Phthalimide

From Wikipedia, the free encyclopedia

Phthalimide
IUPAC name	Isoindole-1,3-dione
Other names	Phthalimide Phthalimidoyl (deprotonated)
Identifiers
CAS number	[85-41-6]
SMILES	O=C2NC(C1=CC=CC=C12)=O
Properties
Molecular formula	C8H5O2N1
Molar mass	147.13 g/mol
Appearance	white solid
Density	? g/cm3, ?
Melting point	238°C
Boiling point	336°C (sublimes)
Solubility in water	<0.1 g/100 ml (19.5 °C)
Acidity (pKa)	8.3
Basicity (pKb)	5.7
Viscosity	? cP at ?°C
Hazards
Flash point	?°C
Related compounds
Related Amides	Maleimide
Related compounds	Phthalic anhydride
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

Contents 1 Uses 2 Reactivity 3 References 4 External links

[edit] Uses

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

[edit] 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%.

[edit] References

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.

• Information sheet
• Organic Chemistry: Structure and Function, Fourth Edition, Copyright 2003

[edit] External links