2-Chloro-4-iodopyridine Chemical Properties

Melting point:

42-43 °C (lit.)

Boiling point:

255.5±20.0 °C(Predicted)

Density 

2.052±0.06 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate

form 

Crystals or Crystalline Flakes

pka

-0.03±0.10(Predicted)

color 

White to yellow

Sensitive 

Light Sensitive

BRN 

108668

CAS DataBase Reference

153034-86-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-41-43-36/37/38-20/22

Safety Statements 

26-36/37/39-36-22

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant/Light Sensitive

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-4-iodopyridine Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

2-Chloro-4-iodopyridine (cas# 153034-86-7) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 2-chloro-4-iodopyridine from 2-chloro-3-iodopyridine: 2-chloro-3-iodopyridine (12 g, 50 mmol) was prepared as a solution by dissolving it in 20 mL of tetrahydrofuran (THF). The solution was slowly added to a pre-prepared lithium diisopropylammonium solution at -78°C (the lithium diisopropylammonium solution was prepared by reacting 1.6 M n-butyllithium hexane solution (31.25 mL, 50 mmol) with diisopropylamine (7 mL, 50 mmol) in 100 mL THF). After 3 hours of reaction, the reaction was quenched by adding 20 mL of water to the reaction mixture, followed by extraction with ether (2 x 100 mL). The organic layers were combined, dried with magnesium sulfate, filtered and concentrated under vacuum at 20 °C to give a brown solid. Purification by silica gel column chromatography (eluent: ethyl acetate/heptane=8/2) gave light yellow needle-like crystals in 95% yield (11.4 g). The structure of the product was analyzed by 1H NMR (CDCl3): δ 8.07 (d, J = 5.3 Hz, 1H), 7.76 (d, J = 1.1 Hz, 1H), 7.59 (dd, J = 5.0/0.11 Hz, 1H); 13C NMR (CDCl3): δ 151.7, 149.6, 133.0, 131.5, 106.6; MS ( EI) m/z 240 (M + 1) confirmed.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1397 - 1401
[2] Patent: WO2004/52880, 2004, A1. Location in patent: Page 30
[3] Patent: US2009/186899, 2009, A1. Location in patent: Page/Page column 45-46
[4] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[5] Patent: US2008/249128, 2008, A1. Location in patent: Page/Page column 46

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