3-Iodopyridine Chemical Properties

Melting point:

53-56 °C (lit.)

Boiling point:

90-92°C 14mm

Density 

1.9668 (estimate)

Flash point:

224 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

pK1:3.25(＋1) (25°C)

color 

White to Light yellow to Light red

Sensitive 

Light Sensitive

BRN 

106059

CAS DataBase Reference

1120-90-7(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 3-iodo-(1120-90-7)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-23/24/25

Safety Statements 

26-36-45-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29333990

MSDS

• Language:English Provider:3-Iodopyridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Iodopyridine Usage And Synthesis

Chemical Properties

light beige crystalline powder

Uses

3-Iodopyridine may be used to synthesize following pyridine alkaloids:

• theonelladins C
• theonelladins D
• niphatesine C
• xestamine D

Synthesis

The general procedure for the synthesis of 3-iodopyridine from 3-bromopyridine is as follows: the aromatic Finkelstein reaction is used. Since copper(I) iodide is sensitive to moisture and oxygen, the reaction needs to be carried out under argon protection using the standard Schlenk technique. The procedure is as follows: to a two-necked pear-shaped flask equipped with a reflux condenser is added 3-bromopyridine (as the aryl bromine feedstock), NaI (2 equiv. per bromine exchanged), and CuI (5 mol% per bromine exchanged). N,N'-dimethylethylenediamine (L1) or N,N'-dimethyl-1,2-cyclohexanediamine (L2) (10 mol% used per bromine exchange) and anhydrous 1,4-dioxane (0.5 mL used per 1 mmol NaI) were subsequently added. The resulting suspension was heated to 110°C and maintained for 18 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into a 25% aqueous NH3 solution. The blue solution was diluted to twice the original volume with H2O and extracted three times with CH2Cl2. For the case of 2,2'-bipyridine, the combined organic phases were additionally washed with aqueous EDTA; otherwise, the combined organic phases were simply washed with brine and dried with MgSO4. Subsequently, the solvent is removed by distillation under reduced pressure to give pure 3-iodopyridine. If necessary, the crude product can be further purified by column chromatography or recrystallization.

References

[1] Synthesis (Germany), 2014, vol. 46, # 8, p. 1085 - 1090
[2] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4339 - 4342
[3] Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360
[4] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
[5] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1731 - 1737

3-Iodopyridine(1120-90-7)Related Product Information

• Sulfasalazine
• 2-Chloro-3-iodopyridine
• 3-Aminopyridine
• Pyridine
• 2-Fluoro-3-iodopyridine
• 2-Chloro-3-cyanopyridine
• Chromium picolinate
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 2-Hydroxy-5-iodopyridine
• 2,5-Diiodopyridine
• Bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate
• 3,5-DIIODO-4-PYRIDONE
• 2-Amino-5-iodopyridine
• 4-CHLORO-3-IODOPYRIDINE
• 4-IODOISOQUINOLINE
• (2-CHLORO-PYRIDIN-4-YL)-METHANOL
• 2-Fluoro-5-iodopyridine
• BENZAMIDE, 2-CHLORO-N-(5-IODO-2-PYRIDINYL)-