3-broMo-5-iodo-phenol

3-broMo-5-iodo-phenol Property

Melting point:

82.5 °C

Boiling point:

324.2±32.0 °C(Predicted)

Density 

2.369±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.15±0.10(Predicted)

form 

crystalline needles

color 

Light golden brown

Safety

HS Code 

2908190090

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.

3-broMo-5-iodo-phenol Chemical Properties,Usage,Production

Uses

3-Bromo-5-iodophenol is a reactant in the preparation of N-[3-(1H-Indol-4-yl)-5-(2-methoxyisonicotinoyl)phenyl]methanesulfonamide (LP-261), a potent antimitotic agent.

Synthesis

General procedure for the synthesis of 3-bromo-5-iodophenol from 1-bromo-3-iodo-5-methoxybenzene: 1-bromo-3-iodo-5-methoxybenzene (6.29 g, 20.1 mmol) was suspended in a 33% hydrogen bromide solution in acetic acid (150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux with vigorous stirring and the reaction continued for 2 days. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane (3 × 100 mL). The organic layers were combined, washed with water (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the crude product. The crude product was purified by rapid chromatography on silica gel (300 g of silica gel, eluent ethyl acetate/heptane 1:9) to afford 3-bromo-5-iodophenol (21.2 g, 96% yield) as a light brown solid.

References

[1] Patent: US2006/270686, 2006, A1. Location in patent: Page/Page column 41
[2] Patent: US2008/280891, 2008, A1. Location in patent: Page/Page column 41
[3] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 117