4-IODO-2-FLUORO-3-FORMYLPYRIDINE Chemical Properties

Boiling point:

304.2±42.0 °C(Predicted)

Density 

2.081±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

-3.62±0.18(Predicted)

color 

Yellow

InChI

InChI=1S/C6H3FINO/c7-6-4(3-10)5(8)1-2-9-6/h1-3H

InChIKey

VONGIOGTLFSXDE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

153034-82-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant

HS Code 

2933399990

4-IODO-2-FLUORO-3-FORMYLPYRIDINE Usage And Synthesis

Application

2-Fluoro-3-aldehyde-4-iodopyridine is a heterocyclic organic compound that can be used as a pharmaceutical synthesis intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 7832, 1993 DOI: 10.1021/jo00079a031

Synthesis

To a solution of diisopropylamine (174.4 g, 1.73 mol) in anhydrous THF (3 L) was added slowly and dropwise 2.5 M hexane solution of n-butyllithium (n-BuLi) (685 mL, 1.71 mol) at -10 °C. The reaction mixture was stirred at 0 °C for 35 min. Subsequently, the mixture was cooled to -70 °C and a solution of anhydrous THF (1 L) of 2-fluoro-3-iodopyridine (350 g, 1.57 mol) was added. The mixture was continued to be stirred at -70 °C for 2 hours. Ethyl formate (HCOOEt) (128 g, 1.73 mol) was slowly added dropwise while maintaining -70 °C. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and the reaction was quenched with ice water (4 L). The reaction mixture was diluted with ethyl acetate (EtOAc) (4 L) and the organic layer was washed with brine (500 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent being petroleum ether: ethyl acetate (10:1, v/v) to afford the target product 2-fluoro-4-iodopyridine-3-carbaldehyde (180 g, 46% yield) as a yellow solid.1H NMR (400 MHz, CDCl3) δ ppm: 10.08 (s, 1H), 7.91 (d, 1H), 7.81 (d, 1H). 1H).

References

[1] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[2] Patent: WO2016/97918, 2016, A1. Location in patent: Page/Page column 58

4-IODO-2-FLUORO-3-FORMYLPYRIDINE(153034-82-3)Related Product Information

• 2-Fluoro-4-iodopyridine
• 2-Fluoro-3-iodopyridine
• 2-Fluoro-3-methylpyridine
• 4-IODO-2-FLUORO-3-FORMYLPYRIDINE
• 2-FLUORO-4-IODO-3-PICOLINE
• 4-Iodopyridine
• 4-Iodo-3-methylpyridine
• 2-FLUORO-4-IODONICOTINIC ACID METHYL ESTER
• 2-FLUORO-4-IODONICOTINIC ACID
• 2-FLUORO-3-FORMYLPYRIDINE