4-BROMO-2-IODOPHENOL Chemical Properties

Melting point:

90℃ (ethanol )

Boiling point:

243.0±25.0℃ (760 Torr)

Density 

2.369±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

100.8±23.2℃

storage temp. 

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

form 

powder to crystal

pka

7.94±0.18(Predicted)

color 

White to Light yellow to Light orange

Safety Information

HS Code 

2908190090

4-BROMO-2-IODOPHENOL Usage And Synthesis

Application

4-Bromo-2-iodophenol, also known as 2-iodo-4-bromophenol, is an organic intermediate that can be prepared by nitration and reduction of p-bromophenol followed by diazotization and iodination.

Synthesis

General procedure for the synthesis of 4-bromo-2-iodophenol (4) from 2-iodophenol: 2-iodophenol (11 g, 50 mmol) was dissolved in a solvent mixture of dichloromethane (DCM, 200 mL) and methanol (MeOH, 100 mL). Subsequently, tetrabutylammonium tribromide (TBATB, 25.31 g, 52.5 mmol) was added in batches over 10 min. The reaction mixture was stirred at room temperature for 2 h before the reaction was quenched with 1N hydrochloric acid (HCl, 200 mL). The organic layer (DCM layer) was separated and the aqueous layer was extracted twice more with dichloromethane (DCM). All organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel, 50%-100% dichloromethane/hexane gradient elution) to afford the target product 4-bromo-2-iodophenol (10.2 g, 68% yield).

References

[1] Tetrahedron, 2015, vol. 71, # 35, p. 5946 - 5951
[2] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8680 - 8688
[3] Organic Letters, 2015, vol. 17, # 22, p. 5666 - 5669
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1931, vol. 192, p. 1037
[5] Canadian Journal of Chemistry, 1965, vol. 43, p. 650 - 658

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