4-bromo-5-fluoro-2-iodo-phenylamine

4-bromo-5-fluoro-2-iodo-phenylamine Property

Boiling point:

289.2±40.0 °C(Predicted)

Density 

2.354±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.82±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Safety

HS Code 

2921410090

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-bromo-5-fluoro-2-iodo-phenylamine Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 4-bromo-5-fluoro-2-iodoaniline from 4-bromo-3-fluoroaniline was as follows: N-iodosuccinimide (2.90 mL, 28.9 mmol) was slowly added to a solution of 4-bromo-3-fluoroaniline (5.00 g, 26.3 mmol) in acetic acid (52.6 mL). The reaction mixture was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction solution was diluted with toluene (20 mL) and subsequently concentrated under reduced pressure. The concentrated residue was dissolved in ethyl acetate and washed with 2N aqueous sodium hydroxide. The organic phase was further washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (using a 40-g Ultra SNAP column and a 25-g silica gel upconversion column with 2-10% ethyl acetate/heptane as eluent) to afford the target compound 4-bromo-5-fluoro-2-iodoaniline (7.23 g, 22.89 mmol, 87% yield). The product was confirmed by 1H NMR (400 MHz, chloroform-d): δ 7.74-7.78 (m, 1H), 6.53-6.57 (m, 1H). The mass spectrum (ESI) showed a m/z of 315.9 ([M + H]+).

References

[1] Patent: US2012/252853, 2012, A1. Location in patent: Page/Page column 25
[2] Patent: US9212182, 2015, B2. Location in patent: Page/Page column 222
[3] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 98
[4] Patent: US2010/81643, 2010, A1. Location in patent: Page/Page column 125
[5] Patent: WO2012/103806, 2012, A1. Location in patent: Page/Page column 39