Phthalimide

Phthalimide

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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.

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

External links

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