Phthalimide

Phthalimide
IUPAC name	Isoindole-1,3-dione
Other names	Phthalimide Phthalimidoyl (deprotonated)
Identifiers
CAS number	85-41-6 Y
SMILES	O=C2NC(C1=CC=CC=C12)=O
Properties
Molecular formula	C8H5O2N1
Molar mass	147.13 g/mol
Appearance	white solid
Melting point	238 °C, 511 K, 460 °F
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
Related Amides	Maleimide
Related compounds	Phthalic anhydride
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

This article's citation style may be unclear. The references used may be made clearer with a different or consistent style of citation, footnoting, or external linking. (September 2007)

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