Synthesis Reference(s)

Journal of the American Chemical Society, 111, p. 3725, 1989 DOI: 10.1021/ja00192a034The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038Tetrahedron Letters, 34, p. 6907, 1993 DOI: 10.1016/S0040-4039(00)91827-6

Air & Water Reactions

Insoluble in water.

Reactivity Profile

O-Phthalimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). O-Phthalimide forms salts with bases.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition O-Phthalimide emits toxic fumes of nitrogen oxides.

Fire Hazard

Literature sources indicate that O-Phthalimide is combustible.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise the imide from EtOH (20mL/g) (charcoal), or sublime it. For potassium phthalimide see entry in “Metal-organic Compounds”, Chapter 5. [Beilstein 21/10 V 270.]

Definition

ChEBI: A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.

General Description

White to light tan powder. Slightly acidic.