4-Iodopyridine Chemical Properties

Melting point:

94-99 °C

Boiling point:

212~215℃

Density 

1.081g/cm3

refractive index 

1.5290

storage temp. 

-20°C

solubility 

soluble in Methanol

form 

Crystals or Powder

pka

pK1:4.02(＋1) (20°C)

color 

Pale brown to dark green-brown

Sensitive 

Light Sensitive

BRN 

1594

InChI

InChI=1S/C5H4IN/c6-5-1-3-7-4-2-5/h1-4H

InChIKey

RTLUPHDWSUGAOS-UHFFFAOYSA-N

SMILES

C1=NC=CC(I)=C1

CAS DataBase Reference

15854-87-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

26-36-39

WGK Germany 

3

Hazard Note 

Irritant/Light Sensitive

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

4-Iodopyridine Usage And Synthesis

Chemical Properties

White to off-white crystals,turns brown on storage

Uses

4-Iodopyridine is used as a reagent in the synthesis of indazolylamides as glucocorticoid receptor agonists.

Synthesis

GENERAL METHODS: [Li(TMP)Zn(tBu)2] 1 was prepared according to literature methods in a 0.4 mmol scale solution of THF. Pyridine (0.032 mL, 0.4 mmol) was added to this solution at 0°C and the resulting light orange colored reaction mixture was allowed to stir for 2 h at room temperature. Subsequently, the reaction was quenched with I2 (508 mg, dissolved in 1 mL THF) and stirring was continued for 1 hour. A 10% Na2S2O3 solution was added until the color of the reaction mixture faded, and then the product was extracted with DCM (3 x 1 mL). The organic extracts were combined, dried with MgSO4 and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using EtOAc:heptane (20:80→30:70) as eluent to afford 4-iodopyridine (compound 5a) as an off-white solid (42 mg, 50% yield).1H NMR (400 MHz, CDCl3) δ ppm 7.59-7.86 (m, 2H), 8.07-8.44 (m 2H).

References

[1] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[2] Journal of Organic Chemistry, 1984, vol. 49, # 20, p. 3857 - 3859

4-Iodopyridine(15854-87-2)Related Product Information

• Clopyralid
• Chromium picolinate
• Sulfasalazine
• Pyridine
• 4-Methylpyridine
• 2-Bromo-5-iodopyridine
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 2-Fluoro-4-iodopyridine
• 2-CHLORO-4-IODOPYRIDINE,99%
• 2-Chloro-4-iodopyridine-3-carboxaldehyde
• 2-Fluoro-3-iodopyridine
• 2-Bromo-4-iodopyridine
• 2-CHLORO-4-IODO-3-METHYLPYRIDINE
• 3-CHLORO-4-IODOPYRIDINE
• 2-FLUORO-3-FORMYL-4-IODOPYRIDINE
• 2,6-Dichloro-3-iodopyridine
• 2-ETHOXY-3-IODO-PYRIDINE
• 3,5-DICHLORO-4-IODOPYRIDINE, 97%