4-chloro-5-fluoro-2-iodoaniline

4-chloro-5-fluoro-2-iodoaniline Property

Boiling point:

293.8±40.0 °C(Predicted)

Density 

2.089±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.88±0.10(Predicted)

Appearance

Light brown to gray Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-chloro-5-fluoro-2-iodoaniline Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 4-chloro-5-fluoro-2-iodoaniline from 3-fluoro-4-chloroaniline was as follows: iodide iodide (20.6 mL, 1 M dichloromethane solution, 20.6 mmol) was added slowly and dropwise to a solution of 4-chloro-3-fluoroaniline (2 g, 13.7 mmol) in methanol (35 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, volatiles were removed by distillation under reduced pressure, water was added and the mixture was extracted with dichloromethane. The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and then the solvent was evaporated. The remaining crude product was purified by silica gel column chromatography using three different ratios of eluents in sequence (heptane/ethyl acetate 98:2-93:7, and twice heptane/ethyl acetate 98:2-95:5), resulting in 4-chloro-5-fluoro-2-iodoaniline (2.51 g, 67% yield) as a dark red solid. Mass spectrometry (ESI) analysis showed a molecular ion peak of 272.1 (M + H)+.

References

[1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1248 - 1253
[2] Patent: WO2013/64465, 2013, A1. Location in patent: Page/Page column 168
[3] Patent: US2013/116234, 2013, A1. Location in patent: Paragraph 0940; 0941
[4] Patent: US2009/5410, 2009, A1. Location in patent: Page/Page column 78
[5] Patent: WO2013/56060, 2013, A1. Location in patent: Paragraph 00237