PHTHALIMIDE

Phthalimide
General
Systematic name	Isoindole-1,3-dione
Other names	Phthalimide
Molecular formula
SMILES	O=C2NC(C1=CC=CC=C12)=O
Molar mass	147.13 g/mol
Appearance	white solid
CAS number	[85-41-6]
Properties
Density and phase	? g/cm3, ?
Solubility in water	<0.1 g/100 ml (19.5 °C)
Melting point	238°C
Boiling point	336°C (sublimes)
Acidity (p''K''a)	8.3
Basicity (p''K''b)	5.7
Viscosity	? cP at ?°C
Structure
Molecular shape	?
Coordination geometry	?
Crystal structure	?
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	?°C
R/S statement	R: ? S: ?
RTECS number	?
Supplementary data page
Structure and properties	''n'', εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
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)

'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

Uses

Reactivity

References

External links

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%.

References

★ Information sheet

★ Organic Chemistry: Structure and Function, Fourth Edition, Copyright 2003

External links