5-CHLORO-2-IODOPHENOL Chemical Properties

Boiling point:

219℃

Density 

2.087

Flash point:

86℃

storage temp. 

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

pka

7.55±0.10(Predicted)

form 

tiny crystals

color 

Golden brown & dark tan

Safety Information

HS Code 

2908190090

5-CHLORO-2-IODOPHENOL Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-chloro-2-iodophenol from 2-amino-5-chlorophenol: 2-amino-5-chlorophenol (5.7 g, 40 mmol) was dissolved in a mixed solvent of DMSO/water/H2SO4 (200/60/140 mL) and the solution was cooled to 0 °C. A solution of sodium nitrite (4.1 g, 60 mmol) in water (20 mL) was slowly added at 0 °C and the reaction mixture was continuously stirred for 1 hour. Subsequently, a solution of potassium iodide (19.9 g, 120 mmol) in water (20 mL) was added to the reaction system and the mixture was stirred at room temperature for 1 hour. The same amount of potassium iodide (19.9 g, 120 mmol) in water (20 mL) solution was added again and the mixture continued to be stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed sequentially with water, saturated aqueous sodium sulfate solution and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by fast chromatography (Biotage? Si65M, 20% ethyl acetate/hexane) to afford 5-chloro-2-iodophenol 8.09 g (79% yield) as a pink solid. gC-MS m/e 254 [M]-.

References

[1] Patent: US2010/69425, 2010, A1. Location in patent: Page/Page column 11-12
[2] Journal of the Chemical Society, 1931, p. 2268,2271

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