4-iodopropiophenone

4-iodopropiophenone Property

Melting point:

54-55 °C

Boiling point:

129-130 °C(Press: 3 Torr)

Density 

1.630±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye 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-iodopropiophenone Chemical Properties,Usage,Production

Synthesis

Iodobenzene (100 g, 0.49 mol) was placed in a dry 1 L three-necked flask fitted with an N2 inlet and 200 mL of carbon disulfide (CS2) was added to it. The reaction mixture was cooled to 0-5 °C, followed by the addition of anhydrous aluminum trichloride (AlCl3, 80 g, 0.6 mol) in batches, followed by the slow dropwise addition of propionyl chloride (60 g, 0.64 mol) while the reaction temperature was controlled to be maintained at 5-10 °C. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the mixture was slowly poured into a 5 L plastic beaker containing 1 L of 10% hydrochloric acid (HCl) and 1 kg of crushed ice. The reaction mixture was extracted with 1 L of ethyl acetate and the organic layer was separated and washed sequentially with 2 x 500 mL of water and 500 mL of saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40 °C to give 4'-iodopropiophenone (48 g, 38% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 7.82 (d, 2H), 7.67 (d, J = 8.30 Hz, 2H), 2.96 (q, J = 7.00 Hz, 2H), 1.22 (t, J = 7.32 Hz, 3H).

References

[1] Patent: WO2010/104488, 2010, A1. Location in patent: Page/Page column 62
[2] Yakugaku Zasshi, 1936, vol. 56, p. 690,696; dtsch. Ref. S. 163, 166
[3] Chem. Zentralbl., 1937, vol. 108, # I, p. 2584
[4] Chemische Berichte, 1941, vol. 74, p. 321,324