Phthalimide

Phthalimide
Identifiers
CAS number 85-41-6 Y
PubChem 6809
ChemSpider 6550 Y
ChEBI CHEBI:38817 Y
ChEMBL CHEMBL277294 Y
Jmol-3D images Image 1
Properties[1]
Molecular formula C8H5NO2
Molar mass 147.13 g mol−1
Appearance White solid
Melting point

238 °C, 511 K, 460 °F

Boiling point

336 °C, 609 K, 637 °F (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
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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 secondary amine or ammonia. It is a white solid at room temperature.

Contents

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, which can be made by reacting phthalimide with metal carbonates. Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100 °C or with potassium hydroxide in absolute ethanol[2], 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 analog of phthalimide.[3] It is very rarely found among few burning coal fire sites.

References

  1. ^ "Phthalimide". Chemicalland21. http://www.chemicalland21.com/specialtychem/finechem/PHTHALIMIDE.htm. Retrieved 15 November 2011. 
  2. ^ "β-BROMOETHYLPHTHALIMIDE". Organic Syntheses. http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0119. Retrieved 15 November 2011. 
  3. ^ "Kladnoite". mindat.org. http://www.mindat.org/min-2222.html. Retrieved 15 November 2011.