2-Iodo-6-methylpyridine Chemical Properties

Boiling point:

222.1±20.0 °C(Predicted)

Density 

1.810±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.57±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

HS Code 

2933399990

2-Iodo-6-methylpyridine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-iodo-6-methylpyridine from 2-bromo-6-methylpyridine and acetyl chloride: to an anhydrous acetonitrile (13 mL) solution of 2-bromo-6-methylpyridine (2.0 g, 11.6 mmol) and sodium iodide (2.78 g, 18.6 mmol) was slowly added acetyl chloride (1.9 g, 24.4 mmol) dropwise, and the reaction mixture formed a light-yellow The reaction mixture formed a pale yellow suspension. The suspension was heated to reflux. After 16 hours of reaction, the conversion was shown to be 50% by gas chromatography (GC) analysis. Subsequently, acetyl chloride (1 eq.) and sodium iodide (0.8 eq.) were added additionally and refluxing was continued for 16 h. GC analysis showed 90% conversion with the presence of bromine and chlorine by-products detected. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with 10% aqueous potassium carbonate and 5% aqueous sodium bisulfite (75 mL each), and extracted with ether (2 x 75 mL). The organic phases were combined, washed with potassium carbonate/sodium bisulfite solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 2.39 g (94%) of the crude product 2-iodo-6-methylpyridine as a dark oil, which was directly used in the subsequent reaction without further purification. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.52 (s, 3H), 7.10 (d, 1H, J = 7.51 Hz), 7.20 (t, 1H, J = 7.69 Hz), 7.58 (d, 1H, J = 7.69 Hz). Ref: Tetrahedron Lett. 1990, 31, 6757.

References

[1] Patent: US2002/19370, 2002, A1

2-Iodo-6-methylpyridine(62674-71-9)Related Product Information

• 3-Hydroxy-2-iodo-6-methylpyridine
• 6-IODO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• 2-Iodo-6-methylpyridine
• 3,6-DIIODOPYRIDINE-2-CARBONITRILE
• 2-Methyl-3-hydroxy-6-iodopyridine
• (6-IODO-PYRIDIN-2-YL)-METHANOL
• 6-IODO-PYRIDINE-2-CARBOXYLIC ACID
• 2,4-Diiodo-3-hydroxy-6-methylpyridine
• 2-Iodo-6-(trifluoromethyl)pyridine
• 6-IODO-PYRIDINE-2-CARBOXYLIC ACID HYDRAZIDE
• 2-iodo-6-methyl-3-pyridinyl methyl ether
• 6-IODO-PYRIDINE-2-CARBOXYLIC ACID AMIDE
• 3-Amino-2-iodo-6-(trifluoromethyl)-pyridine
• 6-IODO-2,2'-BIPYRIDINE N-OXIDE
• 6-IODO-5-METHOXY-2-PYRIDINECARBOXYLIC ACID
• 6-IODO-4-METHOXY-2,2'-BIPYRIDINE
• 6,6'-DIIODO-2,2'-BIPYRIDINE