Phthalimide

Phthalimide
skeletal formula of the phthalimide moleculeskeletal formula of the phthalimide molecule	ball-and-stick model of the phthalimide molecule
Names
	IUPAC name Isoindole-1,3-dione
	Other names Phthalimide Phthalimidoyl (deprotonated)
Identifiers
CAS Number	85-41-6 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.001.458
CompTox Dashboard (EPA)	DTXSID3026514 ;
	SMILES O=C2NC(C1=CC=CC=C12)=O;
Properties
Chemical formula	Template:CarbonTemplate:HydrogenTemplate:OxygenTemplate:Nitrogen
Molar mass	147.13 g/mol
Appearance	white solid
Melting point	238 °C (460 °F; 511 K)
Boiling point	336°C (sublimes)
Solubility in water	<0.1 g/100 ml (19.5 °C)
Acidity (pKa)	8.3
Basicity (pKb)	5.7
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Phthalimide is an imide, which is a chemical compound with two carbonyl groups bound to a primary amine or ammonia. It is a white solid at room temperature.

Preparation

Phthalimide can be prepared by heating phthalic anhydride with aqueous ammonia giving 95-97% yield. Alternatively, it may be prepared by fusing the anhydride with ammonium carbonate.

Uses

Phthalimide is used in plastics, in chemical synthesis, and in research.

Reactivity

It forms salts with various metals such as potassium and sodium due to its high acidity caused by the electrophilic carbonyl groups attached to the nitrogen atom, and can be made by reacting phthalimide with metal carbonates. Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100°C, is used in the Gabriel synthesis of primary amines, and the Gabriel synthesis of glycine has yields as high as 85%.

Natural occurrence

Kladnoite is a natural (mineral) analogue of phthalimide. It is very rarely found among few burning coal fire sites.

References

Information sheet
Organic Chemistry: Structure and Function, Fourth Edition, Copyright 2003
Organic Chemistry, Volume 1, Sixth Edition, I L Finar