2-Chloro-3-fluoro-4-iodopyridine Chemical Properties

Melting point:

97 °C

Boiling point:

246.1±35.0 °C(Predicted)

Density 

2.129±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-0.22±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C5H2ClFIN/c6-5-4(7)3(8)1-2-9-5/h1-2H

InChIKey

GONULLRFSHKLBS-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(I)=C1F

CAS DataBase Reference

148639-07-0(CAS DataBase Reference)

Safety Information

HS Code 

2933399990

2-Chloro-3-fluoro-4-iodopyridine Usage And Synthesis

Uses

2-Chloro-3-fluoro-4-iodopyridine is a polyhalogenated compound with a wide uses. It is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

The general procedure for the synthesis of 2-chloro-3-fluoro-4-iodopyridine using 2-chloro-3-fluoropyridine as a starting material was as follows: a lithium 2-diisopropylammonium solution (2M, dissolved in a mixed solvent of tetrahydrofuran/ethylbenzene/heptane, 155 mL, 0.31 mol) was added slowly and dropwise over a period of 40 min at -70 °C to a 2-chloro-3-fluoropyridine (31 g, 0.235 mol) tetrahydrofuran (200 mL) solution. After the dropwise addition, the reaction mixture was continued to be stirred at -70 °C for 4 hours. Subsequently, a solution of iodine (69 g, 0.2 mol) in tetrahydrofuran (100 mL) was added dropwise over a period of 30 min, and after keeping the reaction at -70 °C for 30 min, the reaction was slowly warmed up to room temperature, and the warming up process was controlled to be completed in 1 hour. The reaction mixture was poured into aqueous sodium bisulfite solution (20% v/v, 2 L) and extracted with ether (3 x 300 mL). The organic phases were combined and washed sequentially with aqueous sodium metabisulfite (20% v/v, 2L) and water (200 mL), dried with anhydrous sodium sulfate and concentrated under reduced pressure to give a colorless oily substance. The oily material was ground with ether to afford the target product 2-chloro-3-fluoro-4-iodopyridine as a reddish brown solid (28 g, 46% yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 7.87 (d, J=5.0 Hz, 1H), 7.66 (ddd, J=5.0,4.0,0.4 Hz, 1H).

References

[1] Patent: WO2012/35039, 2012, A1. Location in patent: Page/Page column 107-108
[2] Tetrahedron, 1993, vol. 49, # 16, p. 3325 - 3342

2-Chloro-3-fluoro-4-iodopyridine(148639-07-0)Related Product Information

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• 2-Chloro-3-iodopyridine
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• 3-BROMO-5-FLUORO-2-METHOXYPYRIDINE
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• 3-AMINO-2-CHLORO-5-PICOLINE
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• 4-Bromo-2-chloro-3-iodopyridine
• 3-Amino-2-chloro-4-methylpyridine
• 5-Amino-2-chloro-3-picoline
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• 2-Chloro-3-methyl-5-nitropyridine
• 2-Chloro-3-methyl-5-bromopyridine
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