallized using a mixed solvent of petroleum ether and ethyl acetate (5:1, v/v) to afford a high purity yellow solid 2-amino-5-iodo-3-nitropyridine (17.57 g, 69.1 mmol, 96% yield).

References

[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[2] Patent: CN107325045, 2017, A. Location in patent: Paragraph 0006; 0009
[3] Patent: WO2013/53983, 2013, A1. Location in patent: Page/Page column 37
[4] Patent: US2015/11548, 2015, A1. Location in patent: Paragraph 0152

2-AMINO-5-IODO-3-NITROPYRIDINE(25391-57-5)Related Product Information

• 2-AMINO-3-IODO-5-NITROPYRIDINE
• 5-IODO-PYRIDIN-3-YLAMINE
• 2-amino-5-iodo-3-pyridinylamine
• 2-AMINO-5-IODO-3-NITROPYRIDINE