4-(tert-Butyl)-2-iodophenol

4-(tert-Butyl)-2-iodophenol Property

Melting point:

73-75 °C

Boiling point:

78-80 °C(Press: 0.3 Torr)

Density 

1.563±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

8.73±0.18(Predicted)

color 

White to off-white

Safety

HS Code 

2908190090

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.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

4-(tert-Butyl)-2-iodophenol Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-(tert-butyl)-2-iodophenol from 4-tert-butylphenol: A 300 mL reactor was fully displaced with nitrogen and dried, and 20.0 g (133 mmol) of 4-tert-butylphenol and 100 mL of acetic acid were added to the reactor. Subsequently 25.0 g (154 mmol) of iodine monochloride was added. The reaction mixture was heated at reflux for 7.5 hours at 120°C. Upon completion of the reaction, the reaction was quenched with aqueous sodium bisulfite. The soluble material in the reaction mixture was extracted with dichloromethane and the resulting organic phase was washed with saturated aqueous sodium bicarbonate solution and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, the solvent was removed from the filtrate by distillation and finally purified by silica gel column chromatography to give 15.4 g of reddish brown solid. Next, the reactor was again fully displaced with nitrogen and dried, to which 1.85 g (60 wt%, 46.2 mmol) of sodium hydride was added. 8.36 g of the reddish-brown solid obtained as previously described was dissolved in tetrahydrofuran and 40 mL of this solution was slowly added dropwise under water cooling for 2.5 hours. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Subsequently, 3.00 mL (39.9 mmol) of chloromethyl methyl ether was added under ice-cooled conditions and stirring was continued for 30 minutes. At the end of the reaction, the reaction was quenched by the addition of 100 mL of water, the organic layer was separated and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent in the filtrate was removed by distillation to give 9.34 g (96% yield) of the target product, compound (17).

References

[1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 7, p. 1243 - 1248
[2] Journal of Medicinal Chemistry, 1980, vol. 23, # 12, p. 1414 - 1427
[3] Tetrahedron Letters, 2008, vol. 49, # 5, p. 893 - 895
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 39, # 9, p. 711 - 729
[5] RSC Advances, 2014, vol. 4, # 12, p. 6267 - 6274