2,3-Dichloro-4-iodopyridine Chemical Properties

Melting point:

109-113°C

Boiling point:

284.3±35.0 °C(Predicted)

Density 

2.129±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-0.80±0.10(Predicted)

color 

Cream

InChIKey

WRPBPDPXVUBWCR-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2933399990

2,3-Dichloro-4-iodopyridine Usage And Synthesis

Synthesis

Step 1: Synthesis of 2,3-dichloro-4-iodopyridine Under argon protection, 2,3-dichloropyridine (20 g, 135.1 mmol) was dissolved in anhydrous tetrahydrofuran (350 mL), and cooled to -78 °C. At -78 °C, n-butyllithium (2.4 M hexane solution, 59.12 mL, 141.9 mmol) was slowly added dropwise, and after completion of the dropwise addition, the reaction mixture was continued to be stirred at -78 °C for 90 min. Subsequently, anhydrous tetrahydrofuran (100 mL) solution of iodine (41 g, 161.5 mmol) was slowly added dropwise, and after completion of the dropwise addition, stirring was continued at -78°C for 60 minutes. After completion of the reaction, the reaction mixture was slowly warmed up to room temperature. The reaction was quenched with saturated ammonium chloride solution (100 mL), diluted with water (100 mL) and extracted with ethyl acetate (200 mL x 3). The organic phases were combined, washed with brine solution (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether: ethyl acetate= 100:1) to afford the yellow solid product 2,3-dichloro-4-iodopyridine (31.5 g, yield: 85.1%). 1H NMR (300 MHz, DMSO-d6): δ 8.08 (d, J = 5.4 Hz, 1H), 8.65 (d, J = 5.4 Hz, 1H). MS (ESI+): m/z 273.9 [M + H]+.

References

[1] Patent: US2017/29404, 2017, A1. Location in patent: Paragraph 0122-0125
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2688 - 2701
[3] Patent: WO2006/59778, 2006, A1. Location in patent: Page/Page column 57-58
[4] Patent: EP1820797, 2007, A1
[5] Patent: WO2013/5057, 2013, A1. Location in patent: Page/Page column 118

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