3-Iodopyridin-2-amine Chemical Properties

Melting point:

87-91 °C

Boiling point:

289.6±25.0 °C(Predicted)

Density 

2.055±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

pka

4.50±0.36(Predicted)

form 

Powder, Crystalline Powder or Needles

color 

White to pale brown

Sensitive 

Air & Light Sensitive

InChI

InChI=1S/C5H5IN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)

InChIKey

UUDNBWSHTUFGDQ-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC=C1I

CAS DataBase Reference

104830-06-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

3-Iodopyridin-2-amine Usage And Synthesis

Chemical Properties

Light yellow Needles

Uses

2-Amino-3-iodopyridine (3-Iodopyridin-2-amine) can be coupled with formyl derivatives under a copper-catalyzed indole synthesis method, and then constructed azide analogs through copper-mediated conjugated adducts things. The nucleophilicity of 2-Amino-3-iodopyridine is lower than that of the corresponding aniline used in the synthesis of indole, a potential obstacle for future synthesis[1].

Synthesis

General procedure for the synthesis of 2-amino-3-iodopyridine from N-(3-iodopyridin-2-yl)palmitamide: N-(3-iodopyridin-2-yl)neopentanamide (13.80 g, 45.36 mmol) was dissolved in 24 wt% sulfuric acid solution (394 mL), and the reaction mixture was stirred for 60 min under reflux conditions. After completion of the reaction, it was cooled to room temperature and neutralized with 4N sodium hydroxide solution and solid sodium bicarbonate. The aqueous phase was extracted with dichloromethane (3 x 200 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporator to give 3-iodopyridin-2-amine (9.70 g, 97% yield) as a cream colored solid.

References

[1] Patent: US2009/156593, 2009, A1. Location in patent: Page/Page column 17
[2] Patent: US2006/183758, 2006, A1. Location in patent: Page/Page column 8
[3] Patent: US2009/82403, 2009, A1. Location in patent: Page/Page column 51
[4] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 53
[5] Patent: US2010/331282, 2010, A1. Location in patent: Page/Page column 10

3-Iodopyridin-2-amine(104830-06-0)Related Product Information

• Triethylamine
• 2-Chloro-3-hydroxypyridine
• N-Ethylmethylamine
• 4-Dimethylaminopyridine
• Triethanolamine
• Dibenzylamine
• 3-Hydroxypyridine
• 2-Aminopyridine
• 3-Aminopyridine
• Bis(2-ethylhexyl)amine
• 2-AMINO-3,5-DIIODOPYRIDINE
• 3-IODO-2-NITROPYRIDINE
• 1-(3-IODO-PYRIDIN-2-YL)-PIPERAZINE
• 5-Bromo-3-iodopyridin-2-amine
• N-CYCLOPROPYL-3-IODOPYRIDIN-2-AMINE
• 2-AMINO-3-IODO-5-NITROPYRIDINE
• 2-Amino-3-iodo-6-methylpyridine
• 4-(3-IODO-PYRIDIN-2-YL)-MORPHOLINE