2-FLUORO-4-IODONICOTINIC ACID Chemical Properties

Boiling point:

347.0±42.0 °C(Predicted)

Density 

2.198

storage temp. 

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

pka

1.20±0.10(Predicted)

form 

solid

color 

Off-white

InChI

InChI=1S/C6H3FINO2/c7-5-4(6(10)11)3(8)1-2-9-5/h1-2H,(H,10,11)

InChIKey

QKPLTGKHTYHYLU-UHFFFAOYSA-N

SMILES

C1(F)=NC=CC(I)=C1C(O)=O

Safety Information

HS Code 

2933399990

2-FLUORO-4-IODONICOTINIC ACID Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-fluoro-4-iodonicotinic acid from 2-fluoro-4-iodopyridine-3-carboxaldehyde was as follows: to a stirred solution of 2-fluoro-4-iodopyridine-3-carboxaldehyde (10.0 g, 39.8 mmol) in a solvent mixture of tert-butanol (350 mL) and water (100 mL) at room temperature was added sequentially 2-methyl-2-butene (42.1 mL, 398 mmol) and sodium chlorite (18.0 g, 199 mmol). 398 mmol), sodium phosphate monohydrate (60.5 g, 438 mmol) and sodium chlorite (18.0 g, 199 mmol). The reaction mixture was stirred continuously for 75 minutes at room temperature. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane and the pH was adjusted to about 2 by slow addition of 6 M aqueous hydrochloric acid. subsequently, the aqueous layer was extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Finally, the target product 2-fluoro-4-iodonicotinic acid (10.63 g, 39.8 mmol, 100% yield) was purified by medium pressure liquid chromatography (MPLC) using a gradient elution (100/0 to 80/20) of dichloromethane/methanol (containing 1% acetic acid). Mass spectrum (ESI positive ion mode) m/z: 268 ([M+H]+). exact mass calculated for C6H3FINO2 was 267.

References

[1] Patent: WO2006/116713, 2006, A1. Location in patent: Page/Page column 194-195
[2] Patent: WO2016/95204, 2016, A1. Location in patent: Page/Page column 62; 63

2-FLUORO-4-IODONICOTINIC ACID(884494-51-3)Related Product Information

• Iodine pentafluoride
• 2-FLUORO-4-IODONICOTINIC ACID METHYL ESTER
• 4-Iodo-3-methylpyridine
• 2-FLUORO-4-IODONICOTINIC ACID
• 2-FLUORO-3-FORMYLPYRIDINE
• 4-IODO-2-FLUORO-3-FORMYLPYRIDINE
• 2-Fluoronicotinic acid
• 2-FLUORO-3-(HYDROXYMETHYL)-4-IODOPYRIDINE
• 4-IODONICOTINIC ACID
• 2-FLUORO-4-IODO-3-PICOLINE
• 2-Fluoro-3-methylpyridine
• 2-FLUORO-3-(HYDROXYMETHYL)PYRIDINE
• 2-Fluoro-3-iodopyridine