2-chloro-5-(trifluoromethyl)-4-iodopyridine Chemical Properties

Melting point:

126.0 to 130.0 °C

Boiling point:

257.6±40.0 °C(Predicted)

Density 

2.046±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Solid

pka

-2.74±0.10(Predicted)

color 

Light Tan

Sensitive 

Light Sensitive

InChI

InChI=1S/C6H2ClF3IN/c7-5-1-4(11)3(2-12-5)6(8,9)10/h1-2H

InChIKey

XEEQBBXEZSNIQV-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(C(F)(F)F)C(I)=C1

CAS DataBase Reference

505084-55-9

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2-chloro-5-(trifluoromethyl)-4-iodopyridine Usage And Synthesis

Uses

2-Chloro-4-iodo-5-(trifluoromethyl)pyridine is used in preparation of pyridine-2,4-diamine derivatives as FAK inhibitors for the treatment of arthritis, inflammatory and immune disorders.

Uses

2-chloro-5-(trifluoromethyl)-4-iodopyridine is used in preparation of pyridine-2,4-diamine derivatives as FAK inhibitors for the treatment of arthritis, inflammatory and immune disorders.

Synthesis

The general procedure for the synthesis of 2-chloro-5-trifluoromethyl-4-iodopyridine from 2-chloro-5-trifluoromethylpyridine was as follows: diisopropylamine (3.3330 g, 32.94 mmol) and anhydrous THF (33 mL) were added to 100 mL of a cigar shaped flask and protected under Ar atmosphere. The reaction system was cooled to -78 °C, n-butyllithium (1.58 M hexane solution, 20.8 mL, 32.86 mmol) was slowly added dropwise and stirred at the same temperature for 10 min. Subsequently, 2-chloro-5-trifluoromethylpyridine (5.4616 g, 30.08 mmol) dissolved in anhydrous THF (30 mL) was added slowly dropwise at -78 °C and stirring was continued at the same temperature for 1 hour. Next, iodine (9.2188 g, 36.32 mmol) dissolved in anhydrous THF (30 mL) was added dropwise at -78 °C and stirred at the same temperature for 30 min before slowly warming to 0 °C. The reaction was quenched by the addition of 1 M aqueous sodium thiosulfate (50 mL) at 0 °C. The reaction was extracted three times with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. After removal of the solvent by distillation under reduced pressure, the resulting residue was purified by silica gel column chromatography (BW-200,80 g, eluent 30% benzene/hexane) to afford the target product 2-chloro-5-trifluoromethyl-4-iodopyridine (4.3977 g, 14.30 mmol, 48% yield). In addition, a white powdery product was obtained by recrystallization from EtOH.

References

[1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[2] Patent: JP2016/700, 2016, A. Location in patent: Paragraph 0032
[3] Patent: WO2008/115369, 2008, A2. Location in patent: Page/Page column 50-51

2-chloro-5-(trifluoromethyl)-4-iodopyridine(505084-55-9)Related Product Information

• Forchlorfenuron
• 6-CHLORO-3-(TRIFLUOROMETHYL)-2-IODOPYRIDINE
• 2-Chloro-4-iodopyridine
• 2-Chloro-5-trifluoromethylpyridine
• 2-chloro-5-(trifluoromethyl)-4-iodopyridine
• 4-Iodo-3-methylpyridine
• 4-Iodopyridine