3-(3-IODOPHENYL)PROPIONIC ACID Chemical Properties

Boiling point:

357℃

Density 

1.775

Flash point:

170℃

storage temp. 

2-8°C(protect from light)

pka

4.59±0.10(Predicted)

Appearance

white solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2916399090

3-(3-IODOPHENYL)PROPIONIC ACID Usage And Synthesis

Uses

3-(3-iodo)phenylacetic acid can be used as a pharmaceutical synthesis intermediate and can be used in laboratory research and development processes.

Synthesis

A stirred solution of (3-aminophenyl)propionic acid (4.91 g, 29.7 mmol) in water (50 mL) and concentrated H2SO4 (4 mL) was stirred at -7 C. A solution of NaNO2 (2.4 g, 34.7 mmol) in a minimum amount of water was added to the (ice-salt bath), draining the nitrite solution below the surface of the solution and maintaining the temperature below 0C. After 10 min, the mixture was checked for the presence of excess NO2- using starch-KI indicator paper to ensure that diazotization was complete. Ether (50 mL) was added, followed by a slow addition of a solution of KI (15 g, 90 mmol) in a minimum amount of water to control the dramatic release of N2. After addition, the reactants were stirred and warmed to ambient temperature within 3 hours. The layers were separated and the aqueous layer was extracted with additional ether (2 x 50 mL). The combined ether layers were back-extracted with 5% (w/v) NaHSO3 (aqueous), brine (1 x 25 mL), dried over MgSO4, filtered and concentrated to give (3-iodo)phenylacetic acid in 8.0 g yield.

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