4-Fluoro-2-iodophenol

4-Fluoro-2-iodophenol Property

Melting point:

120-123℃

Boiling point:

196℃

Density 

2.085

Flash point:

73℃

storage temp. 

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

form 

crystalline solid

pka

8.53±0.18(Predicted)

color 

Orange to brown

Safety

HS Code 

2907290090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P309+P311IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.

4-Fluoro-2-iodophenol Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-fluoro-2-iodophenol from 4-fluorophenol: Methanol (200 mL), 4-fluorophenol (8.00 g, 71.37 mmol), sodium iodide (12.84 g, 85.64 mmol), and sodium hydroxide (3.43 g, 85.64 mmol) were added to a round-bottomed flask fitted with a dosing funnel under nitrogen protection, maintaining the reaction temperature at 0-10°C. After stirring for 15 min, sodium hypochlorite solution (133 mL, 5% v/v, commercially available bleach, 92.77 mmol) was slowly added dropwise. After the dropwise addition was completed, stirring was continued at 0-10 °C for 1 hour. Subsequently, 100 mL of 10 wt% aqueous sodium thiosulfate was added to the reaction mixture. After acidifying the reaction mixture with 5% hydrochloric acid, it was extracted with dichloromethane (500 mL). The organic phase was washed sequentially with 500 mL of 10 wt% aqueous sodium thiosulfate solution, water and saturated saline, and then dried with anhydrous magnesium sulfate. The dried organic phase was filtered through a silica gel pad and concentrated to give an oily crude product. The crude product was purified by recrystallization from hexane to give 11.52 g of pure product in white crystal form in 67.8% yield. The structure of the product was confirmed by 1H NMR, 13C NMR and mass spectrometry: 1H NMR (500 MHz, chloroform-d) δ 7.36 (dd, J = 7.6, 2.9 Hz, 1H), 6.97 (ddd, J = 8.9, 7.7, 2.9 Hz, 2H), 6.92 (dd, J = 9.0, 4.9 Hz, 1H), 5.10 (s, 1H) ; 13C NMR (101 MHz, chloroform-d) δ 156.42 (d, J = 243.0 Hz), 151.45 (d, J = 2.6 Hz), 124.34 (d, J = 25.3 Hz), 116.83 (d, J = 23.1 Hz), 115.08 (d, J = 7.8 Hz), 84.23 (d, J = 9.0 Hz ); MS m/e 238.

References

[1] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 1, p. 3 - 6
[2] Chemical Communications, 2016, vol. 52, # 29, p. 5152 - 5155
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1956 - 1960
[4] Patent: WO2016/89935, 2016, A1. Location in patent: Page/Page column 27; 28
[5] Tetrahedron Letters, 2010, vol. 51, # 16, p. 2170 - 2173